CN103193808A - Chirality zinc complex - Google Patents
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- CN103193808A CN103193808A CN2013101550875A CN201310155087A CN103193808A CN 103193808 A CN103193808 A CN 103193808A CN 2013101550875 A CN2013101550875 A CN 2013101550875A CN 201310155087 A CN201310155087 A CN 201310155087A CN 103193808 A CN103193808 A CN 103193808A
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- title complex
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- cyanopyridine
- column chromatography
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- 239000011701 zinc Substances 0.000 title claims abstract description 50
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 title claims abstract description 5
- 229910052725 zinc Inorganic materials 0.000 title claims abstract description 5
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims abstract description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000013078 crystal Substances 0.000 claims abstract description 10
- FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical compound N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 238000004440 column chromatography Methods 0.000 claims abstract description 6
- STVVMTBJNDTZBF-VIFPVBQESA-N L-phenylalaninol Chemical compound OC[C@@H](N)CC1=CC=CC=C1 STVVMTBJNDTZBF-VIFPVBQESA-N 0.000 claims abstract description 5
- 239000002904 solvent Substances 0.000 claims abstract description 5
- 239000000126 substance Substances 0.000 claims abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 238000000605 extraction Methods 0.000 claims description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- 238000002447 crystallographic data Methods 0.000 claims description 4
- 238000010189 synthetic method Methods 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 239000003480 eluent Substances 0.000 claims description 2
- 229910002804 graphite Inorganic materials 0.000 claims description 2
- 239000010439 graphite Substances 0.000 claims description 2
- 238000001556 precipitation Methods 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims description 2
- 125000006850 spacer group Chemical group 0.000 claims description 2
- QNRATNLHPGXHMA-XZHTYLCXSA-N (r)-(6-ethoxyquinolin-4-yl)-[(2s,4s,5r)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]methanol;hydrochloride Chemical compound Cl.C([C@H]([C@H](C1)CC)C2)CN1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OCC)C=C21 QNRATNLHPGXHMA-XZHTYLCXSA-N 0.000 claims 1
- 238000006555 catalytic reaction Methods 0.000 abstract description 5
- 238000010992 reflux Methods 0.000 abstract description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 abstract 2
- 238000006842 Henry reaction Methods 0.000 abstract 1
- 238000002955 isolation Methods 0.000 abstract 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 abstract 1
- 239000003208 petroleum Substances 0.000 abstract 1
- 238000001308 synthesis method Methods 0.000 abstract 1
- -1 Acyclic Alkenes Chemical class 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 238000012937 correction Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L Zinc chloride Inorganic materials [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- UHIJLWIHCPPKOP-UHFFFAOYSA-N [N].[Zn] Chemical compound [N].[Zn] UHIJLWIHCPPKOP-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 235000005074 zinc chloride Nutrition 0.000 description 2
- 239000011592 zinc chloride Substances 0.000 description 2
- GBSQTQRZHMQHGH-UHFFFAOYSA-N 2-pyridin-2-yl-4,5-dihydro-1,3-oxazole Chemical compound O1CCN=C1C1=CC=CC=N1 GBSQTQRZHMQHGH-UHFFFAOYSA-N 0.000 description 1
- PZVKSFBOPQYWGM-UHFFFAOYSA-N 4,5-dihydro-1,3-oxazole;pyridine Chemical class C1CN=CO1.C1=CC=NC=C1 PZVKSFBOPQYWGM-UHFFFAOYSA-N 0.000 description 1
- 230000004568 DNA-binding Effects 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
- 238000004458 analytical method Methods 0.000 description 1
- 238000011914 asymmetric synthesis Methods 0.000 description 1
- 238000005564 crystal structure determination Methods 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000011982 enantioselective catalyst Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000006459 hydrosilylation reaction Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229940067107 phenylethyl alcohol Drugs 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
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- Catalysts (AREA)
Abstract
The invention discloses a chirality zinc complex. The chemical formula is as shown in the specification. The synthesis method of the complex comprises refluxing and reacting 2-cyanopyridine and L-phenylalaninol in a chlorobenzene solvent for 60 hours. The complex (I) is sprayed and washed by using petroleum ether and dichloromethane, subjected to column chromatography isolation and naturally volatilizes so as to obtain a complex single crystal. The complex shows good catalysis property in henry reaction of benzaldehyde.
