CN105061517B - A kind of preparation of chiral platinum complex crystal and synthetic method - Google Patents

A kind of preparation of chiral platinum complex crystal and synthetic method Download PDF

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CN105061517B
CN105061517B CN201510579019.0A CN201510579019A CN105061517B CN 105061517 B CN105061517 B CN 105061517B CN 201510579019 A CN201510579019 A CN 201510579019A CN 105061517 B CN105061517 B CN 105061517B
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platinum
platinum complex
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complex crystal
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CN105061517A (en
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罗梅
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Hefei Xiangchen Chemical Engineering Co Ltd
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    • 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
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
    • C07F15/0086—Platinum compounds
    • C07F15/0093—Platinum compounds without a metal-carbon linkage
    • 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

Abstract

A kind of chiral platinum complex crystal, its chemical formula are as follows：

Description

A kind of preparation of chiral platinum complex crystal and synthetic method
First, technical field
The present invention relates to a kind of noval chemical compound and preparation method thereof, more particularly to a kind of chiral coordination compound and its preparation side Method, it is exactly preparation and the synthetic method of a kind of chiral S- benzene glycinol platinum complex.
2nd, background technology
Chiral amino alcohol platinum complex is important catalyst and medication chemistry product, and metal platinum complex is because it is in anticancer The extensive concern of people, the conjunction of metal platinum complex are caused with the potential using value of molecular magnet, fluorescent material etc. There are many document reports in recent years into method.【1-7】
Bibliography：
1.Metal complex catalysis in the synthesis of quinolines, Khusnutdinov, Ravil I.; Bayguzina, Alfiya R.; Dzhemilev, Usein M. Journal of Organometallic Chemistry (2014), 768, 75-114.
2. Derivatisation of an Anti-​Cancer Cationic Antimicrobial Peptide and its Complexation to Platinum(II)
Parker, James P.; Devocelle, Marc; Marmion, Celine J. Zeitschrift fuer Anorganische und Allgemeine Chemie (2013), 639(8-9), 1628-1635.
3. Direct Use of Allylic Alcohols for Platinum-​Catalyzed Monoallylation of Amines Utsunomiya, Masaru; Miyamoto, Yoshiki; Ipposhi, Junji; Ohshima, Takashi; Mashima, Kazushi Organic Letters (2007), 9(17), 3371-3374.
Bis(2-​amino alcohol-​κN)​dicarboxylatoplatinum(II) complexes - elegant synthesis via ring-​opening of bis(2-​amino alcoholato-​κ2N,​O)​ platinum(II) species with dicarboxylic acids
Quick View Other Sources Meelich, Kristof; Galanski, Markus; Arion, Vladimir B.; Keppler, Bernhard K. European Journal of Inorganic Chemistry (2006), (12), 2476-2483.
4. NMR and crystallographic determination of stereoselectivity in the coordination of prochiral olefinic alcohols in mixed olefin-​amino acid Complexes of platinum (II), Erickson, Luther E.; Jones, Garth S.; Blanchard, Jason L.; Ahmed, Kazi J. Inorganic Chemistry (1991), 30(16), 3147-55.
5. Nitrogen-​15 and platinum-​195 nuclear magnetic resonance spectroscopy of platinum complexes. Schiff's base complexes of the tridentate ligand formed from ethanolamine-​15N and salicylaldehyde, Motschi, H.; Pregosin, P. S. Inorganica Chimica Acta (1980), 40(2), 141-6。
3rd, the content of the invention
The present invention is intended to provide the hydration of chirality one two [（S）- benzene glycinol] chlorination platinum complex.Technology to be solved is asked Topic is that one-step synthesis obtains target product.
