CN106008611A - Chiral cobalt complex - Google Patents
Chiral cobalt complex Download PDFInfo
- Publication number
- CN106008611A CN106008611A CN201610386011.7A CN201610386011A CN106008611A CN 106008611 A CN106008611 A CN 106008611A CN 201610386011 A CN201610386011 A CN 201610386011A CN 106008611 A CN106008611 A CN 106008611A
- Authority
- CN
- China
- Prior art keywords
- complex
- cobalt
- phenylalaninol
- cobalt complex
- chiral
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000004700 cobalt complex Chemical class 0.000 title claims abstract description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000013078 crystal Substances 0.000 claims abstract description 9
- STVVMTBJNDTZBF-SECBINFHSA-N (2r)-2-amino-3-phenylpropan-1-ol Chemical compound OC[C@H](N)CC1=CC=CC=C1 STVVMTBJNDTZBF-SECBINFHSA-N 0.000 claims abstract description 5
- 238000010992 reflux Methods 0.000 claims abstract description 4
- 238000003756 stirring Methods 0.000 claims abstract description 4
- 239000000126 substance Substances 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 8
- 230000015572 biosynthetic process Effects 0.000 claims description 7
- 238000003786 synthesis reaction Methods 0.000 claims description 7
- 238000010189 synthetic method Methods 0.000 claims description 5
- 244000061458 Solanum melongena Species 0.000 claims description 3
- GDUDPOLSCZNKMK-UHFFFAOYSA-L cobalt(2+);diacetate;hydrate Chemical compound O.[Co+2].CC([O-])=O.CC([O-])=O GDUDPOLSCZNKMK-UHFFFAOYSA-L 0.000 claims description 3
- 238000002447 crystallographic data Methods 0.000 claims description 2
- 230000005260 alpha ray Effects 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 239000004575 stone Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 8
- 230000003197 catalytic effect Effects 0.000 abstract description 3
- 238000006842 Henry reaction Methods 0.000 abstract 1
- BULOCEWDRJUMEL-UHFFFAOYSA-N benzene formaldehyde Chemical compound C=O.C1=CC=CC=C1.C=O BULOCEWDRJUMEL-UHFFFAOYSA-N 0.000 abstract 1
- ZBYYWKJVSFHYJL-UHFFFAOYSA-L cobalt(2+);diacetate;tetrahydrate Chemical compound O.O.O.O.[Co+2].CC([O-])=O.CC([O-])=O ZBYYWKJVSFHYJL-UHFFFAOYSA-L 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 238000001308 synthesis method Methods 0.000 abstract 1
- SWGJCIMEBVHMTA-UHFFFAOYSA-K trisodium;6-oxido-4-sulfo-5-[(4-sulfonatonaphthalen-1-yl)diazenyl]naphthalene-2-sulfonate Chemical compound [Na+].[Na+].[Na+].C1=CC=C2C(N=NC3=C4C(=CC(=CC4=CC=C3O)S([O-])(=O)=O)S([O-])(=O)=O)=CC=C(S([O-])(=O)=O)C2=C1 SWGJCIMEBVHMTA-UHFFFAOYSA-K 0.000 abstract 1
- 238000005303 weighing Methods 0.000 abstract 1
- -1 D-phenylalaninol cobalt Chemical compound 0.000 description 7
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 6
- 150000001414 amino alcohols Chemical class 0.000 description 5
- 238000000034 method Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 3
- JAWGVVJVYSANRY-UHFFFAOYSA-N cobalt(3+) Chemical class [Co+3] JAWGVVJVYSANRY-UHFFFAOYSA-N 0.000 description 3
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 235000013495 cobalt Nutrition 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- XUEWIQNQPBSCOR-UHFFFAOYSA-N 2-nitro-1-phenylethanol Chemical compound [O-][N+](=O)CC(O)C1=CC=CC=C1 XUEWIQNQPBSCOR-UHFFFAOYSA-N 0.000 description 1
- 102000004316 Oxidoreductases Human genes 0.000 description 1
- 108090000854 Oxidoreductases Proteins 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 1
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 description 1
- 238000009876 asymmetric hydrogenation reaction Methods 0.000 description 1
- 150000001868 cobalt Chemical class 0.000 description 1
- GSOLWAFGMNOBSY-UHFFFAOYSA-N cobalt Chemical compound [Co][Co][Co][Co][Co][Co][Co][Co] GSOLWAFGMNOBSY-UHFFFAOYSA-N 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 150000001869 cobalt compounds Chemical class 0.000 description 1
