CN106188106A - Zinc complex crystal - Google Patents
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- CN106188106A CN106188106A CN201610529091.7A CN201610529091A CN106188106A CN 106188106 A CN106188106 A CN 106188106A CN 201610529091 A CN201610529091 A CN 201610529091A CN 106188106 A CN106188106 A CN 106188106A
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- zinc complex
- dichloromethane
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- 239000013078 crystal Substances 0.000 title claims abstract description 18
- 239000011701 zinc Substances 0.000 title abstract description 20
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 title abstract description 10
- 229910052725 zinc Inorganic materials 0.000 title abstract description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 32
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims abstract description 25
- 238000006243 chemical reaction Methods 0.000 claims abstract description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 10
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 9
- 239000003208 petroleum Substances 0.000 claims abstract description 6
- 239000002904 solvent Substances 0.000 claims abstract description 6
- QRUBYZBWAOOHSV-UHFFFAOYSA-M silver trifluoromethanesulfonate Chemical compound [Ag+].[O-]S(=O)(=O)C(F)(F)F QRUBYZBWAOOHSV-UHFFFAOYSA-M 0.000 claims abstract description 5
- 239000012047 saturated solution Substances 0.000 claims abstract description 4
- 238000000926 separation method Methods 0.000 claims abstract 2
- 238000002360 preparation method Methods 0.000 claims description 7
- 238000010189 synthetic method Methods 0.000 claims description 5
- 238000002447 crystallographic data Methods 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 230000005260 alpha ray Effects 0.000 claims 1
- 229910002804 graphite Inorganic materials 0.000 claims 1
- 239000010439 graphite Substances 0.000 claims 1
- 238000001914 filtration Methods 0.000 abstract 1
- 238000001308 synthesis method Methods 0.000 abstract 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 9
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- -1 mercury ions Chemical class 0.000 description 4
- 229910052697 platinum Inorganic materials 0.000 description 4
- 238000004364 calculation method Methods 0.000 description 3
- CLSUSRZJUQMOHH-UHFFFAOYSA-L platinum dichloride Chemical compound Cl[Pt]Cl CLSUSRZJUQMOHH-UHFFFAOYSA-L 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000012937 correction Methods 0.000 description 2
- GZAJJDUWYRDMPO-UHFFFAOYSA-N methylsulfinylmethane;platinum Chemical compound [Pt].CS(C)=O GZAJJDUWYRDMPO-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 125000002524 organometallic group Chemical group 0.000 description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
- HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- VPSSPAXIFBTOHY-LURJTMIESA-N (2s)-2-amino-4-methylpentan-1-ol Chemical compound CC(C)C[C@H](N)CO VPSSPAXIFBTOHY-LURJTMIESA-N 0.000 description 1
- 208000035126 Facies Diseases 0.000 description 1
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 1
- 238000004873 anchoring Methods 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- CZKMPDNXOGQMFW-UHFFFAOYSA-N chloro(triethyl)germane Chemical compound CC[Ge](Cl)(CC)CC CZKMPDNXOGQMFW-UHFFFAOYSA-N 0.000 description 1
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical class ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 229920001795 coordination polymer Polymers 0.000 description 1
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
- 235000018417 cysteine Nutrition 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000002050 diffraction method Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
- 238000000302 molecular modelling Methods 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000004424 polypyridyl Polymers 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 229940127224 quinoline drug Drugs 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003303 ruthenium Chemical class 0.000 description 1
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- NLDYACGHTUPAQU-UHFFFAOYSA-N tetracyanoethylene Chemical compound N#CC(C#N)=C(C#N)C#N NLDYACGHTUPAQU-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/06—Zinc compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
Abstract
A zinc complex crystal has the following structural formula:(I) is provided. The synthesis method of the zinc complex crystal comprises synthesis and separation, wherein 1.0g of Pt (DMSO) is weighed in the synthesis2Cl2Dissolving the zinc complex by using 30mL of dichloromethane as a solvent, adding 0.6g of AgOTf, keeping out of the sun, reacting for 48 hours at room temperature, adding 0.2998 of zinc complex, continuing to react for 2 days, stopping the reaction, filtering, preparing a saturated solution by using dichloromethane/petroleum ether with the volume ratio of 1/1, and naturally volatilizing to obtain the novel zinc complex single crystal.
