[[(1R,4S,5S)-2-diphenylphosphoryl-4,5-dimethoxycyclopent-2-en-1-yl]methyl-phenylphosphoryl]benzene | 423773-02-8

• 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: [[(1R,4S,5S)-2-diphenylphosphoryl-4,5-dimethoxycyclopent-2-en-1-yl]methyl-phenylphosphoryl]benzene
• CAS: 423773-02-8
• 化学式: C₃₂H₃₂O₄P₂
• 分子量: 542.551
• InChiKey: KNRZLHITPZYBPE-JNGVYSEMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  38
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [[(1R,4S,5S)-2-diphenylphosphoryl-4,5-dimethoxycyclopent-2-en-1-yl]methyl-phenylphosphoryl]benzene 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以79%的产率得到[[(1R,2S,3S,5S)-5-diphenylphosphoryl-2,3-dimethoxycyclopentyl]methyl-phenylphosphoryl]benzene
  参考文献：
  名称：

  Synthesis and application of chiral bisphosphines through lithiation–conjugate addition tandem cyclization of chiral α,β,ψ,ω-unsaturated bisphosphine oxide

  摘要：

  用二异丙基酰胺锂处理非手性和手性δ,δ²,Ï,Ï-不饱和双膦氧化物时，会发生石化-共轭加成串联环化反应，生成相应的内δ,δ²-不饱和环状双膦氧化物；环化双膦氧化物的连续立体选择性还原得到了相应的反式和顺式双膦，这些双膦作为手性双膦配体成功地应用于催化不对称氢化反应。

  DOI：

  10.1039/b109269c
• 作为产物：
  描述：

  [[(1E,3S,4S,5E)-6-diphenylphosphoryl-3,4-dimethoxyhexa-1,5-dienyl]-phenylphosphoryl]benzene 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 以60%的产率得到[[(1R,4S,5S)-2-diphenylphosphoryl-4,5-dimethoxycyclopent-2-en-1-yl]methyl-phenylphosphoryl]benzene
  参考文献：
  名称：

  Conjugate reduction-initiated tandem cyclization of a chiral α,β,χ,ψ–unsaturated bisphosphine oxide

  摘要：

  Conjugate reduction-initiated cyclization of a chiral alpha,beta,chi,psi-unsaturated bisphosphine oxide,as developed by treating with lithium tri-siamylborohydride (LS-selectride") Lis a reducing agent to afford efficiently and selectively a carbocycle bearing bisphosphine appendage. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00787-6

文献信息

• Synthesis and application of chiral bisphosphines through lithiation–conjugate addition tandem cyclization of chiral α,β,ψ,ω-unsaturated bisphosphine oxide
  作者：Yasuo Nagaoka、Hideki Inoue、Nawal El-Koussi、Kiyoshi Tomioka

  DOI：10.1039/b109269c

  日期：2002.1.18

  Upon treatment with lithium diisopropylamide achiral and chiral α,β,ψ,ω-unsaturated bisphosphine oxides underwent lithiation–conjugate addition tandem cyclization to afford the corresponding endo-α,β-unsaturated cyclic bisphosphine oxides; sequential stereoselective reduction of the cyclized bisphosphine oxide gave the corresponding trans- and cis-bisphosphines that were successfully applicable in a catalytic asymmetric hydrogenation as chiral bisphosphine ligands.

  用二异丙基酰胺锂处理非手性和手性δ,δ²,Ï,Ï-不饱和双膦氧化物时，会发生石化-共轭加成串联环化反应，生成相应的内δ,δ²-不饱和环状双膦氧化物；环化双膦氧化物的连续立体选择性还原得到了相应的反式和顺式双膦，这些双膦作为手性双膦配体成功地应用于催化不对称氢化反应。
• Conjugate reduction-initiated tandem cyclization of a chiral α,β,χ,ψ–unsaturated bisphosphine oxide
  作者：Yasuo Nagaoka、Nawal El-Koussi、Shinichi Uesato、Kiyoshi Tomioka

  DOI：10.1016/s0040-4039(02)00787-6

  日期：2002.6

  Conjugate reduction-initiated cyclization of a chiral alpha,beta,chi,psi-unsaturated bisphosphine oxide,as developed by treating with lithium tri-siamylborohydride (LS-selectride") Lis a reducing agent to afford efficiently and selectively a carbocycle bearing bisphosphine appendage. (C) 2002 Elsevier Science Ltd. All rights reserved.