(E)-But-2-enoic acid (1R,2R,3S,5R)-2-hydroxy-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl ester | 500004-42-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (E)-But-2-enoic acid (1R,2R,3S,5R)-2-hydroxy-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl ester
• 英文别名: [(1R,2R,3S,5R)-2-hydroxy-2,6,6-trimethyl-3-bicyclo[3.1.1]heptanyl] (E)-but-2-enoate
• CAS: 500004-42-2
• 化学式: C₁₄H₂₂O₃
• 分子量: 238.327
• InChiKey: CZBUMXCUUOWTKC-PHMVSKTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  正丁基锂 、 (E)-But-2-enoic acid (1R,2R,3S,5R)-2-hydroxy-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl ester 在 copper(l) iodide 作用下， 以 乙醚 为溶剂， 反应 1.0h， 生成 (R)-3-Methyl-heptanoic acid (1R,2R,3S,5R)-2-hydroxy-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl ester
  参考文献：
  名称：

  The 1,4-addition of organometallic reagents to enoates derived from pinanediol

  摘要：

  The complex-induced, proximity effect-promoted 1,4-addition of (RCuBF3)-B-. and R2CuLi to enoates derived from (-)-pinanediol leads to adducts with the opposite sense of chirality (up to 98% d.e.). (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(02)00688-2
• 作为产物：
  描述：

  2-丁烯酰氯 、 (1R,2R,3S,5R)-(-)-2,3-蒎烷二醇 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以50%的产率得到(E)-But-2-enoic acid (1R,2R,3S,5R)-2-hydroxy-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl ester
  参考文献：
  名称：

  The 1,4-addition of organometallic reagents to enoates derived from pinanediol

  摘要：

  The complex-induced, proximity effect-promoted 1,4-addition of (RCuBF3)-B-. and R2CuLi to enoates derived from (-)-pinanediol leads to adducts with the opposite sense of chirality (up to 98% d.e.). (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(02)00688-2

文献信息

• The 1,4-addition of organometallic reagents to enoates derived from pinanediol
  作者：Sergio Pinheiro、Sérgio F. Pedraza、Mônica A. Peralta、Rafael C. Teixeira、Florence M.C. de Farias、Vı́tor F. Ferreira、Paulo R.R. Costa

  DOI：10.1016/s0957-4166(02)00688-2

  日期：2002.11

  The complex-induced, proximity effect-promoted 1,4-addition of (RCuBF3)-B-. and R2CuLi to enoates derived from (-)-pinanediol leads to adducts with the opposite sense of chirality (up to 98% d.e.). (C) 2002 Published by Elsevier Science Ltd.