Description
One, technical field
The present invention relates to a kind of metal organic coordination compounds (title complex) and preparation method thereof, particularly nitrogenous chiral metal organic coordination compound and preparation method thereof exactly is a kind of chiral zinc nitrogen complex and synthetic method thereof.
Two, background technology
Along with vitochemical development, the application of organometallics in organic synthesis is more and more wide, is one of field very active in the present organic chemistry, is widely used in the organic synthesis.The use chiral ligand that the later stage sixties 20th century occurs and the asymmetric catalysis synthesis of transition metal complex catalysis have accelerated the research of chiral drug greatly.The important content of chemical catalysis asymmetric synthesis method is chiral ligand and containing metal catalyst design, thereby makes reaction have efficient and high enantioselectivity.Usually the used part Shi oxazoline of asymmetric catalyst, Jin Lai oxazoline Zn complex are extensively synthesized and are obtained catalytic effect preferably.
·
Reference:
1.
Enantioselective diene cyclization/hydrosilylation catalyzed by optically active palladium bisoxazoline and pyridine-oxazoline complexes ， Perch, Nicholas S.; Pei, Tao; Widenhoefer, Ross A. Journal of Organic Chemistry (2000), 65(12), 3836-3845.
2.
Synthesis and evaluation of the in vitro DNA-binding properties of chiral cis-dichloro(pyridyloxazoline)platinum(II) complexes , Dodd, David W.; Toews, Heather E.; Trevail, Michael J.; Jennings, Michael C.; Hudson, Robert H. E.; Jones, Nathan D., Canadian Journal of Chemistry (2009), 87(1), 321-327.
3.
Asymmetric Intermolecular Heck-Type Reaction of Acyclic Alkenes via Oxidative Palladium(II) Catalysis ,Yoo, Kyung Soo; Park, Chan Pil; Yoon, Cheol Hwan; Sakaguchi, Satoshi; O'Neill, Justin; Jung, Kyung Woon, Organic Letters (2007), 9(20), 3933-3935。
Three, summary of the invention
The present invention aims to provide a kind of Zn-N a metal-organic complex to be applied to catalytic field, and technical problem Lin Xuan oxazoline to be solved is as part and synthesis of chiral zinc-nitrogen coordination compound.
The alleged chiral zinc title complex of the present invention is 2-[4 (S)-benzyl-4,5-dihydro] oxazolinyl pyridine Zn complex by the preparation of adjacent cyanopyridine by the title complex shown in the following chemical formula:
Chemical name: two { 2-[4 (S)-benzyl-4,5-dihydro] oxazolinyl pyridine } zinc chloride title complex, be called for short title complex (I).
The synthetic method of this title complex (I) comprises reaction, separation and purifying, it is characterized in that by 2-cyanopyridine 2.0g and L-phenylalaninol 3.4g under the anhydrous and oxygen-free condition and the anhydrous ZnCl of catalyzer
2In the time of (115mol%) in chlorobenzene solvent back flow reaction 60 hours separate, purifying, i.e. reaction is sloughed chlorobenzene after finishing, chloroform extraction is used in the back that is dissolved in water, and uses column chromatography purification behind the extraction phase precipitation; The synthetic method of this title complex (I) is 2-cyanopyridine and L-phenylalaninol back flow reaction 60 hours in chlorobenzene solvent.Title complex (I) is with sherwood oil and eluent methylene chloride, column chromatography for separation, volatilize naturally complex monocrystal.This title complex has shown catalytic performance preferably in the Henle reaction of phenyl aldehyde, its transformation efficiency reaches 77.8%.
Four, description of drawings
Fig. 1 is the single crystal diffraction figure of title complex (I).
