(1S,4R,5S,6R)-5,6-Dihydroxy-bicyclo[2.2.2]oct-2-ene-2,3-dicarboxylic acid dimethyl ester | 137927-45-8

• 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: (1S,4R,5S,6R)-5,6-Dihydroxy-bicyclo[2.2.2]oct-2-ene-2,3-dicarboxylic acid dimethyl ester
• 英文别名: dimethyl (1S,4R,5S,6R)-5,6-dihydroxybicyclo[2.2.2]oct-2-ene-2,3-dicarboxylate
• CAS: 137927-45-8
• 化学式: C₁₂H₁₆O₆
• 分子量: 256.255
• InChiKey: KCADHUMOAAMFPM-XCVPVQRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.61
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  93.06
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (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， 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：

  dimethyl bicyclo[2.2.2]octa-2,5-diene-2,3-dicarboxylate 在 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 水 、 丙酮 、 叔丁醇 为溶剂， 反应 43.0h， 以73%的产率得到(1S,4R,5S,6R)-5,6-Dihydroxy-bicyclo[2.2.2]oct-2-ene-2,3-dicarboxylic acid dimethyl 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