ethyl (Z)-5-[(1R,5R,8R)-8-iodo-7-oxo-6-oxabicyclo[3.2.1]oct-2-en-1-yl]pent-2-enoate | 142612-49-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl (Z)-5-[(1R,5R,8R)-8-iodo-7-oxo-6-oxabicyclo[3.2.1]oct-2-en-1-yl]pent-2-enoate
• CAS: 142612-49-5；142697-19-6
• 化学式: C₁₄H₁₇IO₄
• 分子量: 376.191
• InChiKey: KRRCWHUVBPKPKH-DPKPIRSPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.56
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  3-[(1R,5R,8R)-8-iodo-7-oxo-6-oxabicyclo[3.2.1]oct-2-en-1-yl]propanal 、 乙氧甲酰基亚甲基三苯基膦 以 苯 为溶剂， 反应 2.0h， 以372 mg的产率得到rel-(1R(E),5R,8R)-ethyl 5-(8-iodo-7-oxo-6-oxabicyclo<3.2.1>oct-3-en-1-yl)-2-pentenoate
  参考文献：
  名称：

  Investigation of a model for 1,2-asymmetric induction in reactions of .alpha.-carbalkoxy radicals: a stereochemical comparison of reactions of .alpha.-carbalkoxy radicals and ester enolates

  摘要：

  The stereochemical course of reductions and allylations of alpha-carbalkoxy radicals with chiral centers at the beta-position are reported. Radicals without polar substituents, with alkoxyl or acetoxyl groups, and with hydroxyl groups at the beta-position were examined. Reactions showed selectivities ranging from low (50:50) to high (99:1). The results are discussed in terms of transition-state models that emphasize the importance of (1) allylic conformational analysis (minimization of A1,3 and A1,2 strain), (2) torisonal strain (minimization of eclipsed interactions), and (3) stereoelectronic effects.

  DOI：

  10.1021/jo00042a029