- LBFUKZWYPLNNJC-UHFFFAOYSA-N cobalt(ii,iii) oxide Chemical compound [Co]=O.O=[Co]O[Co]=O LBFUKZWYPLNNJC-UHFFFAOYSA-N 0.000 description 1
- HQWPLXHWEZZGKY-UHFFFAOYSA-N diethylzinc Chemical compound CC[Zn]CC HQWPLXHWEZZGKY-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 230000005311 nuclear magnetism Effects 0.000 description 1
- 238000004611 spectroscopical analysis Methods 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
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/06—Cobalt compounds
- C07F15/065—Cobalt compounds without a metal-carbon linkage
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
- B01J31/2208—Oxygen, e.g. acetylacetonates
- B01J31/2217—At least one oxygen and one nitrogen atom present as complexing atoms in an at least bidentate or bridging ligand
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
- B01J2231/42—Catalytic cross-coupling, i.e. connection of previously not connected C-atoms or C- and X-atoms without rearrangement
- B01J2231/4205—C-C cross-coupling, e.g. metal catalyzed or Friedel-Crafts type
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
- B01J2531/0202—Polynuclearity
- B01J2531/0211—Metal clusters, i.e. complexes comprising 3 to about 1000 metal atoms with metal-metal bonds to provide one or more all-metal (M)n rings, e.g. Rh4(CO)12
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
- B01J2531/0238—Complexes comprising multidentate ligands, i.e. more than 2 ionic or coordinative bonds from the central metal to the ligand, the latter having at least two donor atoms, e.g. N, O, S, P
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/84—Metals of the iron group
- B01J2531/845—Cobalt
-
- 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)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A chiral cobalt complex (I) has a chemical formula as follows. A synthesis method of the complex (I) is as below: weighing 4.3811g (0.03mol) of D-phenylalaninol and 2.4217g (0.01mol) of cobaltous acetate tetrahydrate, adding into a 100mL round bottom flask, adding 30ml of anhydrous methanol, stirring for dissolving, and conducting heating reflux for 48h; after the reaction, filtering while hot, naturally volatilizing to precipitate a purple red crystal a few days later. The complex in a Henry reaction of benzene formaldehyde shows a good catalytic performance, and reaches the conversion rate of 99%.
Description
Technical field
The present invention relates to a kind of noval chemical compound and preparation method thereof, particularly to a kind of cobalt compound and preparation method thereof,
It is exactly preparation and the synthetic method of a kind of chiral D-phenylalaninol cobalt complex.
Background technology
Chiral amino alcohol cobalt complex is important catalyst and medication chemistry product, its as catalyst at diethyl zinc
Preferable catalytic effect is had in reacting with benzaldehyde enantioselective addition etc..【1-5】
List of references:
1.Asymmetric hydrogenation catalyzed by bis(dimethylglyoximato)cobalt
(II)-achiral base complex and chiral amino alcohol conjugated
Systems.Oxidoreductase model with enantioselectivity, Ohgo, Yoshiaki; Natori,
Yukikazu; Takeuchi, Seiji; Yoshimura, Juji , Chemistry Letters (1974), (11),
1327-30.
Synthesis, structure and acid-base properties of cobalt(III) complexes
with aminoalcohols tepanenko, O. N.; Reiter, 2. L. G. Ukrainskii Khimicheskii
Zhurnal (Russian Edition), (1992), 58(12), 1047-54.
3. Cobalt(III) mono- and trinuclear complexes with O,N-chelating
aminoalcohols apanadze, T. Sh.; Gulya, A. P.; Novotortsev, V. M.; Ellert, O.
G.; Shcherbakov, V. M.; Kokunov, Yu. V.; Bushaev, Yu. A. Koordinatsionnaya
Khimiya (1991), 17(7), 934-40.
4. Magnetic properties of cobalt complexes with amino alcohols, Evreev,
V. N.; Bogdanov, A. P. 13 Vses. Chugaev. Soveshch. po Khimii Kompleks.
Soedin., 1978 (1978), 137.
