1-(2,2-dichloro-1-methoxypropoxy)-3-methylbut-2-ene | 1202934-74-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2,2-dichloro-1-methoxypropoxy)-3-methylbut-2-ene
• CAS: 1202934-74-4
• 化学式: C₉H₁₆Cl₂O₂
• 分子量: 227.131
• InChiKey: CCJBLJZDVDWCOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.14
• 重原子数：
  13.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-(2,2-dichloro-1-methoxypropoxy)-3-methylbut-2-ene 在 五甲基二乙烯三胺 、 copper(l) chloride 作用下， 以 乙腈 为溶剂， 反应 18.0h， 生成 、 、 、
  参考文献：
  名称：

  Atom transfer radical cyclization of O-allyl-2,2-dichlorohemiacetal acetates: an expedient method to dichloro-γ-lactones

  摘要：

  3-Alkyl-3-chloro-4-chloromethyl-gamma-lactones were synthesized in acceptable yields, exploiting the CuCl-N,N,N',N '',N ''-pentamethyldiethylenetriamine catalyzed atom transfer radical cyclization (ATRC) of O-allyl-2,2-dichlorohemiacetal acetates, starting materials easily prepared from 2,2-dichloroaldehydes. The oxidation of the intermediate dichloro-2-acetoxytetrahydrofurans was completed in a two-step, one-pot procedure: hydrolysis to gamma-lactol and final oxidation to lactone with Jones' reagent. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.10.053
• 作为产物：
  描述：

  甲醇 、 3-methyl-1-(1,2,2-trichloropropoxy)but-2-ene 在 lithium hydride 作用下， 以89%的产率得到1-(2,2-dichloro-1-methoxypropoxy)-3-methylbut-2-ene
  参考文献：
  名称：

  Atom transfer radical cyclization of O-allyl-2,2-dichlorohemiacetal acetates: an expedient method to dichloro-γ-lactones

  摘要：

  3-Alkyl-3-chloro-4-chloromethyl-gamma-lactones were synthesized in acceptable yields, exploiting the CuCl-N,N,N',N '',N ''-pentamethyldiethylenetriamine catalyzed atom transfer radical cyclization (ATRC) of O-allyl-2,2-dichlorohemiacetal acetates, starting materials easily prepared from 2,2-dichloroaldehydes. The oxidation of the intermediate dichloro-2-acetoxytetrahydrofurans was completed in a two-step, one-pot procedure: hydrolysis to gamma-lactol and final oxidation to lactone with Jones' reagent. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.10.053

文献信息

• Atom transfer radical cyclization of O-allyl-2,2-dichlorohemiacetal acetates: an expedient method to dichloro-γ-lactones
  作者：Franco Ghelfi、Fabrizio Roncaglia、Mariella Pattarozzi、Valerio Giangiordano、Giovanni Petrillo、Fernando Sancassan、Andrew F. Parsons

  DOI：10.1016/j.tet.2009.10.053

  日期：2009.12

  3-Alkyl-3-chloro-4-chloromethyl-gamma-lactones were synthesized in acceptable yields, exploiting the CuCl-N,N,N',N '',N ''-pentamethyldiethylenetriamine catalyzed atom transfer radical cyclization (ATRC) of O-allyl-2,2-dichlorohemiacetal acetates, starting materials easily prepared from 2,2-dichloroaldehydes. The oxidation of the intermediate dichloro-2-acetoxytetrahydrofurans was completed in a two-step, one-pot procedure: hydrolysis to gamma-lactol and final oxidation to lactone with Jones' reagent. (C) 2009 Elsevier Ltd. All rights reserved.