(1R,2S,4R,6S)-[4-acetyl-1-methyl-7-oxabicyclo[4.1.0]hept-2-yl]acetic acid methyl ester | 744207-83-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: (1R,2S,4R,6S)-[4-acetyl-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-acetyl-1-methyl-7-oxabicyclo[4.1.0]heptan-2-yl]acetate
• CAS: 744207-83-8
• 化学式: C₁₂H₁₈O₄
• 分子量: 226.273
• InChiKey: RYLHHPCXMWSKBM-FYLLDIAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  55.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,2S,4R,6S)-[4-acetyl-1-methyl-7-oxabicyclo[4.1.0]hept-2-yl]acetic acid methyl ester 在 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以70%的产率得到(1R,2S,4R,6S)-[4-acetoxy-1-methyl-7-oxabicyclo[4.1.0]hept-2-yl]acetic acid methyl ester
  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)-[1-methyl-4-(2-propenyl)-7-oxabicyclo[4.1.0]hept-2-yl]acetic acid methyl ester 在 臭氧 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以82%的产率得到(1R,2S,4R,6S)-[4-acetyl-1-methyl-7-oxabicyclo[4.1.0]hept-2-yl]acetic acid methyl ester
  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

文献信息

• Cp₂TiCl-Promoted Isomerization of Trisubstituted Epoxides to <i>e</i><i>xo</i>-Methylene Allylic Alcohols on Carvone Derivatives
  作者：Francisco Bermejo、Celso Sandoval

  DOI：10.1021/jo049358u

  日期：2004.8.1

  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.