5.Synthesis, stereochemistry, and reactions of cobalt(III) complexes with
amino alcohol ligands
Okamoto, Martha S. No Corporate Source data available | (1974), 146 pp.
6.Synthesis and properties of isomeric tris(N-[2-hydroxyethyl]
ethylenediamine)cobalt(III) and tris(N-[2-hydroxypropyl]ethylenediamine)
cobalt(III) chlorides, arpeiskaya, E. I.; Kukushkin, Yu. N.; Trofimov, V. A.;
Yakovlev, I. P. , Zhurnal Neorganicheskoi Khimii (1971), 16(7), 1960-4。
Summary of the invention
It is desirable to provide chirality six [(R)-phenylalaninol] cobalt complex.To be solved technical problem is that a step
Synthesis obtains target product.
Chiral cobalt complex alleged by the present invention be by four acetate hydrate cobalts and D-phenylalaninol prepare by following chemistry
Compound shown in formula:
(I).
Chemical name: six [(R)-phenylalaninol] cobalt complex, is called for short coordination compound (I).
This coordination compound shows preferable catalytic performance in the Henle reaction of benzaldehyde, and its conversion ratio reaches 99%.
This synthetic method include synthesis and separate, its synthetic method be weigh 4.3811g (0.03mol) D-phenylalaninol and
2.4217g (0.01mol) four acetate hydrate cobalt is put in 100mL round-bottomed flask, and adds 30ml absolute methanol, and stirring makes them
Dissolve, and be heated to reflux 48h.After having reacted, filtered while hot so that it is volatilization naturally, there is aubergine crystal to separate out after a few days.
Synthetic reaction is as follows:
This synthetic method one step obtains target product, and technique is simple, easy to operate.
Accompanying drawing explanation
Fig. 1 is the single X-ray diffractometer figure of chirality six [(R)-phenylalaninol] cobalt complex.
Detailed description of the invention
The preparation of chirality six [(R)-phenylalaninol] cobalt acetate coordination compound:
Weigh 4.3811g (0.03mol) D-phenylalaninol and 2.4217g (0.01mol) four acetate hydrate cobalt puts into 100mL circle
In end flask, and adding 30ml absolute methanol, stirring makes them dissolve, and is heated to reflux 48h.After having reacted, filtered while hot,
Make it naturally volatilize, have aubergine crystal to separate out after a few days；Productivity: 36%；M.p.:79-82 ° of C;Specific rotatory power is [α]20 D=
370.8 °, (c 0.0712 CH3OH) Elemental analysis data [C54H72Co3N6O12]: theoretical value (%): C, 55.25; H,6.18;
N,7.16;Measured value (%): C, 54.88; H,6.38; N, 6.90；IR spectroscopic data (KBr; ν, cm-1): 3300,
1550,1310,1060,789,719,704；The crystal data of compound:
Empirical formula C54H72N6 O12Co3
Molecular weight 1186.06
Temperature 130 K
Wavelength 0.71073
Crystallographic system, Space group Monoclinic system, C 121
Cell parameter a=41.115 (7) alpha=90 deg.
b = 15.618 (3) Å beta = 107.774(2) deg.
c = 33.445(6) Å gamma = 90deg.
