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2016 Vol. 24, No. 2
Published: 2016-02-20
93
Synthesis of Novel Chiral Thioureas Derived from D-mannitol and Their Application in Henry Reaction
LIU Miao-xi, WANG Xiao-gang, HE Wei, LIU Peng
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.02.15343
An intermediate of chiral amine with 1,3-dioxane structure(
4
) was obtained by a four-step reaction of condensation, alcoholysis, azidation and reduction, using D-mannitol as material. Three novel chiral thioureas(
6a~6c
) were synthesized by the reaction of
4
with 3,5-bis(trifluoromethyl)phenyl isothiocyanate, epiquinine isothiocyanate and quinidine isothiocyanate, respectively. The structures were characterized by
1
H NMR,
13
C NMR, IR and HR-MS. The catalytic performances and selectivities of
6
were investigated by Henry reaction of nitrocarbol with benzaldehyde. The results showed that the yield and enantioselectivity of (
S
)-2-nitrophenylethan-1-ol were 69% and 78%, respectively, using Et
3
N as base, toluene as solvent, 5 mol%
6b
as catalyst at -30 ℃ for 24 h.
2016 Vol. 24 (2): 93-97 [
Abstract
] (
434
)
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(1 KB)
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(502 KB) (
726
)
98
Synthesis and Flame Retardant Properties of A Novel Phosphorouscontaining Flame Retardant DOPOPPO
HAN Ming-xuan, XU Miao-jun, LI Bin
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.02.15031
A novel phosphorus-containing flame retardant, bis［4-(methylene-hydroxy-DOPO)phenoxy］phenyl phosphine oxide(DOPO-PPO), was synthesized from phenylphosphonic dichloride,
p-
hydroxybenzaldehyde and 6
H
-dibenz［
c,e
］［1,2］oxaphosphorin 6-oxide(DOPO). The structure was characterized by
1
H NMR and IR. The thermal stability, thermal degradation behavior and charring property of DOPO-PPO were investigated by TGA and DTG. The results showed that the initial thermal decomposition temperature of DOPO-PPO was 210 ℃ and the char yield was 30.4% at 700 ℃. A flame retardant epoxy resin(
3
) was prepared, using epoxy resin as base material, DOPO-PPO as flame retardant and 4,4′-diaminodiphenylsulfone as curing agent. The flame retardant properties of
3
were investigated by limiting oxygen index(LOI) and vertical burning(UL-94) test. The results showed that the LOI of
3
12
(dosage of DOPO-PPO was 12.0
wt
%) was 34.0% with flammability rating V-0.
2016 Vol. 24 (2): 98-101 [
Abstract
] (
428
)
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(1 KB)
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(557 KB) (
621
)
102
In-situ
Synthesis and Fluorescence Properties of A Novel Mononuclear Nickel Complex
LI Gui, ZHANG Jing-ling, WANG Ji-ming, ZHANG Shu-hua
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.02.15076
A novel mononuclear Schiff base complex, Ni(L){
1
, H
3
L=(3,5-dicloro-2-hydroxy-benzylidene)［N′-(3,5-dicloro-2-hydroxy-benzylidene)］-1-amino-
N
-aminoformimidic acid}, was synthesized through solvothermal
in-situ
synthesis method, using 3,5-dichloro-salicylaldehyde and carbohydrazide as raw materials, DMF and acetonitrile as solvent, nickel nitrate as ion source. The structure was characterized by FTIR, elemental analysis and single-crystal diffraction.
1
(CCDC: 1 044 165) belongs to monoclinic system and space group
P2
1
/m. The cell parameters of
1
were
a
=10.416 6(5) ，
b
=6.516 2(3) ，
c
=13.479 1(6) ，
β
=109.330(5)°，
V
=863.34(7)
3
，
Z
=2，
Dc
=1.834 g·cm
-3
，
μ
=1.764 mm
-1
，
F
(000)=474. Nickel(III) was coordinated with two nitrogen atoms and two oxygen atoms from L
3-
to form a rectangle-plane. The fluorescence property of
1
was investigated by FL. The result showed that
1
exhibited strong fluorescent property around 500 nm upon an excitation band at 435 nm in DMF.
