di-(-)-bornyl (2R)-2-phenylcyclopropane-1,1-dicarboxylate | 1187486-38-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: di-(-)-bornyl (2R)-2-phenylcyclopropane-1,1-dicarboxylate
• CAS: 1187486-38-9
• 化学式: C₃₁H₄₂O₄
• 分子量: 478.672
• InChiKey: ZRLJHSVFFHICIX-KDEPCEFNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.68
• 重原子数：
  35.0
• 可旋转键数：
  5.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  di-(-)-bornyl (2R)-2-phenylcyclopropane-1,1-dicarboxylate 在 lithium aluminium tetrahydride 、 氯化铵 作用下， 以 四氢呋喃 、 乙醚 、 水 为溶剂， 以92%的产率得到[(2R)-2-phenylcyclopropane-1,1-diyl]dimethanol
  参考文献：
  名称：

  Preparation of both enantiomers of cyclopropane derivatives from the reaction of vinyl selenones with di-(−)-bornyl malonate

  摘要：

  The reaction of vinyl selenones with di-(-)-bornyl malonate and sodium hydride occurred with low diastereoselectivity and afforded a mixture of two diastereomeric cyclopropane derivatives in comparable yields. These, however, could be easily separated by chromatography. Removal of the bornyl group afforded highly enantiomerically enriched cyclopropanes. An example of the simple conversions of these cyclopropanes into useful cyclopropane alpha-amino acids is also illustrated. The syntheses of several vinyl selenides and selenones are also described. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.05.019
• 作为产物：
  描述：

  di-(-)-bornyl malonate 、 (E)-β-styryl phenyl selenone 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 di-(-)-bornyl (2S)-2-phenylcyclopropane-1,1-dicarboxylate 、 di-(-)-bornyl (2R)-2-phenylcyclopropane-1,1-dicarboxylate
  参考文献：
  名称：

  Preparation of both enantiomers of cyclopropane derivatives from the reaction of vinyl selenones with di-(−)-bornyl malonate

  摘要：

  The reaction of vinyl selenones with di-(-)-bornyl malonate and sodium hydride occurred with low diastereoselectivity and afforded a mixture of two diastereomeric cyclopropane derivatives in comparable yields. These, however, could be easily separated by chromatography. Removal of the bornyl group afforded highly enantiomerically enriched cyclopropanes. An example of the simple conversions of these cyclopropanes into useful cyclopropane alpha-amino acids is also illustrated. The syntheses of several vinyl selenides and selenones are also described. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.05.019