Volume 21463(7) ^3
Charge density 12,1.101 Mg/m^3
Absorption correction parameter 0.739 mm^-1
Number of electrons 7524 in unit cell
Crystal size 0.2x 0.15x 0.05 mm
Scope 0.609 to 27.613 at Theta angle
Index capture range-52≤h≤52 of HKL ,-20≤k < 18 ,-43≤l≤43
Collection/independent diffraction data 86640/45584 [R (int)=0.1378]
Data integrity degree 99.9 % of theta=30.5
The method Multi Slice Mode of absorption correction
The Matrix least square method of method F^2 that refine uses
Number/number of parameters 45584/479/1943 that data number/use limits
The concordance factor R 1=0.0888 of point diffraction, wR2=0.2052
The identical factor R 1=0.1966 of observable diffraction, wR2=0.2368
Absolute configuration parameter 0.088(16)
Maximum summit on difference Fourier figure and peak valley 0.877 and-0.754e. ^-3
Crystal typical bond distance data:
Co(1)-Co(2) 2.6460
Co(1)-O(1) 1.9412
Co(1)-O(2) 1.9130
Co(1)-O(3) 1.9492
Co(1)-N(1) 1.9361
Co(1)-N(2) 1.9499
Co(1)-N(3) 1.9467
Co(2)-Co(3) 2.6445
Co(2)-O(1) 2.1053
Co(2)-O(2) 2.0777
Co(2)-O(3) 2.1486
Co(2)-O(4) 2.1485
Co(2)-O(5) 2.0413
Co(2)-O(6) 2.1550
Co(3)-O(4) 1.9274
Co(3)-O(5) 1.9266
Co(3)-O(6) 1.9623
Co(3)-N(4) 1.9227
Co(3)-N(5) 1.9703
Co(3)-N(6) 1.9366
Crystal typical bond angle data
O(1)-Co(1)-Co(2) 51.9
O(1)-Co(1)-O(3) 85.7
O(1)-Co(1)-N(2) 93.4
O(1)-Co(1)-N(3) 172.3
O(2)-Co(1)-Co(2) 51.2
O(2)-Co(1)-O(1) 87.3
O(2)-Co(1)-O(3) 85.6
O(2)-Co(1)-N(1) 174.3
O(2)-Co(1)-N(2) 88.8
O(2)-Co(1)-N(3) 90.9
O(3)-Co(1)-Co(2) 53.2
O(3)-Co(1)-N(2) 174.3
N(1)-Co(1)-Co(2) 123.1
N(1)-Co(1)-O(1) 88.6
N(1)-Co(1)-O(3) 90.2
N(1)-Co(1)-N(2) 95.4
N(1)-Co(1)-N(3) 92.6
N(2)-Co(1)-Co(2) 122.2
N(3)-Co(1)-Co(2) 121.7
N(3)-Co(1)-O(3) 86.7
N(3)-Co(1)-N(2) 94.1
Co(3)-Co(2)-Co(1) 178.6
O(1)-Co(2)-Co(1) 46.5
O(1)-Co(2)-Co(3) 132.5
O(1)-Co(2)-O(3) 76.9
O(1)-Co(2)-O(4) 104.0
O(1)-Co(2)-O(6) 178.7
O(2)-Co(2)-Co(1) 45.8
O(2)-Co(2)-Co(3) 135.5
O(2)-Co(2)-O(1) 79.0
O(2)-Co(2)-O(3) 76.7
O(2)-Co(2)-O(4) 104.0
O(2)-Co(2)-O(6) 102.2
O(3)-Co(2)-Co(1) 46.6
O(3)-Co(2)-Co(3) 132.9
O(3)-Co(2)-O(6) 102.7
O(4)-Co(2)-Co(1) 134.5
O(4)-Co(2)-Co(3) 46.0
O(4)-Co(2)-O(3) 178.9
O(4)-Co(2)-O(6) 76.4
O(5)-Co(2)-Co(1) 132.2
O(5)-Co(2)-Co(3) 46.4
O(5)-Co(2)-O(1) 101.0
O(5)-Co(2)-O(2) 177.0
O(5)-Co(2)-O(3) 100.3
O(5)-Co(2)-O(4) 78.9
O(5)-Co(2)-O(6) 77.8
O(6)-Co(2)-Co(1) 134.0
O(6)-Co(2)-Co(3) 46.9
O(4)-Co(3)-Co(2) 53.3
O(4)-Co(3)-O(6) 86.3
O(4)-Co(3)-N(5) 95.2