2016 Vol. 24 (2): 102-106 [
Abstract
] (
529
)
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(1 KB)
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(589 KB) (
394
)
107
Synthesis of A Novel P－N－Si Halogen-free Flame Retardant and Its Application in Cotton Fiber
DOU Wu-hong, LIU Dong-yue, WANG Wen-tao, ZHAO Bin, LIU Ya-qing
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.02.15333
A novel ternary integrated P－N－Si halogen-free flame retardant, phenoxy-bis-(triethoxysilylpropyl)phosphamide(
3
), was synthesized by the reaction of phenylphosphonic dichloride(
1
) with (3-aminopropyl)triethoxysilane(
2
). The structure was characterized by
1
H NMR，
31
P NMR and FT-IR. Effects of solvent, reaction temperature, reaction time, acid-blinding agent and molar ratio{
r
［n(
2
) ：
n
(
1
)］} on the yield of
3
were investigated. The results showed that the optimum reaction condition at 40 ℃ for 6 h were as followed:
1
was 8 mmol,
r
was 2.4, THF was solvent and trithylamine was acid-blinding agent. The yield of
3
was 88.2% under the optimum reaction conditions. The flame retardant property of
3
was characterized by TGA. The results indicated that the initial decomposition temperature of
3
was 150 ℃ and the char residue is about 14.6% at 600 ℃. Cotton fabrics(
c
) were treated with
3
. The char residue of
c-3
15
(the mass portion of
3
was 15% in
c
) at 600 ℃ was 33.4%, which was better than
c
(7.6%).
2016 Vol. 24 (2): 107-111 [
Abstract
] (
322
)
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(1 KB)
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(660 KB) (
308
)
112
Preparation of H
3
PO
4
/MCM-41-T Catalysts and Their Applicationon in Gas Phase Dehydration of Glycerol to Acrolein
MA Tian-lin, ZHU Ye-nan, SHAO Rong, YUN Zhi, DING Jian-fei
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.02.15364
A series of H
3
PO
4
/MCM-41 catalysts at different calcination temperature(
1
-T) were prepared by impregnation method. The structures were characterized by FT-IR, XRD and N
2
adsorption-desorption. The catalytic activities of
1
-T were investigated by gas phase dehydration of glycerol to acrolein. The results indicated that
1
450
had higher proportion of Brnsted acidic sites, which exhibited best catalytic activity with 94% conversion of glycerol, 77% yield of acrolein and 82% selectivity of acrolein.
2016 Vol. 24 (2): 112-114 [
Abstract
] (
336
)
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(1 KB)
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(465 KB) (
315
)
115
Synthesis and Thermal Stability of A Novel P－N Organometallic Flame Retardant
XIONG Kuan-kuan, WANG Wen-tao, ZHAO Bin, LIU Ya-qing
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.02.15372
N
-(diphenylphosphino)-1,1-diphenyl-
N
-(3-(triethoxysilyl)propyl)phosphinamine(
3
) was prepared by substitution reaction of
γ
-aminopropyl triethoxysilane(
1
) with chlorodiphenyl phosphine(
2
). A novel P－N organometallic flame retardant(
5
) was synthesized by the reaction of
3
with nickel chloride hexahydrate(
4
). The structures were characterized by
1
H NMR,
31
P NMR and FT-IR. Effects of molar ratio［
r
=
n
(
2
) :
n
(
1
)］, solvent, reaction time and reaction temperature on the yield of
3
were investigated. The optimum reaction conditions were as followed: dichloromethane was solvent,
1
was 19 mmol,
r
was 2.3, reacted at 25 ℃ for 14 h. The yield of
3
was 89.5% under the optimum conditions. TGA results showed that the initial decomposition temperature of
5
was 252 ℃ and the char yield was about 31.9% at 700 ℃.
2016 Vol. 24 (2): 115-119 [
Abstract
] (
402
)
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(1 KB)
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(575 KB) (
356
)
120
Synthesis of Novel Matrine Derivatives Containing Naphthalene Structure
YANG Fang-fang, LIANG Peng-yun, ZHOU Zhong-jie, LIU Xu, YANG Hua, WANG Li-sheng
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.02.15085
Ten novel matrine derivatives containing naphthalene structure, 14-naphthalene hydroxyl methyl matrine(
3a~3c
), 14-naphthalene formyl matrine(
3g~3j
) and 14-naphthyl methyl alkenyl matrine(
3d~3f
), were designed and synthesized by reaction of matrine and naphthalene compounds in THF, using LDA and NaH as nucleophilic reagent. The structures were characterized by
1
H NMR,
13
C NMR, FT-IR and ESI-MS.
