BR112013021881A2 - catalisador para hidrogenação assimétrica de imina, método de síntese e aplicação do mesmo - Google Patents

catalisador para hidrogenação assimétrica de imina, método de síntese e aplicação do mesmo

Info

Publication number
BR112013021881A2
BR112013021881A2 BR112013021881A BR112013021881A BR112013021881A2 BR 112013021881 A2 BR112013021881 A2 BR 112013021881A2 BR 112013021881 A BR112013021881 A BR 112013021881A BR 112013021881 A BR112013021881 A BR 112013021881A BR 112013021881 A2 BR112013021881 A2 BR 112013021881A2
Authority
BR
Brazil
Prior art keywords
catalyst
group
aliphatic group
asymmetric
application
Prior art date
Application number
BR112013021881A
Other languages
English (en)
Other versions
BR112013021881B1 (pt
Inventor
Jin Li
Original Assignee
Dalian Heterogeneous Catalyst Co Ltd
Jiangsu Yangnong Chemical Ltd
Youth Chemical Co Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Dalian Heterogeneous Catalyst Co Ltd, Jiangsu Yangnong Chemical Ltd, Youth Chemical Co Ltd filed Critical Dalian Heterogeneous Catalyst Co Ltd
Publication of BR112013021881A2 publication Critical patent/BR112013021881A2/pt
Publication of BR112013021881B1 publication Critical patent/BR112013021881B1/pt

Links

Classifications

    • 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
    • B01J31/24—Phosphines, 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
    • B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
    • B01J31/2442—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems
    • B01J31/2461—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems and phosphine-P atoms as ring members in the condensed ring system or in a further ring
    • B01J31/2466—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems and phosphine-P atoms as ring members in the condensed ring system or in a further ring comprising aliphatic or saturated rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy 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
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing 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
    • B01J31/1845—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing 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 the ligands containing phosphorus
    • B01J31/185—Phosphites ((RO)3P), their isomeric phosphonates (R(RO)2P=O) and RO-substitution derivatives thereof
    • B01J31/186—Mono- or diamide derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/10—Preparation of carboxylic acid amides from compounds not provided for in groups C07C231/02 - C07C231/08
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
    • C07C251/04—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C251/06—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of a saturated carbon skeleton
    • C07C251/08—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of a saturated carbon skeleton being acyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/30—Hetero atoms other than halogen
    • C07D333/36—Nitrogen atoms
    • 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
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
    • C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
    • C07F9/657154—Cyclic esteramides of oxyacids of phosphorus
    • 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
    • B01J2231/60—Reduction reactions, e.g. hydrogenation
    • B01J2231/64—Reductions in general of organic substrates, e.g. hydride reductions or hydrogenations
    • B01J2231/641—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes
    • B01J2231/643—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes of R2C=O or R2C=NR (R= C, H)
    • 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
    • B01J2531/001—General concepts, e.g. reviews, relating to catalyst systems and methods of making them, the concept being defined by a common material or method/theory
    • B01J2531/002—Materials
    • B01J2531/007—Promoter-type Additives
    • 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
    • B01J2531/0261—Complexes comprising ligands with non-tetrahedral chirality
    • B01J2531/0266—Axially chiral or atropisomeric ligands, e.g. bulky biaryls such as donor-substituted binaphthalenes, e.g. "BINAP" or "BINOL"
    • 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
    • B01J2531/82—Metals of the platinum group
    • B01J2531/827—Iridium
    • 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
    • C07B2200/07—Optical isomers

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Materials Engineering (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)

Abstract

catalisador para hidrogenação assimétrica de imina, método de síntese e aplicação do mesmo a presente invenção refere-se a um composto de h~ 8~-binol bis-fosfina hidrogenada quiral, com a estrutura mostrada na fórmula (i) a seguir, onde tanto r^ 1^ quanto r^ 2^ são halogênio, h ou um grupo c~ 1~-c~ 10~ alifático; r^ 3^ é h ou um grupo c~ 1~-c~ 10~ alifático; r ^ 4^ é halogênio, amino, nitro, h, um grupo c~ 1~-c~ 10~ alifático ou um grupo c~ 1~-c~ 10~ alifático ou um grupo c~ 1~-c~ 10~ aromático; e x é fenila, fenila substituída, cicli-hexila, ciclo-hexila substituída, um grupo c~ 6~-c~ 30~ aromático, ou um grupo c~ 6~-c~ 30~ heterocíclico aromático contendo um ou mais heteroátomos selecionados dentre n, s, o. a presente invenção oferece ainda um catalisador para uma reação de hidrogenação catalítica assimétrica que contém o composto, onde o catalisador pode produzir mais de 90% de anantiômeros e eficiência com o número de turnover maior 100.000 na reação de hidrogenação assimétrica de iminas.
BR112013021881A 2011-02-28 2011-03-02 catalisador para hidrogenação assimétrica de imina, método de síntese e aplicação do mesmo BR112013021881B1 (pt)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CN2011100482405A CN102153589B (zh) 2011-02-28 2011-02-28 一种亚胺的不对称加氢催化剂及其合成方法和应用
PCT/CN2011/071448 WO2012116493A1 (zh) 2011-02-28 2011-03-02 一种亚胺的不对称加氢催化剂及其合成方法和应用