Five, embodiment
(1) preparation of two { 2-[4 (S)-benzyl-4,5-dihydro] oxazolinyl pyridine } zinc chloride title complex
In the 100mL two-mouth bottle, under the anhydrous and oxygen-free condition, add anhydrous ZnCl
23.0 g (22.06mmol), the 40mL chlorobenzene, 2-cyanopyridine 2.0g (19.23mmol), L-phenylalaninol 3.9929g, with the mixture 60h that at high temperature refluxes, stopped reaction, decompression is with desolventizing,, with the residuum water dissolution, and use CHCl
3(20mLx2) extraction, the organic phase anhydrous sodium sulfate drying, the rotation desolventizing with sherwood oil/methylene dichloride (1:9) column chromatography, gets white crystal, M.P.:16-162 ° of C, productive rate: 85% with thick product; [a]
5 D=+72.7o (c=0.062, CH
3OH):,
1HNMR (600MHz, CDCl
3) 8.78 (s, 2H), 8.18(s, 2H), 8.04～8.05 (m, 2H, Ar-H), 7.83 (s, 2H), 7.41～7.43 (m, 1H, Ar-H), 7.21～7.30 (m, 9H, Ar-H), 4.71～4.74 (m, 2H), 4.64 (m, 2H), 4.50 (s, 2H), 3.12～3.14 (m, 2H), 2.80～2.84 (m, 2H);
13CNMR 65.5 (x2), 74.9 (x2),
124.2 (x2), 127.0(x2), 127.5 (x4), 128.9 (x8), 130.7 (x2), 137.4 (x2), 149.8(x4), 164.7 (x2); IR: 3447,3057,1654,1590,1494,1443,1403,1299,1251,1152,1087,1017,935,806,748,705,684,635; Ultimate analysis: C:48.20 %, H:3.76 %, N:7.45 %.
The crystal structure determination of compound:
The monocrystalline of choosing suitable size at microscopically at room temperature carries out the experiment of X-ray single crystal diffraction, under the 293k temperature, on Oxford X-ray single crystal diffractometer, use through the MoKa of graphite monochromator monochromatization ray (λ=0.71073 A) and collect diffraction data with the w-Theta scan mode.The gained data are carried out the Lp factor and experience absorption correction, and crystalline structure is solved by direct method, and diffraction data reduction and structure elucidation work use SAINT-5.0 and SHELXS-97 program to finish respectively.Crystal data is as follows:
Empirical formula C30H28 Cl4 N4 O2 Zn2
Molecular weight 749.10
Temperature 293 (2) K
Wavelength 0.71073 A
Crystallographic system, spacer triclinic(crystalline)system, P (1)
Unit cell parameters a=8.992 (3) A alpha=76.582 (5) deg.
b = 9.043(2) A beta = 69.781(5) deg.
c = 11.712(3) A gamma = 63.163(5) deg.
Volume 794.2(4) A^3
Electric density 1,1.566 Mg/m^3
Absorption correction parameter 1.881 mm^-1
Number of electrons 380 in the unit cell
Crystallographic dimension 0.2034x 0.175x 0.121 mm
Scope 1.86 to 26.00 at Theta angle
Index capture range-10＜=h＜=11 of HKL ,-11＜=k＜11 ,-14＜=l＜=13
Collection/independent diffraction data 4705/ 3808 [R (int)=0.0428]