Description
One, technical field
The present invention relates to a kind of organometallic complex (coordination compound) and preparation method thereof, particularly to organic containing sulfur metal
Coordination compound and preparation method thereof, is exactly a kind of dimethyl sulfoxide platinum complex crystal and synthetic method thereof.
Two, background technology
Metal platinum complex has caused people's because of it in anticancer and the aspect such as molecular magnet, fluorescent material potential using value
Extensive concern.The synthetic method of metal platinum complex has many documents to report in recent years.【1-7】
1. A Comparative Antimicrobial Study In Between a Quinoline Drug and Its
Complexes: Spectral, Kinetic, and Molecular Modeling Investigations, Al-
Hazmi, Gamil A. A.; Saad, Fawaz A. Synthesis and Reactivity in Inorganic,
Metal-Organic, and Nano-Metal Chemistry (2015), 45(11), 1743-1757.
2. One-pot synthesis of dual-emitting BSA-Pt-Au bimetallic
nanoclusters for fluorescence ratiometric detection of mercury ions and
cysteine, Ding, Shou-Nian; Guo, Yun-Xia
From Analytical Methods (2015), 7(14), 5787-5793.
3. Five coordinate platinum(II) in [Pt(bpy)(cod)(Me)][SbF6]: a
structural and spectroscopic study, Klein, Axel; Neugebauer, Michael; Krest,
Alexander; Luening, Anna; Garbe, Simon; Arefyeva, Natalia; Schloerer, Nils ,
Inorganics (2015), 3(2), 118-138.
4. Synthesis and Reactivity of Platinum(II) cis-Dialkyl, cis-Alkyl
Chloro, and cis-Alkyl Hydrido Bis-N-heterocyclic Carbene Chelate Complexes
, Brendel, Matthias; Engelke, Rene; Desai, Vidya G.; Rominger, Frank;
Hofmann, Peter , Organometallics (2015), 34(12), 2870-2878.
5. The Challenge of Deciphering Linkage Isomers in Mixtures of Oligomeric
Complexes Derived from 9-Methyladenine and trans-(NH3)2PtII Units, Ibanez,
Susana; Mihaly, Bela; Sanz Miguel, Pablo J.; Steinborn, Dirk; Pretzer, Irene;
Hiller, Wolf; Lippert, Bernhard
Chemistry - A European Journal (2015), 21(15), 5794-5806.
6. Polypyridyl ruthenium complexes containing anchoring nitrile groups as
TiO2 sensitizers for application in solar cells , Mecchia Ortiz, Juan H.;
Longo, Claudia; Katz, Nestor E. Inorganic Chemistry Communications (2015),
55, 69-72.
7. Charge-bistable Pd(III)/Pd(II,IV) coordination polymers: phase
transitions and their applications to optical properties, Kumagai, Shohei;
Takaishi, Shinya; Iguchi, Hiroaki; Yamashita, Masahiro , Dalton Transactions
(2015), 44(18), 8590-8599。
Three, summary of the invention
It is desirable to provide a kind of Pt-O metal organic complex is to be applied to catalytic field, technical problem to be solved is selected for a post
Dimethyl sulfoxide is selected as part and to synthesize dimethyl sulfoxide Zn complex.
Platinum complex alleged by the present invention is a kind of be by dimethyl sulfoxide and platinous chloride prepare by shown in below formula
Coordination compound:
(I).
Chemical name: dimethyl sulfoxide trifluoromethanesulfonic acid two hydrated zinc coordination compound, is called for short coordination compound (I).
This coordination compound shows preferable catalytic performance in the nitrile silicification reaction of benzaldehyde, and its conversion ratio is up to 99 %.
This synthetic method includes synthesis and separates, and described synthesis weighs 1.0gPt (DMSO)2Cl2, use 30mL dichloromethane
Make solvent to dissolve, add AgOTf 0.6g, react 48 hours under lucifuge room temperature, add 0.2998 Zn complex, continue reaction
After 2 days, stopped reaction, filter, be 1/1 preparation saturated solution by dichloromethane/petroleum ether volume ratio, naturally volatilize a kind of newly
Zn complex monocrystalline.
Synthetic reaction is as follows:
This synthetic method one step obtains target product, and technique is simple, easy to operate.
