(2S-cis)-2-<(dicyclohexylphosphino)-methyl>-4-(diphenylphosphino)-1-pyrrolidinecarboxylic acid 1,1-dimethylethyl ester | 110450-56-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (2S-cis)-2-<(dicyclohexylphosphino)-methyl>-4-(diphenylphosphino)-1-pyrrolidinecarboxylic acid 1,1-dimethylethyl ester
• 英文别名: (2S,4S)-N-(t-butoxycarbonyl)-2-<(dicyclohexylphosphino)methyl>-4-(diphenylphosphino)pyrrolidine；(2S,4S)-N-(t-butoxycarbonyl)-2-[(dicyclohexylphosphino)methyl]-4-(diphenylphosphino)pyrrolidine；tert-butyl (2S,4S)-2-(dicyclohexylphosphanylmethyl)-4-diphenylphosphanylpyrrolidine-1-carboxylate
• CAS: 110450-56-1
• 化学式: C₃₄H₄₉NO₂P₂
• 分子量: 565.716
• InChiKey: YIJKPVVURFMGSR-UCGGBYDDSA-N

物化性质

• 熔点：
  126-127 °C
• 沸点：
  644.1±48.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.64
• 重原子数：
  39.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  二氢-4,4-二甲基-2,3-呋喃二酮 、 (2S-cis)-2-<(dicyclohexylphosphino)-methyl>-4-(diphenylphosphino)-1-pyrrolidinecarboxylic acid 1,1-dimethylethyl ester 以9%的产率得到
  参考文献：
  名称：

  Morimoto Toshiaki, Takahashi Hisashi, Achiwa Kazuo, Chem. and Pharm. Bull, 42 (1994) N 3, S 481-488

  摘要：

  DOI：
• 作为产物：
  描述：

  (4R)-4-羟基-L-脯氨酸乙酯 生成 (2S-cis)-2-<(dicyclohexylphosphino)-methyl>-4-(diphenylphosphino)-1-pyrrolidinecarboxylic acid 1,1-dimethylethyl ester
  参考文献：
  名称：

  Morimoto Toshiaki, Takahashi Hisashi, Achiwa Kazuo, Chem. and Pharm. Bull, 42 (1994) N 3, S 481-488

  摘要：

  DOI：

文献信息

• Asymmetric Reactions Catalyzed by Chiral Metal Complex. LIX. Preparations of Chiral Pyrrolidinebisphosphines Bearing Two Different Types of Phosphino Groups and Their Use in Efficient Catalytic Asymmetric Hydrogenation.
  作者：Toshiaki MORIMOTO、Hisashi TAKAHASHI、Kazuo ACHIWA

  DOI：10.1248/cpb.42.481

  日期：——

  Chiral pyrrolidinebisphosphine ligands, (2S-cis)-BCPM and (2S-cis)-BCPP, bearing two different types of phosphino groups, a dicyclohexylphosphino group and a diphenylphosphino groups, were designed and prepared on the basis of our design concept for developing highly efficient ligands. The validity of the concept was confirmed experimentally in the asymmetric hydrogenation of ketopantolactone using neutral rhodium(I) complexes of BCPM, BCPP, BPPM, and BCCP. The rhodium(I) complex of (2S-cis)-BCPM was found to be the most effective catalyst (substrate/catalyst >ca. 104, >90%ee (R)).

  手性吡咯烷双磷配体（2S-cis）-BCPM 和（2S-cis）-BCPP，分别具有两种不同类型的磷基团：双环己基磷基团和二苯基磷基团，基于我们开发高效配体的设计理念进行了设计和制备。通过使用BCPM、BCPP、BPPM和BCCP的中性铑(I)配合物，在酮氨基酸内酯的非对称加氢反应中实验验证了该设计理念的有效性。研究发现（2S-cis）-BCPM的铑(I)配合物是最有效的催化剂（底物/催化剂 >约104，>90%酯选窗率 (R)）。
• Synthesis of a New Chiral Pyrrolidine Ligand Bearing Two Different Types of Phosphino Groups and Their Effects on the Asymmetric Hydrogenation of Ketopantolactone
  作者：Toshiaki Morimoto、Hisashi Takahashi、Katsuyasu Fujii、Mitsuo Chiba、Kazuo Achiwa

  DOI：10.1246/cl.1986.2061

  日期：1986.12.5

  The respective functions of the two phosphino groups of the pyrrolidinebisphosphine ligands in the asymmetric hydrogenation of ketopantolactone were elucidated.

  阐明了吡咯烷双膦配体的两个膦基在酮基内酯不对称氢化中的各自作用。
• MORIMOTO TOSHIAKI; TAKAHASHI HISASHI; FUJII KATSUYASU; CHIBA MITSUO; ACHI+, CHEM. LETT.,(1986) N 12, 2061-2064
  作者：MORIMOTO TOSHIAKI、 TAKAHASHI HISASHI、 FUJII KATSUYASU、 CHIBA MITSUO、 ACHI+

  DOI：——

  日期：——