(4R,5S)-4-bromo-5-methyl-5-phenyldihydrofuran-2(3H)-one | 1548512-98-6

• 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: (4R,5S)-4-bromo-5-methyl-5-phenyldihydrofuran-2(3H)-one
• CAS: 1548512-98-6
• 化学式: C₁₁H₁₁BrO₂
• 分子量: 255.111
• InChiKey: XAPQKKVNTAYBRL-KOLCDFICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.61
• 重原子数：
  14.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  (E)-4-phenyl-3-pentenoic acid 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以91%的产率得到(4R,5S)-4-bromo-5-methyl-5-phenyldihydrofuran-2(3H)-one
  参考文献：
  名称：

  Molecular sieves as an efficient and recyclable catalyst for bromolactonization and bromoacetoxylation reactions

  摘要：

  Bromolactonization of unsaturated acids and bromoacetoxylation of olefins proceeded smoothly in the presence of molecular sieves and N-bromosuccinimide. The molecular sieves can be recycled and reused, and the halogen carrier can be recovered effectively. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.04.113

文献信息

• 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.
• Synthesis of chiral butenolides using amino-thiocarbamate-catalyzed asymmetric bromolactonization
  作者：Chong Kiat Tan、Jun Cheng Er、Ying-Yeung Yeung

  DOI：10.1016/j.tetlet.2014.01.009

  日期：2014.2

  The asymmetric cyclization of 4,4-disubstituted 3-butenoic acids is studied. Amino-thiocarbamates are used as the catalysts and N-bromosuccinimide is used as the stoichiometric halogen source. The resulting gamma-butanolide products are readily converted into the corresponding gamma-butenolides (up to 58% ee) derivatives in one-pot. (C) 2014 Elsevier Ltd. All rights reserved.