The reaction mechanism of this reaction can be speculated as at Pt (DMSO)2Cl2With course of reaction under AgOTf lucifuge room temperature, then add
Steam effect in zinc and DMSO and silver trifluoromethanesulfonate and air in Zn complex, define a kind of Zn complex rather than
Targeted platinum coordination compound.
Four, accompanying drawing explanation
The X-diffraction analysis figure of Fig. 1 dimethyl sulfoxide trifluoromethanesulfonic acid two hydrated zinc complex crystal.
Five, detailed description of the invention
1. platinous chloride dimethyl sulfoxide coordination compound
In 100mL two-mouth bottle, add platinous chloride 1.2042g, 10mLDMSO, dichloromethane 30mL, mixture is refluxed
60h, stopped reaction, static, obtain dimethyl sulfoxide platinum complex solid, productivity 45%；Elementary analysis: test value: C:11.78
%, H: 2.91%;Value of calculation: C:11.38%, H 2.86%;IR (KBr): 1157,1134,450,430.
2. the synthesis of Zn complex:
The preparation of double-(4-isobutyl group-4,5-dihydro-2-oxazoline base)-acetonitrile Zn complex
In 100mL two-mouth bottle, under the conditions of anhydrous and oxygen-free, add anhydrous ZnCl2 0.45g (3.30mmol), 40mL chlorobenzene,
1,1,2,2-tetracyanoethene 1.0g (7.81mmol), L-leucinol 4g, at high temperature reflux 24h by mixture, stopped reaction, reduce pressure with
Remove solvent, by residue water dissolution, and use CHCl3(20mLx2) extraction, organic facies anhydrous sodium sulfate is dried, and rotates
Remove solvent, by thick product petroleum ether/dichloromethane (4:1) column chromatography, obtain white crystal, productivity 32%；[a]5 D=+
166.33º (c=0.30, CH2Cl2):1HNMR (500MHz, CDCl3, 27℃), δ (ppm) = 4.60(t, J=
0.5Hz, 4H), 3.94～4.05 (m, 8H), 1.29～1.72 (m, 12H), 0.89～0.93 (m, 24H);13C
NMR (75 MHz, CDCl3) 170.1(x2), 118.3(x2), 73.0(x4), 61.7(x4), 45.6(x4), 24.9
(x4), 22.3(x4), 21.8(x8)。IR :3439(s), 2955(s), 2927(w), 2871(w), 2201(s),
1611(s), 1530(s), 1430(s), 1386(w), 1368(m), 1342(w), 1281(w), 1260(m), 1239
(w), 1218 (w), 1133 (w), 1068 (s), 1048 (m), 951 (m), 746 (m) elementary analysis: C:59.32%, H:
7.46%, N:13.37%；Value of calculation: C:59.48%, H 7.49%, N:13.01%；
3. the preparation of dimethyl sulfoxide trifluoromethanesulfonic acid two hydrated zinc complex crystal
With weighing 1.0gPt (DMSO) in two-mouth bottle2Cl2, make solvent with 30mL dichloromethane and dissolve, add AgOTf 0.6g,
After reacting 48 hours under lucifuge room temperature, add 0.2998g Zn complex, after continuing reaction 2 days, stopped reaction, filters, with two
Chloromethanes/petroleum ether volume ratio is 1/1 preparation saturated solution, and volatilize to obtain a kind of new Zn complex monocrystalline naturally；Productivity 35%,
Fusing point: 78-80 ° of C;Elementary analysis: test value: C:12.62 %, H:2.97%;Value of calculation: C:12.97%, H
2.90%；IR (KBr): 3466,2960,2260,1623,1501,1467,1404,1369,1260,1172,
1104, 1034, 952,764, 644, 578, 520;Match crystal volume data is as follows:
Empirical formula C6H16O10F6ZnS4
Molecular weight 555.80
Temperature 100.00 (10) K
Wavelength 0.71073
Crystallographic system, Space group Monoclinic system, P21/c
Cell parameter a=5.2939 (2) α=90 °.
B=12.0096 (4) β=90.120(3) °.
c = 15.0457(4) Å γ = 90 °.