2016 Vol. 24 (2): 120-123 [
Abstract
] (
324
)
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(1 KB)
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(428 KB) (
337
)
124
Preparation and Hg
2+
Adsorption Properties of Thiol Functionalized Mesoporous Materials
SONG Bo, LI Yun-ping, WANG Chun, WANG An
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.02.15078
A series of thiol functionalized mesoporous materials(SBA-SH-x) with different thiol ratio［x=n(MPTES)/
n
(TEOS+MPTES)］ were prepared by copolymerization of hydrolyzed TEOS and MPTES in acid condition, using tri-block non-ionic surfactant P123 as template. The structures and properties were characterized by FT-IR, elemental analysis, SEM, TEM, small angle X-ray and N
2
adsorptiondesorption. The results showed that x＜10%, SBA-SH-x were hexagonal
p6mm
mesophase; 10%＜x＜15%, SBA-SH-x were cubic
Ia3d
mesophase; x＞20%, SBA-SH-x were in disorder structure. Further increase of thiol contents resulted in slatted or non-mesoporous materials. The results of Hg
2+
adsorption in water indicated that SBA-SH-10 and SBA-SH-15 exhibited good adsorption properties.
2016 Vol. 24 (2): 124-129 [
Abstract
] (
521
)
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(1 KB)
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(1245 KB) (
448
)
130
Synthesis of A Novel Tetracationic 1,2,3-Triazolium Cyclophane
DUAN Qun-peng, LU Kui
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.02.15371
An intermediate, 4,4′-［4,6-bis(hexyloxy)-1,3-phenylene］bis｛1-［4-(azidomethyl)benzyl］- 1
H
-1,2,3-triazole｝(
6
), was prepared by a five-step reaction from resorcinol. 1,2,3-Triazolophane(
7
) was obtained by Click reaction of
6
with 1,5-diethynyl-2,4-bis(hexyloxy)benzene under pseudo-high dilution conditions. A novel tetramethylated 1,2,3-triazolium-phane was synthesized by the reaction of trimethyloxonium tetrafluoroborate with
7
. The structure was characterized by
1
H NMR，
13
C NMR and HR-ESI-MS.
2016 Vol. 24 (2): 130-133 [
Abstract
] (
318
)
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(1 KB)
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(545 KB) (
270
)
134
Synthesis of Novel Allylic Ether Compounds Catalysed by FeCl
3
XU Xing-zhu, GU Zhan-shou, LI Zheng-yi, SUN Xiao-qiang, WANG Zhi-ming
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.02.15084
Nine allylic ether compounds(
2a~2i
;
2c
,
2e~2i
were novel compounds) were synthesized by intermolecular nucleophilic substitution reaction, using allylic alcohols(
1a~1i
) and ethanol as starting materials, FeCl
3
as catalyst. The yields of
2a~2i
were 80%~95%. The structures were characterized by
1
H NMR,
13
C NMR and HR-ESI-MS. Effects of catalyst, solvent, reaction temperature and time on yield of
2a
were investigated. The results showed that the yield of 2
a
was 95% under the optimized reaction conditions［
1a
0.5 mmol, FeCl
3
4 mg, EtOH 2.5 mmol, CH
2
Cl
2
as solvent， reacted at rt for 0.8 h］.
2016 Vol. 24 (2): 134-138 [
Abstract
] (
292
)
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(1 KB)
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(397 KB) (
349
)
139
Synthesis and Photocatalytic Performance of A Novel Keggin Compound ｛［Et
3
N］
5
［H
3
BW
12
O
40
］2·2H
2
O｝
SHI Shu-yun
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.02.15133
A novel polyoxometalate, ［Et
3
N］
5
［H
3
BW
12
O
40
］
2
·2H
2
O(
1
,
CCDC: 932 982), was prepared by hydrothermal method, using Et
3
N, Na
2
WO
4·
2H
2
O, H
3
BO
4
and Cu(NO
3
)
2
as materials. The structure and properties were characterized by UV-Vis, FT-IR, elemental analysis, XRD, XPS, TGA and CV. The results showed that
1
was in 3D supramolecular structure. The weight loss ratio of
1
was 15.53% at 602 ℃. The results of
1
catalytic degradation methyl orange indicated that
1
exhibited good photocatalytic property. The degradation ratio decreased to 41.6% from 100% with degradation rate of 11.68%·h
-1
.
