(3E)-3-苄基-5-(氯甲基)四氢-2H-吡喃-2-酮 | 1026729-51-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 中文名称: (3E)-3-苄基-5-(氯甲基)四氢-2H-吡喃-2-酮
• 英文名称: (3E)-3-benzylidene-5-(chloromethyl)tetrahydro-2H-pyran-2-one
• 英文别名: (3E)-3-benzylidene-5-(chloromethyl)oxan-2-one
• CAS: 1026729-51-0
• 化学式: C₁₃H₁₃ClO₂
• 分子量: 236.698
• InChiKey: WUADEMHBLFEHKY-WUXMJOGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  2-[乙酰氧基(苯基)甲基]丙烯酸甲酯 、 环氧氯丙烷 在 硫酸 作用下， 以 四氢呋喃 为溶剂， 以53%的产率得到(3E)-3-苄基-5-(氯甲基)四氢-2H-吡喃-2-酮
  参考文献：
  名称：

  Titanocene(III) Chloride Mediated Radical-Induced Addition to Baylis−Hillman Adducts: Synthesis of (E)- and (Z)-Trisubstituted Alkenes and α-Methylene/Arylidene δ-Lactones

  摘要：

  Baylis-Hillman adduct underwent smooth radical-induced condensation with activated bromo compounds and epoxides using titanocene(III) chloride (CP2TiCl) as the radical generator. The reactions of activated bromo compounds with 3-acetoxy-2-methylene alkanoates provided (E)-alkenes exclusively, whereas similar reactions with 3-acetoxy-2-methylenealkanenitriles led to (Z)-alkenes as the major product. The reactions of epoxides with Baylis-Hillman adduct furnished alpha-methylene/arylidene-delta-lactones in good yield via addition followed by in situ lactonization.

  DOI：

  10.1021/jo800049p

文献信息

• Titanocene(III) Chloride Mediated Radical-Induced Addition to Baylis−Hillman Adducts: Synthesis of (<i>E</i>)- and (<i>Z</i>)-Trisubstituted Alkenes and α-Methylene/Arylidene δ-Lactones
  作者：Samir K. Mandal、Moumita Paira、Subhas C. Roy

  DOI：10.1021/jo800049p

  日期：2008.5.1

  Baylis-Hillman adduct underwent smooth radical-induced condensation with activated bromo compounds and epoxides using titanocene(III) chloride (CP2TiCl) as the radical generator. The reactions of activated bromo compounds with 3-acetoxy-2-methylene alkanoates provided (E)-alkenes exclusively, whereas similar reactions with 3-acetoxy-2-methylenealkanenitriles led to (Z)-alkenes as the major product. The reactions of epoxides with Baylis-Hillman adduct furnished alpha-methylene/arylidene-delta-lactones in good yield via addition followed by in situ lactonization.