(2R,3R)-1,1-bis[(diphenylphosphanyl)methyl]-2,3-bis(3',5'-diphenylphenyl)cyclopropane | 1268519-03-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: (2R,3R)-1,1-bis[(diphenylphosphanyl)methyl]-2,3-bis(3',5'-diphenylphenyl)cyclopropane
• 英文别名: [(2R,3R)-2,3-bis(3,5-diphenylphenyl)-1-(diphenylphosphanylmethyl)cyclopropyl]methyl-diphenylphosphane
• CAS: 1268519-03-4
• 化学式: C₆₅H₅₂P₂
• 分子量: 895.075
• InChiKey: OGAPQFNNZOREKA-VKOZLBNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.8
• 重原子数：
  67
• 可旋转键数：
  14
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  (3,5-二溴苄基)磷酸二乙酯 在 ruthenium trichloride 、 sodium tetrahydroborate 、 sodium periodate 、 四(三苯基膦)钯 、 氯化亚砜 、 甲基磺酰胺 、 三氟化硼乙醚 、 potassium tert-butylate 、 sodium hydride 、 potassium carbonate 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 作用下， 以 四氢呋喃 、 四氯化碳 、 乙二醇二甲醚 、 乙醇 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 、 叔丁醇 为溶剂， 反应 221.0h， 生成 (2R,3R)-1,1-bis[(diphenylphosphanyl)methyl]-2,3-bis(3',5'-diphenylphenyl)cyclopropane
  参考文献：
  名称：

  A novel C2-symmetric bisphosphane ligand with a chiral cyclopropane backbone: synthesis and application in the Rh(I)-catalyzed asymmetric 1,4-addition of arylboronic acids

  摘要：

  The synthesis of a novel C-2-symmetric bisphosphane ligand was accomplished starting from trans(2R,3R)-bis(3',5'-diphenylphenyl)cyclopropane-1,1-dimethanol as a key intermediate. This ligand was tested in the asymmetric rhodium(I)-catalyzed 1,4-addition to cyclic enones. We also compared the new ligand with a similar phosphane ligand with a less bulky cyclopropane backbone. Good yields (up to 99%) and enantioselectivities (up to 89% ee) were observed. We demonstrated that the presence of a more bulky cyclopropane backbone resulted in a less effective ligand. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.10.027
• 作为试剂：
  描述：

  2-环己烯-1-酮 、 苯硼酸 在 chlorobis(ethylene)rhodium(I) dimer 、 (2R,3R)-1,1-bis[(diphenylphosphanyl)methyl]-2,3-bis(3',5'-diphenylphenyl)cyclopropane 、 potassium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 3.0h， 生成 (R)-3-苯基环己酮 、 (S)-3-苯基环己酮
  参考文献：
  名称：

  A novel C2-symmetric bisphosphane ligand with a chiral cyclopropane backbone: synthesis and application in the Rh(I)-catalyzed asymmetric 1,4-addition of arylboronic acids

  摘要：

  The synthesis of a novel C-2-symmetric bisphosphane ligand was accomplished starting from trans(2R,3R)-bis(3',5'-diphenylphenyl)cyclopropane-1,1-dimethanol as a key intermediate. This ligand was tested in the asymmetric rhodium(I)-catalyzed 1,4-addition to cyclic enones. We also compared the new ligand with a similar phosphane ligand with a less bulky cyclopropane backbone. Good yields (up to 99%) and enantioselectivities (up to 89% ee) were observed. We demonstrated that the presence of a more bulky cyclopropane backbone resulted in a less effective ligand. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.10.027

文献信息

• A novel C2-symmetric bisphosphane ligand with a chiral cyclopropane backbone: synthesis and application in the Rh(I)-catalyzed asymmetric 1,4-addition of arylboronic acids
  作者：Yaşar Gök、Timothy Noël、Johan Van der Eycken

  DOI：10.1016/j.tetasy.2010.10.027

  日期：2010.12

  The synthesis of a novel C-2-symmetric bisphosphane ligand was accomplished starting from trans(2R,3R)-bis(3',5'-diphenylphenyl)cyclopropane-1,1-dimethanol as a key intermediate. This ligand was tested in the asymmetric rhodium(I)-catalyzed 1,4-addition to cyclic enones. We also compared the new ligand with a similar phosphane ligand with a less bulky cyclopropane backbone. Good yields (up to 99%) and enantioselectivities (up to 89% ee) were observed. We demonstrated that the presence of a more bulky cyclopropane backbone resulted in a less effective ligand. (C) 2010 Elsevier Ltd. All rights reserved.