Data integrity degree 98.6 % of theta=30.5
The method Multi Slice Mode of absorption correction
Transmitance 1.0000 and 0.40176 of minimax
The matrix method of least squares of the method F^2 that refine is used
Number/the number of parameters 3808/3/380 of data number/use restriction
The method 1.029 that refine is used
The consistence factor R 1=0.0555 of point diffraction, wR2=0.1422
Can observe the identical factor R 1=0.0600 of diffraction, wR2=0.1462
Absolute configuration parameter 0.00(2)
Maximum summit on the difference Fourier figure and peak valley 1 .019 and-1.046 e.A^-3
The typical bond distance's data of crystal:
Zn(1)-N(2) 2.064(7)
Zn(1)-Cl(1) 2.231(2)
Zn(1)-N(1) 2.240(7)
Zn(1)-Cl(3) 2.285(3)
Zn(1)-Cl(4) 2.653(2)
Zn(2)-N(4) 2.049(7)
Zn(2)-Cl(2) 2.227(2)
Zn(2)-N(3) 2.241(8)
Zn(2)-Cl(4) 2.284(2)
Zn(2)-Cl(3) 2.608(3)
N(1)-C(1) 1.308(11)
N(1)-C(5) 1.311(10)
N(2)-C(6) 1.290(11)
N(2)-C(8) 1.481(10)
N(3)-C(16) 1.341(12)
N(3)-C(20) 1.344(10)
N(4)-C(21) 1.263(11)
N(4)-C(23) 1.486(10)
O(1)-C(6) 1.317(9)
O(1)-C(7) 1.465(10)
O(2)-C(21) 1.346(9)
O(2)-C(22) 1.443(11)
The bond angle data of crystal
N(2)-Zn(1)-Cl(1) 116.0(2)
N(2)-Zn(1)-N(1) 76.7(3)
Cl(1)-Zn(1)-N(1) 102.8(2)
N(2)-Zn(1)-Cl(3) 131.0(2)
Cl(1)-Zn(1)-Cl(3) 112.93(10)
N(1)-Zn(1)-Cl(3) 90.75(19)
N(2)-Zn(1)-Cl(4) 89.5(2)
Cl(1)-Zn(1)-Cl(4) 99.04(8)
N(1)-Zn(1)-Cl(4) 157.61(18)
Cl(3)-Zn(1)-Cl(4) 85.06(8)
N(4)-Zn(2)-Cl(2) 118.1(2)
N(4)-Zn(2)-N(3) 76.0(3)
Cl(2)-Zn(2)-N(3) 99.4(2)
N(4)-Zn(2)-Cl(4) 126.0(2)
Cl(2)-Zn(2)-Cl(4) 115.95(9)
N(3)-Zn(2)-Cl(4) 94.27(19)
N(4)-Zn(2)-Cl(3) 87.7(2)
Cl(2)-Zn(2)-Cl(3) 98.24(10)
N(3)-Zn(2)-Cl(3) 160.09(18)
Cl(4)-Zn(2)-Cl(3) 86.14(8)
Zn(1)-Cl(3)-Zn(2) 94.99(8)
Zn(2)-Cl(4)-Zn(1) 93.79(7)
C(1)-N(1)-C(5) 119.7(8)
C(1)-N(1)-Zn(1) 128.5(6)
C(5)-N(1)-Zn(1) 111.8(5)
C(6)-N(2)-C(8) 107.5(7)
C(6)-N(2)-Zn(1) 114.8(6)
C(8)-N(2)-Zn(1) 137.3(6)
C(16)-N(3)-C(20) 117.3(8)
C(16)-N(3)-Zn(2) 130.0(6)
C(20)-N(3)-Zn(2) 112.7(6)
C(21)-N(4)-C(23) 107.8(6)
C(21)-N(4)-Zn(2) 116.7(5)
C(23)-N(4)-Zn(2) 135.6(5)
C(6)-O(1)-C(7) 106.4(6)
C(21)-O(2)-C(22) 105.6(6)
N(1)-C(1)-C(2) 121.5(8)
N(1)-C(1)-H(1) 119.2
O(4)-Zn(1)-N(2) 165.8(2) 。
(2), Henle reaction is used
1.
The preparation of 2-nitro 1-phenylethyl alcohol
Catalyst I (0.15mmol), phenyl aldehyde 0.10 mL (0.986 mmol) and Nitromethane 99Min. (0.50 mL, 9.255 mmol) at room temperature stir 48 h, and productive rate is: 77.8 %%,
1H NMR (300MHz, CDCl
3) 7.28～7.32 (m, 5H, Ar-H), 5.32～5.35 (d, J=9.18Hz, 1H ,-CH), 4.38～4.56 (m, 2H ,-CH
2), 3.89 (br, 1H ,-OH).
13C NMR (75 MHz, CDCl
3) 138.30 128.92 (x2), 128.82,125.98 (x2), 81.16,70.9.
