(3aS,5R,7R,7aR)-7-bromo-5-(2-propenyl)-7a-methyl-3a,4,5,6,7,7a-hexahydro-2(3H)benzofuranone | 744207-91-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: (3aS,5R,7R,7aR)-7-bromo-5-(2-propenyl)-7a-methyl-3a,4,5,6,7,7a-hexahydro-2(3H)benzofuranone
• 英文别名: (3aS,5R,7R,7aR)-7-bromo-7a-methyl-5-prop-1-en-2-yl-3,3a,4,5,6,7-hexahydro-1-benzofuran-2-one
• CAS: 744207-91-8
• 化学式: C₁₂H₁₇BrO₂
• 分子量: 273.17
• InChiKey: ZISXPZVXXWSNPM-DTHBNOIPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3aS,5R,7R,7aR)-7-bromo-5-(2-propenyl)-7a-methyl-3a,4,5,6,7,7a-hexahydro-2(3H)benzofuranone 在 potassium carbonate 、 臭氧 作用下， 以 二氯甲烷 为溶剂， 反应 1.25h， 生成 (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
• 作为产物：
  描述：

  (1R,5S)-香芹醇 在 N-溴代丁二酰亚胺(NBS) 、 丙酸 作用下， 以 丙酮 为溶剂， 反应 19.5h， 生成 (3aS,5R,7R,7aR)-7-bromo-5-(2-propenyl)-7a-methyl-3a,4,5,6,7,7a-hexahydro-2(3H)benzofuranone
  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.