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1. WO2012065571 - CHIRAL SPIRO-PYRIDYLAMIDOPHOSPHINE LIGAND COMPOUND, SYNTHESIS METHOD THEREFOR AND APPLICATION THEREOF

Publication Number WO/2012/065571
Publication Date 24.05.2012
International Application No. PCT/CN2011/082432
International Filing Date 18.11.2011
IPC
C07F 9/58 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
FACYCLIC, CARBOCYCLIC, OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
9Compounds containing elements of Groups 5 or 15 of the Periodic System
02Phosphorus compounds
547Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
553having one nitrogen atom as the only ring hetero atom
576Six-membered rings
58Pyridine rings
B01J 31/24 2006.01
BPERFORMING OPERATIONS; TRANSPORTING
01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
31Catalysts comprising hydrides, coordination complexes or organic compounds
16containing coordination complexes
24Phosphines
C07B 53/00 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
BGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
53Asymmetric syntheses
C07C 29/145 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
29Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
132by reduction of an oxygen-containing functional group
136of C=O containing groups, e.g. -COOH
143of ketones
145with hydrogen or hydrogen-containing gases
C07C 33/22 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
33Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
18Monohydroxylic alcohols containing only six-membered aromatic rings as cyclic part
20monocyclic
22Benzylalcohol; Phenylethyl alcohol
C07C 33/18 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
33Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
18Monohydroxylic alcohols containing only six-membered aromatic rings as cyclic part
CPC
B01J 2231/643
BPERFORMING OPERATIONS; TRANSPORTING
01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
2231Catalytic reactions performed with catalysts classified in B01J31/00
60Reduction reactions, e.g. hydrogenation
64Reductions in general of organic substrates, e.g. hydride reductions or hydrogenations
641Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes
643of R2C=O or R2C=NR (R= C, H)
B01J 2531/827
BPERFORMING OPERATIONS; TRANSPORTING
01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
2531Additional information regarding catalytic systems classified in B01J31/00
80Complexes comprising metals of Group VIII as the central metal
82Metals of the platinum group
827Iridium
B01J 31/189
BPERFORMING OPERATIONS; TRANSPORTING
01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
31Catalysts comprising hydrides, coordination complexes or organic compounds
16containing coordination complexes
18containing nitrogen, phosphorus, arsenic or antimony ; as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
189containing both nitrogen and phosphorus as complexing atoms, including e.g. phosphino moieties, in one at least bidentate or bridging ligand
B01J 31/249
BPERFORMING OPERATIONS; TRANSPORTING
01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
31Catalysts comprising hydrides, coordination complexes or organic compounds
16containing coordination complexes
24Phosphines ; , i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
2404Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
2442comprising condensed ring systems
249Spiro-condensed ring systems
C07B 2200/07
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
BGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
2200Indexing scheme relating to specific properties of organic compounds
07Optical isomers
C07B 41/02
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
BGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
41Formation or introduction of functional groups containing oxygen
02of hydroxy or O-metal groups
Applicants
  • 浙江九洲药物科技有限公司 ZHEJIANG JIUZHOU PHARMA SCIENCE & TECHNOLOGY CO., LTD. [CN]/[CN] (AllExceptUS)
  • 周其林 ZHOU, Qilin [CN]/[CN] (UsOnly)
  • 谢建华 XIE, Jianhua [CN]/[CN] (UsOnly)
  • 刘晓艳 LIU, Xiaoyan [CN]/[CN] (UsOnly)
  • 谢剑波 XIE, Jianbo [CN]/[CN] (UsOnly)
  • 王立新 WANG, Lixin [CN]/[CN] (UsOnly)
Inventors
  • 周其林 ZHOU, Qilin
  • 谢建华 XIE, Jianhua
  • 刘晓艳 LIU, Xiaoyan
  • 谢剑波 XIE, Jianbo
  • 王立新 WANG, Lixin
Agents
  • 北京集佳知识产权代理有限公司 UNITALEN ATTORNEYS AT LAW
Priority Data
201010550836.019.11.2010CN
Publication Language Chinese (ZH)
Filing Language Chinese (ZH)
Designated States
Title
(EN) CHIRAL SPIRO-PYRIDYLAMIDOPHOSPHINE LIGAND COMPOUND, SYNTHESIS METHOD THEREFOR AND APPLICATION THEREOF
(FR) COMPOSÉ DE LIGAND SPIRO-PYRIDYLAMIDOPHOSPHINE CHIRAL, PROCÉDÉ DE SYNTHÈSE ET APPLICATION DE CELUI-CI
(ZH) 手性螺环吡啶胺基膦配体化合物与合成方法及其应用
Abstract
(EN)
The present invention relates to a chiral spiro-pyridylamidophosphine ligand compound, synthesis method therefor and application thereof. The chiral spiro-pyridylamidophosphine compound is a compound having a structure of Formula (I), a raceme or optical isomer thereof, or a catalytically acceptable salt thereof, and is mainly characterized by having a chiral spiro-dihydro-indene skeleton in its structure. The chiral spiro-pyridylamidophosphine compound may be synthesized with optical active7-diaryl/alkylphosphino-7'-amino-1,1'-spiro-dihydro-indene or substituted 7-diaryl/alkylphosphino-7'-amino-1,1'-spiro-dihydro-indene having a spiro-skeleton as chiral starting material. The chiral spiro-pyridylamidophosphine compound may be used as a chiral ligand in asymmetric hydrogenation of a carbonyl compound catalyzed by iridium, in which the reaction activity is very high, the amount of the catalyst may be 0.0001 mol%, and the enantioselectivity of the reaction is up to 99.9%ee.
(FR)
La présente invention concerne un composé de ligand spiro-pyridylamidophosphine chiral, un procédé de synthèse de celui-ci et l'application de celui-ci. Le composé spiro-pyridylamidophosphine chiral est un composé ayant une structure de formule (I), un racémique ou un isomère optique de celui-ci, ou un sel acceptable sur le plan catalytique de celui-ci, et est principalement caractérisé en ce qu'il a un squelette spiro-dihydro-indène dans sa structure. Le composé spiro-pyridylamidophosphine chiral peut être synthétisé avec un 7-diaryl/alkylphosphino-7'-amino-1,1'-spiro-dihydro-indène ou 7-diaryl/alkylphosphino-7'-amino-1,1'-spiro-dihydro-indène substitué optiquement actif ayant un spiro-squelette en tant que matériau de départ chiral. Le composé spiro-pyridylamidophosphine chiral peut être utilisé en tant que ligand chiral dans l'hydrogénation asymétrique d'un composé carbonyle catalysée par l'iridium, dans laquelle l'activité de réaction est très élevée, la quantité du catalyseur peut être de 0,0001 % en moles, et l'énantiosélectivité de la réaction est de jusqu'à 99,9 % en énantiomère.
(ZH)
本发明涉及一种手性螺环吡啶胺基膦配体化合物与合成方法及其应用。该手性螺环吡啶胺基膦化合物是具有式I结构的化合物,或其消旋体或旋光异构体,或其催化可接受的盐,主要结构特征是具有手性螺二氢茚骨架。该手性螺环吡啶胺基膦化合物可以由具有螺环骨架的光学活性的7-二芳/烷基膦基-7'-氨基-1,1'-螺二氢茚或取代的7-二芳/烷基膦基-7'-羧基-1,1'-螺二氢茚为手性起始原料合成。该手性螺环吡啶胺基膦化合物可作为手性配体用于铱催化的羰基化合物的不对称催化氢化反应中,反应的活性也很高,催化剂的用量可以为0.0001%摩尔,反应的对映选择性达到99.9%ee。
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