2-[(5-Chloro-2-methoxyphenyl)methyl]oxirane | 1026729-13-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-[(5-Chloro-2-methoxyphenyl)methyl]oxirane
• 英文别名: 2-[(5-chloro-2-methoxyphenyl)methyl]oxirane
• CAS: 1026729-13-4
• 化学式: C₁₀H₁₁ClO₂
• 分子量: 198.649
• InChiKey: MAPIZVITFSAQIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  21.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-[(5-Chloro-2-methoxyphenyl)methyl]oxirane 、 methyl 3-acetoxy-3-(4-chlorophenyl)-2-methylenepropanoate 在 硫酸 作用下， 以 四氢呋喃 为溶剂， 以57%的产率得到(3E)-3-(4-chlorobenzylidene)-5-(5-chloro-2-methoxybenzyl)tetrahydro-2H-pyran-2-one
  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

• Fe(III) chloride catalyzed conversion of epoxides to acetonides
  作者：Sumit Saha、Samir Kumar Mandal、Subhas Chandra Roy

  DOI：10.1016/j.tetlet.2008.07.147

  日期：2008.10

  A mild and efficient method for the preparation of acetonides from epoxides catalyzed by iron(III) chlorides has been developed.

  已经开发了一种温和而有效的方法，用于从氯化铁（III）催化的环氧化物制备乙炔化物。
• 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.