Chiral coordination compound alleged by the present invention be as platinum tetrachloride and D- benzene glycinol prepare as shown in below formula Compound：
（I）
Chemical name：One hydration two [（S）- benzene glycinol] chlorination platinum complex, abbreviation complex (I).The complex exists Benzaldehyde
Certain catalytic performance is shown in nitrile silicification reaction and Henle reaction, its conversion ratio respectively up to 17.0%, 80.9%。
This synthetic method includes synthesis and separation, described synthesis platinum tetrachloride 1.1101g, D- benzene glycinol 1.3905g, and 30mLTHF make solvent, and back flow reaction prepares saturated solution after 48 hours, with ethanol and chloroform, volatilizees naturally Faint yellow monocrystalline.
Synthetic reaction is as follows：
The step of this synthetic method one obtains target product, and technique is simple, easy to operate.
It is being 3 according to mol ratio that the reaction mechanism of the reaction, which can be speculated as D- benzene glycinol,:The effect of 1 platinum tetrachloride Under, configuration is overturn, and L-type is converted into by D types, a hydrogen atom in amino alcohol on hydroxyl and one in platinum tetrachloride Individual chlorine atom sloughs 1 molecule hydrogen chloride, obtain platinum complex monocrystalline.
Obtain platinum complex monocrystalline.
4th, illustrate
Fig. 1 be a hydration two [（S）- benzene glycinol] chlorination platinum complex X- diffraction analysis figures.
5th, embodiment
1. one hydration two [（S）- benzene glycinol] chlorination platinum complex preparation
In 100mL two-mouth bottles, anhydrous PtCl is added4 1.1101g, 30mL tetrahydrofuran, D- benzene glycinol 1.3905g, Mixture is flowed back 48h, stops reaction, prepares saturated solution with ethanol and chloroform, volatilize to obtain monocrystalline naturally, yield 72%; [a]5 D=-26.0 º (c = 0.0192, CH3OH)：IR (KBr):3386,3243,2962,1586,1511,1467, 1393, 1373, 1262, 1197, 1130, 1049, 588, 529;Elemental analysis data：Calculated value：32.42%, 3.91%, N, 4.73%；Test value：C: 32.50%, H:3.78%, N: 4.58%;
Match crystal volume data is as follows：
Empirical formula C16H23Cl3N2O3 Pt
Molecular weight 592.80
Temperature 293 (2) K
Wavelength 0.71073
Crystallographic system, Space group Monoclinic system, P2 (1)
Cell parameter a=6.543 (5) α=90 °
b = 11.919(11) Å β = 98.240 °.
c = 13.554(9) Å γ = 90 °.
Volume 1046.2（12）Å^3
The Mg/m^3 of charge density 2,1.882
The mm^-1 of absorption correction parameter 7.106
Number of electrons 5289 in unit cell
The x 0.090x 0.040mm of crystal size 0.120
The to 25.487 of scope 2.286 at Theta angles
HKL index capture range -7<=h<=7, -10<k<14, -16<l<=14
Collection/independent diffraction data 2831/ 112/202 [R (int)=0.1058]
The % of data integrity degree 99.7 of theta=30.5
The method Multi Slice Mode of absorption correction
The and 0.4848 of transmitance 0.7456 of minimax
The Matrix least square method for the method F^2 that refine uses
Number/number of parameters 4615/36/290 of data number/use limitation
The method 1.034 that refine uses
The uniformity factor R 1=0.0656 of point diffraction, ω R2=0.1425
The identical factor R 1=0.0993 of observable diffraction, ω R2=0.1576
Absolute configuration parameter 0.19（3）
And -1.086e. the ^-3 of maximum summit and peak valley 2.482 on difference Fourier figure
The typical bond distance's data of crystal：
Pt(1)-O(1) 2.05(2)
Pt(1)-N(2) 2.05(3)
Pt(1)-N(1) 2.06(3)
Pt(1)-Cl(3) 2.323(7)
Pt(1)-Cl(1) 2.330(8)
Pt(1)-Cl(2) 2.329(7)
N(1)-C(2) 1.37(5)
N(1)-H(1A) 0.9700
N(1)-H(1B) 0.9700
N(2)-C(10) 1.57(5)
N(2)-H(2A) 0.9700
N(2)-H(2B) 0.9700
O(1)-C(1) 1.35(4)
O(2)-C(9) 1.40(3)
O(2)-H(2) 0.8200
O(3)-H(3B) 0.8908
O(3)-H(3A) 0.8085
C(1)-C(2) 1.64(6)
C(1)-H(1C) 0.9700
C(1)-H(1D) 0.9700
C(2)-C(3) 1.53(5)
C(2)-H(2C) 0.9800
C(3)-C(4) 1.3900
C(3)-C(8) 1.3900
C(4)-C(5) 1.3900
C(4)-H(4) 0.9300
C(5)-C(6) 1.3900
C(5)-H(5) 0.9300
C(6)-C(7) 1.3900
C(6)-H(6) 0.9300
