(3R)-3-Bromo-1-[2-(diphenylphosphinyl)-6-methoxyphenyl]piperidine | 848850-67-9

• 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: (3R)-3-Bromo-1-[2-(diphenylphosphinyl)-6-methoxyphenyl]piperidine
• 英文别名: (3R)-3-bromo-1-(2-diphenylphosphoryl-6-methoxyphenyl)piperidine
• CAS: 848850-67-9
• 化学式: C₂₄H₂₅BrNO₂P
• 分子量: 470.346
• InChiKey: LCBZOQVDXDNAOL-LJQANCHMSA-N

物化性质

• 熔点：
  185-187 °C
• 沸点：
  631.2±55.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  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 四氢呋喃 、 间二甲苯 、 乙腈 为溶剂， 反应 12.33h， 生成 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：

  (S)-1-[2'-(diphenylphosphinyl)-6'-methoxyphenyl]-2-(hydroxymethyl)pyrrolidine 在 四溴化碳 、 三苯基膦 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以92%的产率得到(3R)-3-Bromo-1-[2-(diphenylphosphinyl)-6-methoxyphenyl]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

• 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).