endo,cis-5,6-dimesyloxybicyclo<2.2.2>oct-2-ene | 137927-41-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: endo,cis-5,6-dimesyloxybicyclo<2.2.2>oct-2-ene
• 英文别名: [(1S,2R,3S,4R)-3-methylsulfonyloxy-2-bicyclo[2.2.2]oct-5-enyl] methanesulfonate
• CAS: 137927-41-4
• 化学式: C₁₀H₁₆O₆S₂
• 分子量: 296.365
• InChiKey: GPODJZITDBXVPX-YNFQOJQRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  重氮甲烷 、 endo,cis-5,6-dimesyloxybicyclo<2.2.2>oct-2-ene 反应 1080.0h， 以25%的产率得到Methanesulfonic acid (1S,2S,6R,7R,8S,9R)-8-methanesulfonyloxy-3,4-diaza-tricyclo[5.2.2.0^2,6]undec-3-en-9-yl ester
  参考文献：
  名称：

  Diastereofacial selectivity in 1,3-dipolar cycloadditions. Reactions of diazomethane with endo,cis-5,6-disubstituted bicyclo[2.2.2]oct-2-enes.

  摘要：

  The reaction of diazomethane with endo,cis-5,6-diacetoxy, dimesyloxy, bis(methoxycarbonyl) and dihydroxybicyclo[2.2.2]oct-2-ene derivatives, respectively, afforded either only the anti adduct or a mixture of anti and syn adducts wherein the anti diasteroisomer was highly dominant (greater-than-or-equal-to 10:1). The observed facial selectivity provides convincing evidence that direct through space interactions between the attacking 1,3-dipole and acetoxy, hydroxy etc. substituents are, as a whole, repulsive. Steric ''non-bonded'' repulsions and dipole-dipole interactions override possible stabilizing interactions, e.g. orbital interactions and hydrogen bonding effects.

  DOI：

  10.1016/s0040-4020(01)88294-6