(1R,4S,5R,6S)-5-Hydroxy-6-methoxy-bicyclo[2.2.2]oct-2-ene-2,3-dicarboxylic acid dimethyl ester | 137927-60-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (1R,4S,5R,6S)-5-Hydroxy-6-methoxy-bicyclo[2.2.2]oct-2-ene-2,3-dicarboxylic acid dimethyl ester
• CAS: 137927-60-7
• 化学式: C₁₃H₁₈O₆
• 分子量: 270.282
• InChiKey: ZAXVJSIAKXZREO-HJGGDWJDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.04
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  82.06
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (1R,4S,5R,6S)-5-Hydroxy-6-methoxy-bicyclo[2.2.2]oct-2-ene-2,3-dicarboxylic acid dimethyl ester 以 乙醚 为溶剂， 反应 168.0h， 生成
  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
• 作为产物：
  描述：

  重氮甲烷 、 (1S,4R,5S,6R)-5,6-Dihydroxy-bicyclo[2.2.2]oct-2-ene-2,3-dicarboxylic acid dimethyl ester 以 乙醚 为溶剂， 反应 63.0h， 以18.5%的产率得到methyl (1S,2R,6S,9S,10R,13R)-13-hydroxy-7-oxo-8-oxa-3,4-diazatetracyclo[7.3.1.02,6.06,10]tridec-3-ene-2-carboxylate
  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