4-diphenylphosphino-12-hydroxymethyl[2.2]paracyclophane | 727419-40-1

• 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: 4-diphenylphosphino-12-hydroxymethyl[2.2]paracyclophane
• 英文别名: (11-Diphenylphosphanyl-5-tricyclo[8.2.2.24,7]hexadeca-1(12),4,6,10,13,15-hexaenyl)methanol
• CAS: 727419-40-1
• 化学式: C₂₉H₂₇OP
• 分子量: 422.507
• InChiKey: BKUMSBVFKCBBMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-diphenylphosphino-12-hydroxymethyl[2.2]paracyclophane 在 sulfur 、 三溴化磷 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以85%的产率得到12-bromomethyl-4-diphenylthiophosphino[2.2]paracyclophane
  参考文献：
  名称：

  Synthesis of iridium complexes with new planar chiral chelating phosphinyl-imidazolylidene ligands and their application in asymmetric hydrogenation

  摘要：

  The synthesis of planar chiral phosphinoimidazolium salts such as (R-p)-3-(4-diphenyl-phosphino[2.2]paracyclophan-12-ylmethyl)-1-(2,6-diisopropylphenyl)imidazolium bromide (R-p)-11c starting from enantiopure 4,12-dibromo[2.2]paracyclophane (R-p)-6 is reported. After deprotonation of these salts and a subsequent reaction with [Ir(COD)Cl](2), chelating iridium imidazolylidene complexes (R-p)-5a-c are obtained. These complexes catalyze the asymmetric hydrogenation of functionalized and simple alkenes with up to 89% ee. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.03.047
• 作为产物：
  描述：

  rac-4-bromo[2.2]paracyclophan-13-ylenediphenylphosphine 在 lithium aluminium tetrahydride 、 正丁基锂 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 1.0h， 生成 4-diphenylphosphino-12-hydroxymethyl[2.2]paracyclophane
  参考文献：
  名称：

  Synthesis of iridium complexes with new planar chiral chelating phosphinyl-imidazolylidene ligands and their application in asymmetric hydrogenation

  摘要：

  The synthesis of planar chiral phosphinoimidazolium salts such as (R-p)-3-(4-diphenyl-phosphino[2.2]paracyclophan-12-ylmethyl)-1-(2,6-diisopropylphenyl)imidazolium bromide (R-p)-11c starting from enantiopure 4,12-dibromo[2.2]paracyclophane (R-p)-6 is reported. After deprotonation of these salts and a subsequent reaction with [Ir(COD)Cl](2), chelating iridium imidazolylidene complexes (R-p)-5a-c are obtained. These complexes catalyze the asymmetric hydrogenation of functionalized and simple alkenes with up to 89% ee. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.03.047

文献信息

• Synthesis of iridium complexes with new planar chiral chelating phosphinyl-imidazolylidene ligands and their application in asymmetric hydrogenation
  作者：Thilo Focken、Gerhard Raabe、Carsten Bolm

  DOI：10.1016/j.tetasy.2004.03.047

  日期：2004.6

  The synthesis of planar chiral phosphinoimidazolium salts such as (R-p)-3-(4-diphenyl-phosphino[2.2]paracyclophan-12-ylmethyl)-1-(2,6-diisopropylphenyl)imidazolium bromide (R-p)-11c starting from enantiopure 4,12-dibromo[2.2]paracyclophane (R-p)-6 is reported. After deprotonation of these salts and a subsequent reaction with [Ir(COD)Cl](2), chelating iridium imidazolylidene complexes (R-p)-5a-c are obtained. These complexes catalyze the asymmetric hydrogenation of functionalized and simple alkenes with up to 89% ee. (C) 2004 Elsevier Ltd. All rights reserved.