甲基[(1R,2S,4R,6S)-4-羟基-1-甲基-7-氧杂双环[4.1.0]庚-2-基]乙酸酯 | 744207-92-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 中文名称: 甲基[(1R,2S,4R,6S)-4-羟基-1-甲基-7-氧杂双环[4.1.0]庚-2-基]乙酸酯
• 英文名称: (1R,2S,4R,6S)-[4-hydroxy-1-methyl-7-oxabicyclo[4.1.0]hept-2-yl]acetic acid methyl ester
• 英文别名: methyl 2-[(1R,2S,4R,6S)-4-hydroxy-1-methyl-7-oxabicyclo[4.1.0]heptan-2-yl]acetate
• CAS: 744207-92-9
• 化学式: C₁₀H₁₆O₄
• 分子量: 200.235
• InChiKey: CKJANVZPVXNNFW-PYHGXSLLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  59.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲基[(1R,2S,4R,6S)-4-羟基-1-甲基-7-氧杂双环[4.1.0]庚-2-基]乙酸酯 在 咪唑 、 titanocene dichloride 、 锌 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 methyl [(1S,2S,3S,5R)-5-tert-butyldimethylsilyloxy-3-hydroxy-2-methylcyclohexyl]acetate
  参考文献：
  名称：

  Cp₂TiCl-Promoted Isomerization of Trisubstituted Epoxides to exo-Methylene Allylic Alcohols on Carvone Derivatives

  摘要：

  The ring-opening reaction of trisubstituted epoxides promoted by Cp2TiCl led to exo-methylene allylic alcohols as major compounds when 0.5 M solutions of the epoxides were added to 0.1 M solutions of the reagent at room temperature in THF. In most cases, the allylic alcohols were contaminated with saturated alcohols. Normal and reverse addition modes led to the alternate product being favored. The different stereochemical outcome of cis- and trans-epoxy acetates is rationalized in terms of mechanistically biased elimination processes.

  DOI：

  10.1021/jo049358u
• 作为产物：
  描述：

  (1R,2S,4R,6S)-[4-acetoxy-1-methyl-7-oxabicyclo[4.1.0]hept-2-yl]acetic acid methyl ester 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.75h， 以92%的产率得到甲基[(1R,2S,4R,6S)-4-羟基-1-甲基-7-氧杂双环[4.1.0]庚-2-基]乙酸酯
  参考文献：
  名称：

  Cp₂TiCl-Promoted Isomerization of Trisubstituted Epoxides to exo-Methylene Allylic Alcohols on Carvone Derivatives

  摘要：

  The ring-opening reaction of trisubstituted epoxides promoted by Cp2TiCl led to exo-methylene allylic alcohols as major compounds when 0.5 M solutions of the epoxides were added to 0.1 M solutions of the reagent at room temperature in THF. In most cases, the allylic alcohols were contaminated with saturated alcohols. Normal and reverse addition modes led to the alternate product being favored. The different stereochemical outcome of cis- and trans-epoxy acetates is rationalized in terms of mechanistically biased elimination processes.

  DOI：

  10.1021/jo049358u