Volume 956.57(5) ^3
Charge density 2,1.930Mg/m^3
Absorption correction parameter 1.819 mm^-1
Number of electrons 560.0 in unit cell
Crystal size 0.36 x 0.1x 0.05mm
Scope 7.306 to 60.962 at Theta angle
Index capture range-7≤h≤5 of HKL ,-16 < k < 15 ,-20 < l≤19
Collection/independent diffraction data 8457/ 2588 [R (int)=0.0325]
The data integrity degree 100.0% of theta=30.5
The method Multi Slice Mode of absorption correction
Transmitance 0.70and-0.76 of minimax
The Matrix least square method of method F^2 that refine uses
Number/number of parameters 2588/0/127 that data number/use limits
The method 1.066 that refine uses
The concordance factor R 1=0.0329 of point diffraction, ω R2=0.0711
The identical factor R 1=0.0401 of observable diffraction, ω R2=0.0750
Maximum summit on difference Fourier figure and peak valley 0.697 and-0.652e. ^-3
Crystal typical bond distance data:
Crystal typical bond angle data:
(3), nitrile silicification reaction application
2-phenyl-2-(three silyloxy) propionitrile
0.1mmol coordination compound I, benzaldehyde 0.1mL, TMSCN 0.3 ml (3.3mmol), 2mL THF, in succession 30 ~
Add under 35 C, after 24 hours, add shrend and go out after post layer (petroleum ether/dichloromethane: 5/1), obtain colourless oil liquid,
Conversion ratio: > 99%;1H NMR (300MHz, CDCl3) 7.56–7.59 (m, 0.9 Hz, 2H), 7.31–7.34 (m,
3H), 5.43 (s, 1H), 0.16 (s, 9H). 13C NMR (75 MHz, CDCl3) 136.1, 128.8(x2),
126.2(x2), 119.1, 63.5, -0.39(x3)。
Claims (3)
1. a Zn complex crystal, its structural formula is as follows:
(I).
2. the Zn complex crystal described in claim 1, at a temperature of 100.00 (10) K, at Oxford X-ray single crystal diffraction
On instrument, collect diffraction data with the MoK alpha ray (λ=0.71073) through graphite monochromator monochromatization with ω-θ scan mode,
It is characterized in that crystal belongs to monoclinic system, P21/c;Cell parameter: a=5.2939 (2), α=90 °; b =
12.0096 (4), β=90.120(3) °;C=15.0457 (4), γ=90 °.
3. the synthetic method of the Zn complex crystal described in claim 1, including synthesis and separation, described synthesis is to weigh
1.0gPt(DMSO)2Cl2, make solvent with 30mL dichloromethane and dissolve, add AgOTf 0.6g, react 48 under lucifuge room temperature little
Time, add 0.2998 Zn complex, after continuing reaction 2 days, stopped reaction, filters, by dichloromethane/petroleum ether volume ratio is
1/1 preparation saturated solution, volatilize to obtain a kind of new Zn complex monocrystalline naturally.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105085578A (en) * | 2015-08-28 | 2015-11-25 | 合肥祥晨化工有限公司 | Platinum complex crystal |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1314333A (en) * | 2001-03-23 | 2001-09-26 | 中国科学院上海有机化学研究所 | Method for asymmetrically synthesizing secondary propiolic alcohol compound |
| CN105130834A (en) * | 2015-09-30 | 2015-12-09 | 中国科学院兰州化学物理研究所 | Preparation method of beta-amido-alpha-amino-acid ester derivative |
-
2016
- 2016-07-06 CN CN201610529091.7A patent/CN106188106A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1314333A (en) * | 2001-03-23 | 2001-09-26 | 中国科学院上海有机化学研究所 | Method for asymmetrically synthesizing secondary propiolic alcohol compound |
| CN105130834A (en) * | 2015-09-30 | 2015-12-09 | 中国科学院兰州化学物理研究所 | Preparation method of beta-amido-alpha-amino-acid ester derivative |
Non-Patent Citations (2)
| Title |
|---|
| ANDREY S. SMIRNOV ET AL.: "Novel (cyanamide)ZnII complexes and zinc(II)-mediated hydration of the cyanamide ligands", 《DALTON TRANSACTIONS》 * |
| STEPHAN ENTHALER ET AL.: "Deoxygenation of Sulfoxides to Sulfides in the Presence of ZincCatalysts and Boranes as Reducing Reagents", 《CATALYSIS LETTERS》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105085578A (en) * | 2015-08-28 | 2015-11-25 | 合肥祥晨化工有限公司 | Platinum complex crystal |
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