1-{(S)-1-[2-(Diphenyl-phosphinoyl)-6-methoxy-phenyl]-pyrrolidin-2-ylmethyl}-piperidine | 848850-72-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-{(S)-1-[2-(Diphenyl-phosphinoyl)-6-methoxy-phenyl]-pyrrolidin-2-ylmethyl}-piperidine
• 英文别名: 1-[[(2S)-1-(2-diphenylphosphoryl-6-methoxyphenyl)pyrrolidin-2-yl]methyl]piperidine
• CAS: 848850-72-6
• 化学式: C₂₉H₃₅N₂O₂P
• 分子量: 474.583
• InChiKey: IRMVZRPIGXTVCR-DEOSSOPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  32.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-{(S)-1-[2-(Diphenyl-phosphinoyl)-6-methoxy-phenyl]-pyrrolidin-2-ylmethyl}-piperidine 在 三氯硅烷 、 三乙胺 作用下， 以 间二甲苯 为溶剂， 反应 6.0h， 以88%的产率得到1-[(S)-1-(2-Diphenylphosphanyl-6-methoxy-phenyl)-pyrrolidin-2-ylmethyl]-piperidine
  参考文献：
  名称：

  Amination of N-Aryl Prolinol via Ring Expansion and Contraction:  Application to the Chiral Ligand for the Catalytic Asymmetric Reaction

  摘要：

  Chiral diaminophosphines 4 were prepared from (S)-prolinol-derived aminophosphine oxide 5 by bromination with ring expansion followed by amination with ring contraction and reduction, using trichlorosilane. In the presence of 4 as ligand, palladium-catalyzed asymmetric allylic alkylation of 1,3-diphenyl-2-propenyl acetate (11) with a dialkyl malonate-BSA-LiOAc system was successfully carried out with good enantioselectivities (up to 98% ee).

  DOI：

  10.1021/jo0479967
• 作为产物：
  描述：

  (S)-1-[2'-(diphenylphosphinyl)-6'-methoxyphenyl]-2-(hydroxymethyl)pyrrolidine 在 四溴化碳 、 potassium carbonate 、 三苯基膦 作用下， 以 乙腈 为溶剂， 反应 9.0h， 生成 1-{(S)-1-[2-(Diphenyl-phosphinoyl)-6-methoxy-phenyl]-pyrrolidin-2-ylmethyl}-piperidine
  参考文献：
  名称：

  Amination of N-Aryl Prolinol via Ring Expansion and Contraction:  Application to the Chiral Ligand for the Catalytic Asymmetric Reaction

  摘要：

  Chiral diaminophosphines 4 were prepared from (S)-prolinol-derived aminophosphine oxide 5 by bromination with ring expansion followed by amination with ring contraction and reduction, using trichlorosilane. In the presence of 4 as ligand, palladium-catalyzed asymmetric allylic alkylation of 1,3-diphenyl-2-propenyl acetate (11) with a dialkyl malonate-BSA-LiOAc system was successfully carried out with good enantioselectivities (up to 98% ee).

  DOI：

  10.1021/jo0479967

文献信息

• Chiral diaminophosphine ligands with stable C(aryl)N(amine) axial chirality derived from prolinol
  作者：Takashi Mino、Youichi Tanaka、Yutaka Sato、Akio Saito、Masami Sakamoto、Tsutomu Fujita

  DOI：10.1016/s0040-4039(03)01097-9

  日期：2003.6

  New type chiral ligands 3, which have a chiral carbon center and stable C(aryl)-N(amine) axial chirality, were prepared from chiral prolinol-derived aminophosphine oxide 4. Pd-catalyzed asymmetric allylic alkylation of 1,3-diphenyl-2-propenyl acetate (6) with a dimethyl malonate-BSA-LiOAc system was successfully carried out in the presence of 3d resulting in a good yield with good enantioselectivity (up to 95% ee). (C) 2003 Elsevier Science Ltd. All rights reserved.
• Amination of <i>N</i>-Aryl Prolinol via Ring Expansion and Contraction:  Application to the Chiral Ligand for the Catalytic Asymmetric Reaction
  作者：Takashi Mino、Akio Saito、Youichi Tanaka、Shintaro Hasegawa、Yutaka Sato、Masami Sakamoto、Tsutomu Fujita

  DOI：10.1021/jo0479967

  日期：2005.3.1

  Chiral diaminophosphines 4 were prepared from (S)-prolinol-derived aminophosphine oxide 5 by bromination with ring expansion followed by amination with ring contraction and reduction, using trichlorosilane. In the presence of 4 as ligand, palladium-catalyzed asymmetric allylic alkylation of 1,3-diphenyl-2-propenyl acetate (11) with a dialkyl malonate-BSA-LiOAc system was successfully carried out with good enantioselectivities (up to 98% ee).