2,2-dichloro-1-(3-methyl-2-butenyloxy)propyl acetate | 916137-87-6

• 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-(3-methyl-2-butenyloxy)propyl acetate
• 英文别名: [2,2-Dichloro-1-(3-methylbut-2-enoxy)propyl] acetate
• CAS: 916137-87-6
• 化学式: C₁₀H₁₆Cl₂O₃
• 分子量: 255.141
• InChiKey: YHYYILOPRVHDSD-UHFFFAOYSA-N

物化性质

• 沸点：
  94-96 °C(Press: 4 Torr)
• 密度：
  1.159±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  6
• 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-(3-methyl-2-butenyloxy)propyl 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-cis-2-acetoxy-3-chloro-4-[(1-chloro-1-methyl)ethyl]-3-methyltetrahydrofuran 、 α-cis-2-acetoxy-3-chloro-4-[(1-chloro-1-methyl)ethyl]-3-methyltetrahydrofuran 、 α-trans-2-acetoxy-3-chloro-4-[(1-chloro-1-methyl)ethyl]-3-methyltetrahydrofuran 、 β-trans-2-acetoxy-3-chloro-4-[(1-chloro-1-methyl)ethyl]-3-methyltetrahydrofuran
  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：

  异戊烯醇 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 21.0h， 生成 2,2-dichloro-1-(3-methyl-2-butenyloxy)propyl acetate
  参考文献：
  名称：

  A new and effective route to (±)-botryodiplodin and (±)-epi-botryodiplodin acetates using a halogen atom transfer Ueno–Stork cyclization

  摘要：

  (±)-Botryodiplodin 和 (±)-epi-botryodiplodin 的醋酸酯在良好产率下通过一个实际的四步路线制备。该方法在构建战略性的四氢呋喃环时，基于前所未有的卤素原子转移 Ueno-Stork 环化反应，涉及 O-烯丙基α,α-二卤半缩醛醋酸酯，该反应由 CuCl/N,N,N',N'',N''-五甲基二乙三胺的氧化还原复合物催化。(c) 2006 Elsevier Ltd. 保留所有权利。

  DOI：

  10.1016/j.tetlet.2006.08.121

文献信息

• 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).
• 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.
• A new and effective route to (±)-botryodiplodin and (±)-epi-botryodiplodin acetates using a halogen atom transfer Ueno–Stork cyclization
  作者：Laurent De Buyck、Cristina Forzato、Franco Ghelfi、Adele Mucci、Patrizia Nitti、Ugo M. Pagnoni、Andrew F. Parsons、Giuliana Pitacco、Fabrizio Roncaglia

  DOI：10.1016/j.tetlet.2006.08.121

  日期：2006.10

  (+/-)-Botryodiplodin and (+/-)-epi-botryodiplodin acetates were prepared in good yields following a practical four step route. The method, for the construction of the strategic tetrahydrofuran ring, hinged on an unprecedented halogen atom transfer Ueno-Stork cyclization of an O-allyl alpha,alpha-dihalohemiacetal acetate, catalyzed by the redox complex CuCl/N,N,N ',N '',N ''-pentamethyldiethylenetriamine. (c) 2006 Elsevier Ltd. All rights reserved.

  (±)-Botryodiplodin 和 (±)-epi-botryodiplodin 的醋酸酯在良好产率下通过一个实际的四步路线制备。该方法在构建战略性的四氢呋喃环时，基于前所未有的卤素原子转移 Ueno-Stork 环化反应，涉及 O-烯丙基α,α-二卤半缩醛醋酸酯，该反应由 CuCl/N,N,N',N'',N''-五甲基二乙三胺的氧化还原复合物催化。(c) 2006 Elsevier Ltd. 保留所有权利。