(4S,5R)-5-Bromo-1-oxa-spiro[3.5]nonan-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (4S,5R)-5-Bromo-1-oxa-spiro[3.5]nonan-2-one
• 英文别名: (4S,5R)-5-bromo-1-oxaspiro[3.5]nonan-2-one
• 化学式: C₈H₁₁BrO₂
• 分子量: 219.078
• InChiKey: FKGASWWUBGIHFA-SVRRBLITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-环己烯基乙酸 在 thallium(I) carbonate 、 溴 作用下， 以 二氯甲烷 为溶剂， 以81%的产率得到(3aS,7aR)-3a-Bromo-hexahydro-benzofuran-2-one
  参考文献：
  名称：

  A Convenient Method for Bromolactonization

  摘要：

  溴内酯可以方便地从不饱和酸、溴和碳酸铊(I)中获得。

  DOI：

  10.1055/s-1988-27790

文献信息

• A Convenient Method for Bromolactonization
  作者：Richard C. Cambie、Peter S. Rutledge、Robyn F. Somerville、Paul D. Woodgate

  DOI：10.1055/s-1988-27790

  日期：——

  Bromolactones are conveniently obtained from unsaturated acids, bromine, and thallium(I) carbonate.

  溴内酯可以方便地从不饱和酸、溴和碳酸铊(I)中获得。
• Selenium-Catalyzed Halolactonization:  Nucleophilic Activation of Electrophilic Halogenating Reagents
  作者：Shelli R. Mellegaard、Jon A. Tunge

  DOI：10.1021/jo048460o

  日期：2004.12.1

  Diphenyl diselenide catalyzes the halolactonization of unsaturated acids with N-halosuccinimides under mild conditions. The diselenide not only accelerates the reactions, but in some cases affords regiocontrol in favor of gamma-lactone products. Experiments show that the regioselectivity in favor of gamma-lactones is a result of kinetic rather than thermodynamic control.
• Indole-Catalyzed Bromolactonization in Lipophilic Solvent: A Solid–Liquid Phase Transfer Approach
  作者：Tao Chen、Thomas Jian Yao Foo、Ying-Yeung Yeung

  DOI：10.1021/acscatal.5b01182

  日期：2015.8.7

  We have developed a novel indole-catalyzed bromolactonization of olefinic acids. The reaction could be conducted in lipophilic solvent through a solid liquid phase transfer mechanism. This catalytic protocol has been applied to the synthesis of base-sensitive bromolactones.