(R)-1,2-bis-(diphenylphosphino)-3-phenyl-propane | 77656-97-4

• 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: (R)-1,2-bis-(diphenylphosphino)-3-phenyl-propane
• 英文别名: [(2R)-3-Phenylpropane-1,2-diyl]bis(diphenylphosphane)；[(2R)-1-diphenylphosphanyl-3-phenylpropan-2-yl]-diphenylphosphane
• CAS: 77656-97-4
• 化学式: C₃₃H₃₀P₂
• 分子量: 488.549
• InChiKey: MERDFPRZMPWARC-MGBGTMOVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  silver hexafluoroantimonate 、 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 (R)-1,2-bis-(diphenylphosphino)-3-phenyl-propane 、 水 以 丙酮 为溶剂， 以82%的产率得到(S(Rh)R(C))-[(η5-pentamethylcyclopentadienyl)Rh(benphos)(H2O)](SbF6)2
  参考文献：
  名称：

  Enantioselective Catalysts for the Diels–Alder Reaction between Methacrolein and Cyclopentadiene Based on the Chiral Fragment (η⁵-C₅Me₅)M(chiral diphosphane) (M = Rh, Ir)

  摘要：

  The aqua complexes [(eta(5)-C5Me5)M(PP*)-(H2O)][SbF6](2) (M = Rh, Ir; PP* = chiral diphosphane) (1-10) are prepared and characterized. These complexes efficiently catalyze the Diels-Alder reaction between methacrolein and HCp with enantioselectivities of up to 96% e.e. The norphos complexes 9 and 10, which are obtained as diastereomeric mixtures of the two epimers at the metal, afford the highest e.e. values. The intermediate complexes [(eta(5)-C5Me5)M(PP*)-(methacrolein)] [SbF6](2) (11-20) are also isolated and characterized, including the molecular structure determination of the [(eta(5-CMe5)-Me-5)M(benphos)(methacrolein)][SbF6](2) (M = Rh (13), Ir (14)) derivatives. An NMR study of the reactivity of the metallic intermediates under catalytic conditions explains the high enantioselectivities achieved with the norphos systems.

  DOI：

  10.1021/om200859z

文献信息

• Optisch aktive 1,2-Bis(diphenylphosphino)-verbindungen, diese als chirale Liganden enthaltende Metallkomplexe und deren Verwendung
  申请人：Degussa Aktiengesellschaft

  公开号：EP0031877B1

  公开（公告）日：1983-02-02
• US4356324A
  申请人：——

  公开号：US4356324A

  公开（公告）日：1982-10-26
• Enantioselective Catalysts for the Diels–Alder Reaction between Methacrolein and Cyclopentadiene Based on the Chiral Fragment (η⁵-C₅Me₅)M(chiral diphosphane) (M = Rh, Ir)
  作者：Daniel Carmona、Fernando Viguri、Ainara Asenjo、M. Pilar Lamata、Fernando Lahoz、Pilar Garcı́a-Orduña、L. A. Oro

  DOI：10.1021/om200859z

  日期：2011.12.26

  The aqua complexes [(eta(5)-C5Me5)M(PP*)-(H2O)][SbF6](2) (M = Rh, Ir; PP* = chiral diphosphane) (1-10) are prepared and characterized. These complexes efficiently catalyze the Diels-Alder reaction between methacrolein and HCp with enantioselectivities of up to 96% e.e. The norphos complexes 9 and 10, which are obtained as diastereomeric mixtures of the two epimers at the metal, afford the highest e.e. values. The intermediate complexes [(eta(5)-C5Me5)M(PP*)-(methacrolein)] [SbF6](2) (11-20) are also isolated and characterized, including the molecular structure determination of the [(eta(5-CMe5)-Me-5)M(benphos)(methacrolein)][SbF6](2) (M = Rh (13), Ir (14)) derivatives. An NMR study of the reactivity of the metallic intermediates under catalytic conditions explains the high enantioselectivities achieved with the norphos systems.