(1S,2R,6R,7R,8S,9R)-9-Acetoxy-3-acetyl-8-methoxy-3,4-diaza-tricyclo[5.2.2.0^2,6]undec-4-ene-2,6-dicarboxylic acid dimethyl ester | 137927-64-1

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (1S,2R,6R,7R,8S,9R)-9-Acetoxy-3-acetyl-8-methoxy-3,4-diaza-tricyclo[5.2.2.0^2,6]undec-4-ene-2,6-dicarboxylic acid dimethyl ester
• CAS: 137927-64-1
• 化学式: C₁₈H₂₄N₂O₈
• 分子量: 396.397
• InChiKey: VQSGPCLKKVNALM-SZNCOTQGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.11
• 重原子数：
  28.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  120.8
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  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 (1S,2R,6R,7R,8S,9R)-9-Acetoxy-3-acetyl-8-methoxy-3,4-diaza-tricyclo[5.2.2.0^2,6]undec-4-ene-2,6-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