C(7)-C(8) 1.3900
C(7)-H(7) 0.9300
C(8)-H(8) 0.9300
C(9)-C(10) 1.59(5)
C(9)-H(9A) 0.9700
C(9)-H(9B) 0.9700
C(10)-C(11) 1.45(4)
C(10)-H(10) 0.9800
C(11)-C(12) 1.3900
C(11)-C(16) 1.3900
C(12)-C(13) 1.3900
C(12)-H(12) 0.9300
C(13)-C(14) 1.3900
C(13)-H(13) 0.9300
C(14)-C(15) 1.3900
C(14)-H(14) 0.9300
C(15)-C(16) 1.3900
C(15)-H(15) 0.9300
C(16)-H(16) 0.9300
The typical bond angle data of crystal：
O(1)-Pt(1)-N(2) 175.0(12)
O(1)-Pt(1)-N(1) 81.6(10)
N(2)-Pt(1)-N(1) 96.8(9)
O(1)-Pt(1)-Cl(3) 89.1(7)
N(2)-Pt(1)-Cl(3) 86.2(9)
N(1)-Pt(1)-Cl(3) 87.6(8)
O(1)-Pt(1)-Cl(1) 87.6(6)
N(2)-Pt(1)-Cl(1) 93.8(10)
N(1)-Pt(1)-Cl(1) 168.9(8)
Cl(3)-Pt(1)-Cl(1) 90.0(3)
O(1)-Pt(1)-Cl(2) 91.0(7)
N(2)-Pt(1)-Cl(2) 93.6(9)
N(1)-Pt(1)-Cl(2) 90.8(8)
Cl(3)-Pt(1)-Cl(2) 178.3(3)
Cl(1)-Pt(1)-Cl(2) 91.7(3)
C(2)-N(1)-Pt(1) 118(3)
C(2)-N(1)-H(1A) 107.9
Pt(1)-N(1)-H(1A) 107.9
C(2)-N(1)-H(1B) 107.9
Pt(1)-N(1)-H(1B) 107.9
H(1A)-N(1)-H(1B) 107.2
C(10)-N(2)-Pt(1) 122(2)
C(10)-N(2)-H(2A) 106.9
Pt(1)-N(2)-H(2A) 106.9
C(10)-N(2)-H(2B) 106.9
Pt(1)-N(2)-H(2B) 106.9
H(2A)-N(2)-H(2B) 106.7
C(1)-O(1)-Pt(1) 106(2)
C(9)-O(2)-H(2) 109.5
H(3B)-O(3)-H(3A) 170.1
O(1)-C(1)-C(2) 116(3)
O(1)-C(1)-H(1C) 108.3
C(2)-C(1)-H(1C) 108.3
O(1)-C(1)-H(1D) 108.3
C(2)-C(1)-H(1D) 108.3
H(1C)-C(1)-H(1D) 107.4
N(1)-C(2)-C(3) 106(3)
N(1)-C(2)-C(1) 102(3)
C(3)-C(2)-C(1) 120(3)
N(1)-C(2)-H(2C) 109.1
C(3)-C(2)-H(2C) 109.1
C(1)-C(2)-H(2C) 109.1
C(4)-C(3)-C(8) 120.0
C(4)-C(3)-C(2) 125(2)
C(8)-C(3)-C(2) 114(2)
C(3)-C(4)-C(5) 120.0
C(3)-C(4)-H(4) 120.0
C(5)-C(4)-H(4) 120.0
C(6)-C(5)-C(4) 120.0
C(6)-C(5)-H(5) 120.0
C(4)-C(5)-H(5) 120.0
C(5)-C(6)-C(7) 120.0
C(5)-C(6)-H(6) 120.0
C(7)-C(6)-H(6) 120.0
C(8)-C(7)-C(6) 120.0
C(8)-C(7)-H(7) 120.0
C(6)-C(7)-H(7) 120.0
C(7)-C(8)-C(3) 120.0
C(7)-C(8)-H(8) 120.0
C(3)-C(8)-H(8) 120.0
O(2)-C(9)-C(10) 115(3)
O(2)-C(9)-H(9A) 108.4
C(10)-C(9)-H(9A) 108.4
O(2)-C(9)-H(9B) 108.4
C(10)-C(9)-H(9B) 108.4
H(9A)-C(9)-H(9B) 107.5
C(11)-C(10)-N(2) 117(3)
C(11)-C(10)-C(9) 108(3)
N(2)-C(10)-C(9) 105(3)
C(11)-C(10)-H(10) 108.6
N(2)-C(10)-H(10) 108.6
C(9)-C(10)-H(10) 108.6
C(12)-C(11)-C(16) 120.0
C(12)-C(11)-C(10) 117(2)
C(16)-C(11)-C(10) 123(2)
C(11)-C(12)-C(13) 120.0
C(11)-C(12)-H(12) 120.0
C(13)-C(12)-H(12) 120.0
C(12)-C(13)-C(14) 120.0
C(12)-C(13)-H(13) 120.0
C(14)-C(13)-H(13) 120.0
C(15)-C(14)-C(13) 120.0
C(15)-C(14)-H(14) 120.0
C(13)-C(14)-H(14) 120.0
C(16)-C(15)-C(14) 120.0
C(16)-C(15)-H(15) 120.0
C(14)-C(15)-H(15) 120.0
C(15)-C(16)-C(11) 120.0
C(15)-C(16)-H(16) 120.0
C(11)-C(16)-H(16) 120.0
2. nitrile silicification reaction application
2- phenyl -2-（Three silyloxies）Propionitrile
The ml (3.3mmol) of 0.2mmol complex I, benzaldehyde 0.1mL, TMSCN 0.3,2mL absolute methanols, Added in succession under 30 ~ 35 C, after 40 hours, add water quenching and go out after post layer（Petroleum ether/dichloromethane：5/1）, obtain colourless Oily liquids, conversion ratio：17.0 %;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)。
3. Henle reaction application
Take 0.20mmol complex I（Catalytic amount is 20%）In 25mL small flask, add 2 milliliters without water beetle Alcoholic solution, then, 0.1mL benzaldehyde and 0.5mL nitromethane are added into above-mentioned solution, is stirred at room temperature, reaction 40 is small Shi Hou, carry out nmr analysis, conversion ratio：80.9 %；1H NMR (300MHz, CDCl3) 7.28~7.32 (m, 5H, Ar- ), H 5.32~5.35 (d, J=9.18Hz, 1H ,-CH), 4.38~4.56 (m, 2H ,-CH2), 3.89 (br, 1H, -OH)。
4. allyl group alkylated reaction application
Take 0.10mmol complex I（Catalytic amount is 20%）In 25mL small flask, 2 milliliters of dichloromethane is added Alkane solution, then, addition 0.1mL benzaldehyde and 0.3mL allyl trimethyl silane into above-mentioned solution, stirring at normal temperature, After reaction 40 hours, nmr analysis, conversion ratio are carried out：53%；1H NMR (300MHz, CDCl3) 7.27~7.33 (m, 5H, ), Ar-H 5.79~5.80 (m, 1H), 5.12~5.17 (m, 2H ,-CH2), 4.71（D, J=5Hz, 1H）, 2.49~ 2.50 (m, 2H), 2.28（s, 1H）.

