2-chloromethyl-2,3-dihydropyran-4-one | 134387-58-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 2-chloromethyl-2,3-dihydropyran-4-one
• 英文别名: 2-(Chloromethyl)-2,3-dihydropyran-4-one
• CAS: 134387-58-9
• 化学式: C₆H₇ClO₂
• mdl: MFCD19235261
• 分子量: 146.573
• InChiKey: GTZBXXYQRFEAQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  氯乙醛 、 反-1-甲氧基-3-(三甲基硅氧基)-1,3-丁二烯 在 zinc(II) iodide 作用下， 以 苯 为溶剂， 反应 24.0h， 以65%的产率得到2-chloromethyl-2,3-dihydropyran-4-one
  参考文献：
  名称：

  Cycloaddition of 1-Methoxy-3-trimethylsilyloxybutadiene with Halogenated Carbonyl Compounds

  摘要：

  Cycloadditions of 1-methoxy-3-trimethylsilyloxy-1,3-butadiene (1) with halogenated carbonyl compounds (2) yielded corresponding substituted tetrahydro- and/or dihydropyran-4-ones (3 and/or 4). Lewis acids were found to be effective as catalysts. Reactions with less reactive carbonyl compounds (2c,d) afforded p-hydroxyacetophenone (5) produced by cyclodimerization of 1. Stereochemistry of the adducts was deduced by H-1 nmr spectroscopy.

  DOI：

  10.3987/com-90-5625

文献信息

• Cycloaddition of 1-Methoxy-3-trimethylsilyloxybutadiene with Halogenated Carbonyl Compounds
  作者：Akira Sera、Yasuji Iwasaki、Michio Umeda、Kuniaki Itoh

  DOI：10.3987/com-90-5625

  日期：——

  Cycloadditions of 1-methoxy-3-trimethylsilyloxy-1,3-butadiene (1) with halogenated carbonyl compounds (2) yielded corresponding substituted tetrahydro- and/or dihydropyran-4-ones (3 and/or 4). Lewis acids were found to be effective as catalysts. Reactions with less reactive carbonyl compounds (2c,d) afforded p-hydroxyacetophenone (5) produced by cyclodimerization of 1. Stereochemistry of the adducts was deduced by H-1 nmr spectroscopy.