(2R,3R)-1,1-bis(methanesulfonyloxymethyl)-2,3-diphenylcyclopropane | 1259418-60-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (2R,3R)-1,1-bis(methanesulfonyloxymethyl)-2,3-diphenylcyclopropane
• 英文别名: [(2R,3R)-1-(methylsulfonyloxymethyl)-2,3-diphenylcyclopropyl]methyl methanesulfonate
• CAS: 1259418-60-4
• 化学式: C₁₉H₂₂O₆S₂
• 分子量: 410.512
• InChiKey: MZUXASQQHPUHFG-ROUUACIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3R)-1,1-bis(methanesulfonyloxymethyl)-2,3-diphenylcyclopropane 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 反应 3.5h， 以89%的产率得到(2R,3R)-1,1-bis(azidomethyl)-2,3-diphenylcyclopropane
  参考文献：
  名称：

  trans-(2R,3R)-2,3-Diphenylcyclopropane-1,1-dimethanol: a pivotal diol for the synthesis of novel C2-symmetric ligands for asymmetric transition metal catalysis

  摘要：

  Various chiral ligands bearing phosphorus or nitrogen donor atoms were obtained in a straightforward manner starting from trans-(2R,3R)-diphenylcyclopropane-1,1-dimethanol as a key structure. These chiral ligands were tested and compared in palladium(0)-catalyzed asymmetric allylic alkylation reactions (up to 71% ee) and rhodium(1)-catalyzed asymmetric hydrogenations (up to 88% ee). Moreover, in the asymmetric allylic alkylation, we observed excellent activity with a diphosphinite ligand (TOF = 600 mol 17 x [mol Pd x h)(-1)]. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.08.007
• 作为产物：
  描述：

  (2R,3R)-2,3-diphenylcyclopropane-1,1-dimethanol 、 甲基磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.75h， 以97%的产率得到(2R,3R)-1,1-bis(methanesulfonyloxymethyl)-2,3-diphenylcyclopropane
  参考文献：
  名称：

  trans-(2R,3R)-2,3-Diphenylcyclopropane-1,1-dimethanol: a pivotal diol for the synthesis of novel C2-symmetric ligands for asymmetric transition metal catalysis

  摘要：

  Various chiral ligands bearing phosphorus or nitrogen donor atoms were obtained in a straightforward manner starting from trans-(2R,3R)-diphenylcyclopropane-1,1-dimethanol as a key structure. These chiral ligands were tested and compared in palladium(0)-catalyzed asymmetric allylic alkylation reactions (up to 71% ee) and rhodium(1)-catalyzed asymmetric hydrogenations (up to 88% ee). Moreover, in the asymmetric allylic alkylation, we observed excellent activity with a diphosphinite ligand (TOF = 600 mol 17 x [mol Pd x h)(-1)]. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.08.007

文献信息

• trans-(2R,3R)-2,3-Diphenylcyclopropane-1,1-dimethanol: a pivotal diol for the synthesis of novel C2-symmetric ligands for asymmetric transition metal catalysis
  作者：Elias Vervecken、Michel Van Overschelde、Timothy Noël、Yaşar Gök、Susana Alvárez Rodríguez、Simon Cogen、Johan Van der Eycken

  DOI：10.1016/j.tetasy.2010.08.007

  日期：2010.10

  Various chiral ligands bearing phosphorus or nitrogen donor atoms were obtained in a straightforward manner starting from trans-(2R,3R)-diphenylcyclopropane-1,1-dimethanol as a key structure. These chiral ligands were tested and compared in palladium(0)-catalyzed asymmetric allylic alkylation reactions (up to 71% ee) and rhodium(1)-catalyzed asymmetric hydrogenations (up to 88% ee). Moreover, in the asymmetric allylic alkylation, we observed excellent activity with a diphosphinite ligand (TOF = 600 mol 17 x [mol Pd x h)(-1)]. (C) 2010 Elsevier Ltd. All rights reserved.