Publications (2)

Publication Number Publication Date
BR112013021881A2 true BR112013021881A2 (pt) 2016-10-25
BR112013021881B1 BR112013021881B1 (pt) 2018-10-09

Family

ID=44435297

Family Applications (1)

Application Number Title Priority Date Filing Date
BR112013021881A BR112013021881B1 (pt) 2011-02-28 2011-03-02 catalisador para hidrogenação assimétrica de imina, método de síntese e aplicação do mesmo

Country Status (6)

Country Link
US (1) US9358532B2 (pt)
CN (1) CN102153589B (pt)
AU (1) AU2011360843B2 (pt)
BR (1) BR112013021881B1 (pt)
CH (1) CH706430B1 (pt)
WO (1) WO2012116493A1 (pt)

Families Citing this family (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103570484A (zh) * 2012-08-07 2014-02-12 中国科学院大连化学物理研究所 一种高位阻手性芳香胺化合物的不对称氢化合成方法
CN104058984B (zh) * 2014-06-30 2015-12-30 罗梅 一种手性（s）-乙酰苯乙胺的合成方法及用途
PT108303A (pt) 2015-03-20 2016-09-20 Sapec Agro S A Processo de produção de (s)-metolacloro
CN106467473A (zh) * 2016-08-29 2017-03-01 江苏长青农化股份有限公司 精异丙甲草胺的合成方法
CN108299221A (zh) * 2017-01-13 2018-07-20 中国科学院成都有机化学有限公司 一种合成（s）-异丙甲草胺（金都尔）及其类似物的新方法
CN109422603A (zh) * 2017-08-29 2019-03-05 中国科学院大连化学物理研究所 一种铱催化不对称氢化亚胺合成手性胺化合物的方法
CN110551036B (zh) * 2018-05-31 2022-04-12 中国科学院大连化学物理研究所 一种铱/手性亚磷酸酯-吡啶催化亚胺不对称氢化方法
CN110551034B (zh) * 2018-05-31 2021-11-09 中国科学院大连化学物理研究所 一种酮的不对称还原胺化方法
CN110548546A (zh) * 2018-05-31 2019-12-10 中国科学院大连化学物理研究所 一种铱/线型膦-亚磷酰胺体系催化亚胺不对称氢化方法
CN110551032B (zh) * 2018-05-31 2021-11-09 中国科学院大连化学物理研究所 铱手性膦-胺基膦配体体系催化酮的不对称还原胺化方法
CN109096137A (zh) * 2018-07-30 2018-12-28 山东万豪肥业有限公司 一种精异丙甲草胺的合成方法
CN110026244B (zh) * 2019-04-22 2021-06-18 郑州大学 腈的α烷基化反应催化剂及其应用
CN112521333A (zh) * 2019-09-17 2021-03-19 中国科学院大连化学物理研究所 一种手性2,3-二取代四氢喹啉衍生物的合成方法
CN112538096B (zh) * 2020-11-30 2022-08-23 上海应用技术大学 一种含邻位碳硼烷基苯并噁唑结构的半夹心铑配合物的应用
CN113244951B (zh) * 2021-02-24 2022-04-12 天津商业大学 介孔分子筛负载的催化剂及其应用
CN112973789B (zh) * 2021-02-24 2021-08-06 天津商业大学 新介孔材料负载的催化剂及其应用
GB202104413D0 (en) * 2021-03-29 2021-05-12 Syngenta Crop Protection Ag Process for producing naa and (s)-naa
CN113754552A (zh) * 2021-09-18 2021-12-07 江苏长青农化南通有限公司 一种s-异丙甲草胺的合成方法
CN114085251B (zh) * 2021-11-02 2024-01-19 中国人民解放军空军军医大学 一类手性二茂铁-螺环骨架双膦配体及其制备方法
CN115260238A (zh) * 2022-07-22 2022-11-01 西北农林科技大学 一种亚磷酰胺双膦配体及其制备和应用
CN115417777B (zh) * 2022-08-02 2024-08-02 西安近代化学研究所 一种(s)-2-乙基-n-(1-甲氧基-2-丙基)-6-甲基苯胺的制备方法