O(4)-Co(3)-N(6) 173.1
O(5)-Co(3)-Co(2) 50.1
O(5)-Co(3)-O(4) 87.5
O(5)-Co(3)-O(6) 85.3
O(5)-Co(3)-N(5) 90.0
O(5)-Co(3)-N(6) 91.6
O(6)-Co(3)-Co(2) 53.3
O(6)-Co(3)-N(5) 175.1
N(4)-Co(3)-Co(2) 125.4
N(4)-Co(3)-O(4) 89.8
N(4)-Co(3)-O(5) 175.3
N(4)-Co(3)-O(6) 90.7
N(4)-Co(3)-N(5) 94.0
N(4)-Co(3)-N(6) 90.7
N(5)-Co(3)-Co(2) 124.3
N(6)-Co(3)-Co(2) 121.5
N(6)-Co(3)-O(6) 86.8
N(6)-Co(3)-N(5) 91.6
Co(1)-O(1)-Co(2) 81.6
C(1)-O(1)-Co(1) 106.2
C(1)-O(1)-Co(2) 121.0
Co(1)-O(2)-Co(2) 83.0
C(10)-O(2)-Co(1) 111.4
C(10)-O(2)-Co(2) 123.3
Co(1)-O(3)-Co(2) 80.3
C(19)-O(3)-Co(1) 110.2
C(19)-O(3)-Co(2) 121.5
Co(3)-O(4)-Co(2) 80.7
C(28)-O(4)-Co(2) 124.3
C(28)-O(4)-Co(3) 106.5
Co(3)-O(5)-Co(2) 83.5
C(37)-O(5)-Co(2) 123.7
C(37)-O(5)-Co(3) 107.6
Co(3)-O(6)-Co(2) 79.8
C(46)-O(6)-Co(2) 119.5
C(46)-O(6)-Co(3) 108.3
Co(1)-N(1)-H(1A) 110.2
Co(1)-N(1)-H(1B) 110.2
H(1A)-N(1)-H(1B) 108.5
C(2)-N(1)-Co(1) 107.6
C(2)-N(1)-H(1A) 110.2
C(2)-N(1)-H(1B) 110.2
Co(1)-N(2)-H(2A) 110.8
Co(1)-N(2)-H(2B) 110.8
H(2A)-N(2)-H(2B) 108.9
C(11)-N(2)-Co(1) 104.7
C(11)-N(2)-H(2A) 110.8
C(11)-N(2)-H(2B) 110.8
Co(1)-N(3)-H(3A) 109.8
Co(1)-N(3)-H(3B) 109.8
H(3A)-N(3)-H(3B) 108.3
C(20)-N(3)-Co(1) 109.3
C(20)-N(3)-H(3A) 109.8
C(20)-N(3)-H(3B) 109.8
Co(3)-N(4)-H(4A) 110.8
Co(3)-N(4)-H(4B) 110.8
H(4A)-N(4)-H(4B) 108.8
C(29)-N(4)-Co(3) 104.9
C(29)-N(4)-H(4A) 110.8
C(29)-N(4)-H(4B) 110.8
Co(3)-N(5)-H(5A) 110.7
Co(3)-N(5)-H(5B) 110.7
H(5A)-N(5)-H(5B) 108.8
C(38)-N(5)-Co(3) 105.1
C(38)-N(5)-H(5A) 110.7
C(38)-N(5)-H(5B) 110.7
Co(3)-N(6)-H(6A) 110.7
Co(3)-N(6)-H(6B) 110.7。
(3), Henle reaction application
2-nitro-1-phenylethanol
Catalyst I (0.050mmol), benzaldehyde 0.10 mL (0.986 mmol) and nitromethane (0.50 mL,
9.255 mmol) it is stirred at room temperature 6 h, monitor with nuclear-magnetism, conversion ratio: > 99 %,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)。
Claims (3)
1. a Chiral cobalt complex (I), its chemical formula is as follows:
(I).
2. the coordination compound (I) described in claim 1, at a temperature of 130 K, on the X-ray single crystal diffractometer of Oxford, with through stone
The MoK alpha ray (λ=0.71073) of ink monochromator monochromatization collects diffraction data with ω-θ scan mode, it is characterised in that brilliant
Body belongs to orthorhombic system, space group C 121, a=41.115 (7) alpha=90 deg； b = 15.618 (3) Å
beta = 107.774(2) deg；c = 33.445(6) Å gamma = 90deg.