2016 Vol. 24 (2): 139-143 [
Abstract
] (
299
)
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(1 KB)
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(864 KB) (
358
)
144
Synthesis and GTPγS Binding Activity of Novel 2-Bromo-benzamides Small Molecule CCR5 Antagonists
CHENG De-jun, HUANG Bin, Yang Guo
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.02.15358
5-Bromo-1-［(4-chlorobenzyl)oxy］-2-bromotoluene(
3
) was obtained by substitution reaction, reduction and NBS bromination from 5-bromo-2-hydroxybenzaldehyde.
N
-allyl-2-bromo-
N
-(4-piperidinyl)benzamide(
7
) was prepared by protection, reduction and condensation reaction from 4-piperidone-hydrochlorid. A novel non-peptide small molecule compound,
N
-allyl-2-bromo-
N
-【1-{2-［(4-chlorobenz)oxyyl］-5-bromobenz}-4-piperidin】 benzamide(
8
) with total yield of 32.5%, was synthesized by substitution reaction of
3
with
7
. The structure was characterized by
1
H NMR，
13
C NMR， IR and ESI-MS. The biological activity of
8
was detected by the SPA GTP
γ
S assay. The results indicated that the biological binding activity of
8
approach to TD0232 with IC
50
of (8.12±0.3) nmol·L
-1
.
2016 Vol. 24 (2): 144-147 [
Abstract
] (
286
)
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(1 KB)
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(660 KB) (
299
)
148
Synthesis and Antibacterial Activities of Novel Vanillin Benzimidazole Schiff Bases
DENG Ping, WU Min
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.02.15260
Three novel vanillin benzimidazole Schiff bases(
5a~5c
) were synthesized, using
o
-phenylenediamine and vanillin as raw materials. The structures were characterized by
1
H NMR and IR. The antibacterial activities of
5a~5c
against
Fusarium oxysporium
(
F.oxy
),
Alternaria solani
(
A.sol
),
Fusarium graminearum
(
F.gra
),
Cercospora sorghi
(
C.sor
) and
Fusaurium oxysporiumf. sp. vasinfectum
(
F.oxy
) were investigated by mycelial growth rate method. The results indicated that
5c
exhibited better antimicrobial activities against
F.gra, F.ox
and
C.sor
than Carbendazim with EC
50
of 19.76 mg·L
-1
， 24.94 mg·L
-1
and 29.15 mg·L
-1
.
2016 Vol. 24 (2): 148-151 [
Abstract
] (
499
)
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(1 KB)
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(486 KB) (
1874
)
152
Preparation of Novel Nano-catalyst Pd/g-C3N4NSs and Its Application in Suzuki-Miyaura Reaction
SU Xiang-yang， ZHONG Lin
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.02.15081
A novel 2D nano-catalyst, Pd/g-C
3
N
4
NSs(
1
), was prepared by supporting nano-Pd on g-C
3
N
4
NSs via one-step method. The structure and morphology were characterized by TEM, XRD and XPS. The catalytic properties of
1
were investigated by Suzuki-Miyaura reaction of aryl halide with substituted phenylboronic acid. The results showed that
1
exhibited good catalytic property with 53 000 h
-1
of TOF. Yield of partial products were over 99% and the catalytic performance of
1
remain stable after cycling for three times.
2016 Vol. 24 (2): 152-154 [
Abstract
] (
316
)
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(1 KB)
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(466 KB) (
377
)
155
Process Improvement on Synthesis of STAT3 Inhibitor(HO-3867)
SU Jin-cai， WENG Zhi-bing， ZHOU Guo-chun
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.02.15304
Methyl 1-oxyl-2,2,5,5-tetramethylpyrroline-3-carboxylate(
5a
) was prepared by one-pot method of Favorskii reaction and oxidation, using 3,5-dibromo-2,2,6,6-tetramethylpiperidin-4-one as starting material. 3-Hydroxymethyl-1-oxy-2,2,5,5-tetramethyl pyrroline(
7
) was obtained by low temperature reduction reaction of
5a
, using LiAlH
4
as reducing agent. HO-3867 was synthesized by semi-continuous method of alkylation reaction of brominized
7
with arylamine. The total yield was 46.3%. The structure was confirmed by
1
H NMR and HR-ESI-MS.