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0256982B1 (de) 1986-08-04 1991-08-28 Ciba-Geigy Ag Verfahren zur Herstellung von optisch aktiven sekundären Arylaminen
US5011995A (en) 1987-07-28 1991-04-30 Ciba-Geigy Corporation Process for the preparation of optically active secondary amines
US5112999A (en) 1989-09-18 1992-05-12 Ciba-Geigy Corporation Iridium complexes, process for their preparation and their use
SG42938A1 (en) 1993-02-26 1997-10-17 Ciba Geigy Ag Ferrocenc diphosphines as ligands for homogeneous catalysts
UA51652C2 (uk) 1995-06-08 2002-12-16 Новартіс Аг Спосіб гідрування імінів
HRP960295A2 (en) 1995-07-06 1997-08-31 Ciba Geigy Ag Process for the hydrogenation of imines in the presence of immobilized iridium-diphosphine catalysts
HRP960302A2 (en) 1995-07-26 1998-04-30 Ciba Geigy Ag Process for the hydrogenation of imines
EP0850241B1 (en) 1995-07-27 2001-08-29 Novartis AG Iridium-diphosphine complexes and process for the hydrogenation of imines
FR2795332B1 (fr) 1999-06-22 2001-08-10 Look Fixations Sa Fixation pour engin de sport de neige
CN100467479C (zh) * 2005-10-20 2009-03-11 中国科学院大连化学物理研究所 一种膦-亚磷酰胺酯配体和制备方法及应用
CN101857612B (zh) 2010-06-11 2016-03-23 南京工业大学 一类手性双膦配体及其铱复合催化剂、制备方法及在不对称氢化合成(s)-异丙甲草胺中的应用

Also Published As

Publication number Publication date
US9358532B2 (en) 2016-06-07
BR112013021881B1 (pt) 2018-10-09
CN102153589A (zh) 2011-08-17
CN102153589B (zh) 2013-01-02
AU2011360843A1 (en) 2013-09-12
US20140018548A1 (en) 2014-01-16
CH706430B1 (fr) 2015-02-27
WO2012116493A1 (zh) 2012-09-07
AU2011360843B2 (en) 2016-05-12

Similar Documents

Publication Publication Date Title
BR112013021881A2 (pt) catalisador para hidrogenação assimétrica de imina, método de síntese e aplicação do mesmo
BRPI0702269A (pt) alcanolamidas e uso do mesmo como aditivos de combustìvel
EA201070451A1 (ru) Амидные соединения
BRPI0813284A8 (pt) Processo para a preparação de um composto da fórmula (i) e composto
BR112012028630A2 (pt) dispositivo para comprimir e secar gás
MX2010007587A (es) Compuestos que comprenden un grupo ciclobutoxi.
BR112014030260A2 (pt) método para converter um material hidrocarbonáceo em um produto de hidrocarboneto fluido que compreende p-xileno
DE602007004494D1 (de) Herstellung von (2r,3r)-3-(3-methoxyphenyl)-n,n,2- trimethylpentanamin
BR112012020983A2 (pt) processo para a preparação de derivados isoxazolina
BR112012032276A2 (pt) composições de combustível compreendendo derivados de isopreno
BR112015009800A2 (pt) processo melhorado de conversão de uma carga contendo a biomassa para a produção de hidrocarbonetos por via de síntese fischer-tropsch
BR112015011740A2 (pt) síntese de derivados de isoxazolina espirocíclicos
BR112013031405A2 (pt) piridopirazinas substituídas como novos inibidores de syk
EA201201581A1 (ru) Твердый основный катализатор
EA200900397A1 (ru) Новые соединения диосметина, способ их получения и фармацевтические композиции, которые их содержат
BR112013028486A2 (pt) método para promover crescimento de planta
BR112012025729A2 (pt) purificação por adsorção de caramelo
BR112015018160A2 (pt) processo para a preparação de sais de ácido diamínico/dicarboxílico e respectivas poliamidas
BR112012033690A2 (pt) sais de cálcio de compostos como agentes anti-inflamatórios, imunomodulares e antitroliferativos
BR112014032042A2 (pt) método de preparação de um suporte catalítico modificado, método de preparação de um precursor catalítico, método de preparação de um catalisador e processo de síntese de hidrocarbonetos
BR112016000968A2 (pt) Processo para a preparação de bifenilanilidas halogenadas
BR112015011974A2 (pt) derivados de azaquinazolina carboxamida
EA201591081A1 (ru) Молекулярное сито sapo-34 с использованием дигликольамина в качестве матричного агента и способ его получения
BR112013005823B8 (pt) Compostos heterocíclicos para o tratamento ou prevenção de distúrbios causados pela neurotransmissão reduzida de serotonina, norefnefrina ou dopamina
BR112015006263A2 (pt) método para usar um composto com carbono de michael para reduzir transferência de calor

Legal Events

Date Code Title Description
B07A Application suspended after technical examination (opinion) [chapter 7.1 patent gazette]
B09A Decision: intention to grant [chapter 9.1 patent gazette]
B16A Patent or certificate of addition of invention granted [chapter 16.1 patent gazette]

Free format text: PRAZO DE VALIDADE: 20 (VINTE) ANOS CONTADOS A PARTIR DE 02/03/2011, OBSERVADAS AS CONDICOES LEGAIS.