3. the synthetic method of the coordination compound (I) described in claim 1, including synthesis and separation, it is characterised in that described synthesis
It is to weigh 4.3811g (0.03mol) D-phenylalaninol and 2.4217g (0.01mol) four acetate hydrate cobalt is put into 100mL round bottom and burnt
In Ping, and adding 30ml absolute methanol, stirring makes them dissolve, and is heated to reflux 48h；After having reacted, filtered while hot so that it is
Naturally volatilization, has aubergine crystal to separate out after a few days.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610386011.7A CN106008611B (en) | 2016-06-03 | 2016-06-03 | A kind of Chiral cobalt complex |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610386011.7A CN106008611B (en) | 2016-06-03 | 2016-06-03 | A kind of Chiral cobalt complex |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN106008611A true CN106008611A (en) | 2016-10-12 |
| CN106008611B CN106008611B (en) | 2018-05-25 |
Family
ID=57090390
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610386011.7A Active CN106008611B (en) | 2016-06-03 | 2016-06-03 | A kind of Chiral cobalt complex |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN106008611B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107337652A (en) * | 2017-07-05 | 2017-11-10 | 合肥祥晨化工有限公司 | A kind of Chiral oxazoline cobalt complex and purposes |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103342710A (en) * | 2013-07-29 | 2013-10-09 | 罗梅 | Chiral zinc complex |
| CN103450229A (en) * | 2013-07-29 | 2013-12-18 | 罗梅 | Application of chiral copper complex |
| CN103570768A (en) * | 2013-11-15 | 2014-02-12 | 合肥工业大学 | Cobalt-nitrogen complex |
-
2016
- 2016-06-03 CN CN201610386011.7A patent/CN106008611B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103342710A (en) * | 2013-07-29 | 2013-10-09 | 罗梅 | Chiral zinc complex |
| CN103450229A (en) * | 2013-07-29 | 2013-12-18 | 罗梅 | Application of chiral copper complex |
| CN103570768A (en) * | 2013-11-15 | 2014-02-12 | 合肥工业大学 | Cobalt-nitrogen complex |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107337652A (en) * | 2017-07-05 | 2017-11-10 | 合肥祥晨化工有限公司 | A kind of Chiral oxazoline cobalt complex and purposes |
Also Published As
| Publication number | Publication date |
|---|---|
| CN106008611B (en) | 2018-05-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Yutkin et al. | Synthesis and characterization of expected and unexpected topologies of homochiral porous metal (II) malate frameworks | |
| CN105669772A (en) | Preparation and synthesis method of nickel complex | |
| CN105712927B (en) | A kind of cobalt complex prepares and its synthetic method | |
| CN103613507B (en) | Chiral D-Phenylglycinol cobalt complex | |
| CN103570768B (en) | A kind of cobalt nitrogen complex | |
| Yuan et al. | A cuboidal [Ni 4 O 4] cluster as a precursor for recyclable, carbon-supported nickel nanoparticle reduction catalysts | |
| CN106008611A (en) | Chiral cobalt complex | |
| Srinivasan et al. | Synthesis, properties and supramolecular structure of di (aqua) bis (ethylenediamine) nickel (II) bis (4-nitrobenzoate) | |
| CN106117178A (en) | A kind of cobalt complex | |
| CN106220519A (en) | Preparation and synthesis method of cobalt complex | |
| CN103709204B (en) | A kind of cobalt complex, preparation method and its usage | |
| CN103570562A (en) | Chiral Ni complex | |
| CN104130293B (en) | A kind of three-dimensional coordination polymer of mixed ligand and preparation method thereof | |
| CN105669710B (en) | A kind of preparation of copper complex crystal and its synthetic method | |
| Nesterov et al. | Direct synthesis and crystal structures of new heteropolynuclear complexes containing aminoalcohol ligands: From heterobi-(Co/Zn) to heterotrimetallic (Cu/Co/Zn) compounds | |
| CN105111094B (en) | Preparation and synthesis method of chiral nickel complex crystal | |
| CN106117251B (en) | A kind of copper complex | |
| CN106083901A (en) | A kind of copper complex | |
| CN106083616A (en) | The preparation of a kind of cobalt complex and synthetic method | |
| CN103467311A (en) | Chiral cobalt complex | |
| CN106117250A (en) | Copper complex | |
| CN103553937B (en) | Chiral cobalt complex | |
| CN108467359A (en) | A kind of copper complex | |
| CN104311603A (en) | Sandwiched five-core nickel complex and preparation method thereof | |
| CN104130290B (en) | A kind of three-dimensional coordination polymer of two core clustering architectures and preparation method thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |