5-(chloromethyl)-4-methyldihydrofuran-2(3H)-one | 933460-77-6

• 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: 5-(chloromethyl)-4-methyldihydrofuran-2(3H)-one
• 英文别名: 5-(Chloromethyl)-4-methyloxolan-2-one
• CAS: 933460-77-6
• 化学式: C₆H₉ClO₂
• 分子量: 148.589
• InChiKey: LHZZSKBZAJYKRU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  3-甲基-4-戊烯酸 在 碘苯二乙酸 、 lithium chloride 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以80%的产率得到5-(chloromethyl)-4-methyldihydrofuran-2(3H)-one
  参考文献：
  名称：

  An effective method for the preparation of chlorolactones

  摘要：

  The effective chlorolactonization of alkenoic acids with (diacetoxyiodo)benzene and lithium chloride under mild conditions have been studied. Experiments show that various 4-pentenoic acids react with (diacetoxyiodo)benzene and lithium chloride fluently in CH3OH at room temperature, obtaining five-membered chlorolactones in good yields in short times. Other alkenoic acids, such as 3-butenoic acid and trans 3-hexenoic acid give some more complicated results, and 4-pentynoic acid provides a chloroenol lactone with Z configuration in 40% of yield. (C) 2010 Min Zhu. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2010.11.014

文献信息

• Indium chloride mediated chlorolactonization: construction of chlorinated lactone fragments
  作者：Hideki Abe、Naoki Fukazawa、Toyoharu Kobayashi、Hisanaka Ito

  DOI：10.1016/j.tet.2013.01.072

  日期：2013.3

  Chlorolactonization of unsaturated acids with chloramine-T catalyzed by indium chloride as a Lewis acid was demonstrated. This is a new synthetic methodology for the construction of chlorinated lactone frameworks from unsaturated acids. (C) 2013 Elsevier Ltd. All rights reserved.