2-{[(S)-1-(2-Diphenylphosphanyl-6-methoxy-phenyl)-pyrrolidin-2-ylmethyl]-ethyl-amino}-ethanol | 848850-86-2

• 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: 2-{[(S)-1-(2-Diphenylphosphanyl-6-methoxy-phenyl)-pyrrolidin-2-ylmethyl]-ethyl-amino}-ethanol
• 英文别名: 2-[[(2S)-1-(2-diphenylphosphanyl-6-methoxyphenyl)pyrrolidin-2-yl]methyl-ethylamino]ethanol
• CAS: 848850-86-2
• 化学式: C₂₈H₃₅N₂O₂P
• 分子量: 462.572
• InChiKey: DFMIZAPZKSXDLG-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  35.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-{[(S)-1-(2-Diphenylphosphanyl-6-methoxy-phenyl)-pyrrolidin-2-ylmethyl]-ethyl-amino}-ethanol 、 乙酰氯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 以86%的产率得到Acetic acid 2-{[(S)-1-(2-diphenylphosphanyl-6-methoxy-phenyl)-pyrrolidin-2-ylmethyl]-ethyl-amino}-ethyl ester
  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：

  (3R)-3-Bromo-1-[2-(diphenylphosphinyl)-6-methoxyphenyl]piperidine 在 三氯硅烷 、 potassium carbonate 、 三乙胺 作用下， 以 间二甲苯 、 乙腈 为溶剂， 反应 12.0h， 生成 2-{[(S)-1-(2-Diphenylphosphanyl-6-methoxy-phenyl)-pyrrolidin-2-ylmethyl]-ethyl-amino}-ethanol
  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

• 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).