(2R,3R)-2,3-diphenylcyclopropane-1,1-dimethanol | 1259418-59-1

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 环丁烷木脂素
• 英文名称: (2R,3R)-2,3-diphenylcyclopropane-1,1-dimethanol
• 英文别名: [(2R,3R)-1-(hydroxymethyl)-2,3-diphenylcyclopropyl]methanol
• CAS: 1259418-59-1
• 化学式: C₁₇H₁₈O₂
• 分子量: 254.329
• InChiKey: JBADDOSFXCRODQ-HOTGVXAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  (2R,3R)-1-(ethoxycarbonyl)-2,3-diphenylcyclopropane-1-carboxylic acid 在 lithium aluminium tetrahydride 、 水 、 potassium hydroxide 作用下， 以 四氢呋喃 为溶剂， 以58%的产率得到(2R,3R)-2,3-diphenylcyclopropane-1,1-dimethanol
  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