2,2-dichloro-1-(2-propenyloxy)pentyl acetate | 1202934-54-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,2-dichloro-1-(2-propenyloxy)pentyl acetate
• 英文别名: (2,2-Dichloro-1-prop-2-enoxypentyl) acetate
• CAS: 1202934-54-0
• 化学式: C₁₀H₁₆Cl₂O₃
• 分子量: 255.141
• InChiKey: SYFNBRBAUWLHMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,2-dichloro-1-(2-propenyloxy)pentyl acetate 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 β-trans-2-acetoxy-3-chloro-4-chloromethyl-3-propyltetrahydrofuran 、 α-cis-2-acetoxy-3-chloro-4-chloromethyl-3-propyltetrahydrofuran 、 α-trans-2-acetoxy-3-chloro-4-chloromethyl-3-propyltetrahydrofuran 、 β-cis-2-acetoxy-3-chloro-4-chloromethyl-3-propyltetrahydrofuran
  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：

  2,2-二氯戊醛 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 2,2-dichloro-1-(2-propenyloxy)pentyl acetate
  参考文献：
  名称：

  Acetic Anhydride/Et₃N/DMAP: An Effective Acetylating System for Hemiacetals

  摘要：

  [image omitted] The selective and efficient acetylation of the hemiacetal hydroxyl in the equilibrium mixture between RCl2C(OAll)OH and AllOH/RCl2CHO was achieved using the acylating system Ac2O/Et3N/dimethylaminopyridine (DMAP).

  DOI：

  10.1080/00397911003797882

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.
• Acetic Anhydride/Et₃N/DMAP: An Effective Acetylating System for Hemiacetals
  作者：Fabrizio Roncaglia、Andrew F. Parsons、Franco Bellesia、Franco Ghelfi

  DOI：10.1080/00397911003797882

  日期：2011.3.28

  [image omitted] The selective and efficient acetylation of the hemiacetal hydroxyl in the equilibrium mixture between RCl2C(OAll)OH and AllOH/RCl2CHO was achieved using the acylating system Ac2O/Et3N/dimethylaminopyridine (DMAP).