[0010]
Claims (2)
1. chiral zinc title complex is characterized in that: by adjacent cyanopyridine and L-phenylalaninol under the anhydrous and oxygen-free condition and the anhydrous ZnCl of catalyzer
2When (115 mol%) in chlorobenzene solvent back flow reaction 60 hours, by the title complex shown in the following chemical formula (I):
（I）。
2. the described title complex of claim 1 (I), under the 293k temperature, on Oxford X-ray single crystal diffractometer, with collecting diffraction data through the MoKa of graphite monochromator monochromatization ray (λ=0.71073 A) with the w-Theta scan mode, it is characterized in that crystal belongs to rhombic system, spacer C 2, unit cell parameters: a=8.992 (3) A alpha=76.582 (5) deg;
b = 9.043(2) A beta = 69.781(5) deg； c = 11.712(3) A gamma = 63.163(5) deg.
The synthetic method of the described title complex of claim 1 (I), by 2-cyanopyridine and L-phenylamino alcohol under the anhydrous and oxygen-free condition and the anhydrous ZnCl of catalyzer
2When (126 mol%) in chlorobenzene solvent back flow reaction 60 hours separate, purifying, i.e. reaction is sloughed chlorobenzene after finishing, chloroform extraction is used in the back that is dissolved in water, and uses column chromatography purification behind the extraction phase precipitation; Title complex (I) is with sherwood oil and eluent methylene chloride, column chromatography for separation, volatilize naturally complex monocrystal.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103333104A (en) * | 2013-07-30 | 2013-10-02 | 罗梅 | Preparation and synthesis method of 2-benzamides pyridinium acetate |
| CN105218473A (en) * | 2015-10-18 | 2016-01-06 | 合肥祥晨化工有限公司 | A kind of chiral zinc nitrogen complexes containing methanol crystallization |
| CN106432293A (en) * | 2016-10-05 | 2017-02-22 | 合肥祥晨化工有限公司 | Chiral zinc complex |
| CN106496254A (en) * | 2016-10-18 | 2017-03-15 | 合肥祥晨化工有限公司 | A kind of chiral zinc nitrogen complexes |
| CN106632426B (en) * | 2016-10-01 | 2018-04-20 | 合肥祥晨化工有限公司 | A kind of chiral zinc nitrogen complexes |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102690279A (en) * | 2012-06-06 | 2012-09-26 | 罗梅 | Chiral zinc complex |
-
2013
- 2013-04-29 CN CN201310155087.5A patent/CN103193808B/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102690279A (en) * | 2012-06-06 | 2012-09-26 | 罗梅 | Chiral zinc complex |
Non-Patent Citations (3)
| Title |
|---|
| DODD, DAVID等: "Synthesis and evaluation of the in vitro DNA-binding properties of chiral cis-dichloro(pyridyloxazoline)platinum(II) complexes", 《CANADIAN JOURNAL OF CHEMISTRY》 * |
| KYUNG SOO YOO等: "Asymmetric Intermolecular Heck-Type Reaction of Acyclic Alkenes via Oxidative Palladium(II) Catalysis", 《ORGANIC LETTERS》 * |
| NICHOLAS S. PERCH等: "Enantioselective Diene Cyclization/Hydrosilylation Catalyzed by Optically Active Palladium Bisoxazoline and Pyridine Oxazoline Complexes", 《JOURNAL OF ORGANIC CHEMISTRY》 * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103333104A (en) * | 2013-07-30 | 2013-10-02 | 罗梅 | Preparation and synthesis method of 2-benzamides pyridinium acetate |
| CN105218473A (en) * | 2015-10-18 | 2016-01-06 | 合肥祥晨化工有限公司 | A kind of chiral zinc nitrogen complexes containing methanol crystallization |
| CN106632426B (en) * | 2016-10-01 | 2018-04-20 | 合肥祥晨化工有限公司 | A kind of chiral zinc nitrogen complexes |
| CN106432293A (en) * | 2016-10-05 | 2017-02-22 | 合肥祥晨化工有限公司 | Chiral zinc complex |
| CN106496254A (en) * | 2016-10-18 | 2017-03-15 | 合肥祥晨化工有限公司 | A kind of chiral zinc nitrogen complexes |
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