Claims (2)

1. a kind of chiral platinum complex crystal for having following cell parameter, at a temperature of 293 (2) K, in Oxford, X-ray monocrystalline spreads out Penetrate on instrument, with the MoK alpha rays through graphite monochromator monochromatizationDiffraction data is collected with ω-θ scan modes, its It is characterised by crystal category orthorhombic system, space group P2 (1), cell parameter：α=90 °；β =98.240 °；γ=90 °, it is characterised in that：It is being prepared by platinum tetrachloride and D- benzene glycinol, by following Complex shown in chemical formula (I)：
2. the synthetic method of the chiral platinum complex crystal (I) described in claim 1, including synthesize and separate, described synthesis Make solvent with platinum tetrachloride 1.1101g, D- benzene glycinol 1.3905g, and 30mLTHF, back flow reaction is after 48 hours, with ethanol and Chloroform prepares saturated solution, and volatilize to obtain faint yellow monocrystalline naturally.
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CN103467313A (en) * 2013-09-09 2013-12-25 合肥工业大学 Chiral copper complex
CN103588821A (en) * 2013-10-16 2014-02-19 合肥工业大学 Chiral phenylglycinol nickel complex
CN104892644A (en) * 2015-06-18 2015-09-09 合肥祥晨化工有限公司 Synthetic method of chiral D-phenylglycinol copper chloride complex

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Publication number Priority date Publication date Assignee Title
CN103467313A (en) * 2013-09-09 2013-12-25 合肥工业大学 Chiral copper complex
CN103588821A (en) * 2013-10-16 2014-02-19 合肥工业大学 Chiral phenylglycinol nickel complex
CN104892644A (en) * 2015-06-18 2015-09-09 合肥祥晨化工有限公司 Synthetic method of chiral D-phenylglycinol copper chloride complex

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