2016 Vol. 24 (2): 155-159 [
Abstract
] (
783
)
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(1 KB)
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(685 KB) (
2749
)
160
Synthesis and Cytotoxicity of A Novel
O
6
-benzylguanine Derivative
LI Si-si, PENG Rui-zeng
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.02.15080
A novel
O
6
-benzylguanine(
O
6
-BG) derivative, 4-nitrobenzyl-［6-(benzyloxy)-9
H
-purin-2-yl］carbamate(
4
), was synthesized by a four-step reaction, using O
6
-BG as starting material. The structure was characterized by
1
H NMR and HR-ESI-MS. The cytotoxicities of
4
were investigated by CCK-8 method. The results indicated that
4
exhibited better inhibition activities against human glioma cell lines(SF126, SF763 and SF767) with ACUN than
O
6
-BG under hypoxia conditions. IC
50
of
4
against SF126, SF763 and SF767 were 0.04 mM, 0.1 mM and 0.03 mM, respectively.
2016 Vol. 24 (2): 160-163 [
Abstract
] (
350
)
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(1 KB)
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(461 KB) (
358
)
164
Synthesis of Novel Bis(substituted-benzylidene)acetones
GAO Fu-xing, WANG Nan-nan, GUO Peng, WANG Yong-hong, XUE Ling-fen
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.02.15309
Ten novel bis(substituted-benzylidene)acetone compounds(
2a~2j
) were synthesized at room temperature by Claisen-Schmidt condensation reaction of substituted-benzaldehyde or substituted-salicylaldehyde with acetone, respectively, using dilute sodium hydroxide as catalyst. The structures were characterized by
1
H NMR， IR, ESI-MS and elemental analysis.
2016 Vol. 24 (2): 164-166 [
Abstract
] (
579
)
HTML
(1 KB)
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(489 KB) (
433
)
167
Synthesis of Polysubstituted
β
-Carboline by Improved Cadogan Reaction
ZHONG Zheng, WANG Xin-ling, FENG Wei-sheng, YANG Huai-xia, ZHANG Jing-yu， SUN De-mei
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.02.15335
Five polysubstituted
β-
carbolines(
3a~3e
) were synthesized by improved Cadogan reaction, using phenylnitro pyridine(
2a~2e
) as precursors, P(Ph)
3
as reductant and DMAc as solvent. The structures were confirmed by
1
H NMR and HR-ESI-MS. The yields of
3a~3e
were 45%~85%, under the optimized conditions［
2
4 mmol, PPh
3
10 mmol, DMAc 5 mL, reacted at 170 ℃ for 16 h］, respectively.
2016 Vol. 24 (2): 167-169 [
Abstract
] (
296
)
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(1 KB)
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(313 KB) (
279
)
170
Synthesis of Impurity of Fosfluconazole——2-(2,4-Difluorophenyl)-1-(1
H
-1,2,4-triazol-1-yl)-3-(4
H
-1,2,4-triazol-4-yl)propan-2-yl Dihydrogen Phosphate
ZHANG You-guo, LI Qiang, HUANG Yi,ZHENG Ren-lin, YUAN Xiao-hong, LI Liang-chun
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.02.15370
The main impurity of Fosfluconazole, 2-(2,4-difluoro-Phenyl)-1-(1
H
-1,2,4-triazol-1-yl)-3-(4
H
-1,2,4-triazol-4-yl)propan-2-yl dihydrogen phosphateoxalate with purity of 98% and total yield of 7.8%, was synthesized by a seven-step reaction of Friedel－Crafts reaction, nucleophilic substitution, Corey－Chaykovsky reaction, phosphorylation and catalytic hydrogenation, using 1,3-difluorobenzene as starting material. The structure was confirmed by
1
H NMR.
2016 Vol. 24 (2): 170-173 [
Abstract
] (
401
)
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(1 KB)
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(474 KB) (
349
)
174
Process Improvement on the Synthesis of Progesterone
WU Qing-an, XU Zhi-chao, BAI Ting
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.02.15036
Stigmasterol(
1
) was separated from phytosterol. The intermediate, 3-ketobisnor-4-cholenaldehyde(
3
) was prepared through oppenauer oxidation and ozonation from
1
. Progesterone was synthesized by addition-condensation and oxygenation catalyzed by cuprous chloride from
3
. The overall yield was 69.1%. The structure was confirmed by
1
H NMR and ESI-MS.
2016 Vol. 24 (2): 174-177 [
Abstract
] (
744
)
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(1 KB)
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(547 KB) (
539
)
178
Research Progress on Total Synthesis of Maoecrystal V
YANG Lu, HUANG Rui-lei, WANG Zhi-song, YU Nie-fang
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.02.15369
Four total synthesis methods and the development of Maoecrystal V were reviewed and prospected with 30 references.
2016 Vol. 24 (2): 178-184 [
Abstract
] (
719
)
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(1 KB)
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(1328 KB) (
397
)
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