1-pentyl-2-propenyl dichloroacetate | 937036-44-7

• 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: 1-pentyl-2-propenyl dichloroacetate
• 英文别名: Oct-1-en-3-yl 2,2-dichloroacetate；oct-1-en-3-yl 2,2-dichloroacetate
• CAS: 937036-44-7
• 化学式: C₁₀H₁₆Cl₂O₂
• 分子量: 239.142
• InChiKey: ARHPDCWZVVZUMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  14
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-pentyl-2-propenyl dichloroacetate 在 novozyme 435 作用下， 以 乙二醇二甲醚 为溶剂， 反应 24.0h， 生成 1-pentyl-2-propenyl dichloroacetate 、 (S)-(+)-1-辛烯-3-醇 、 (R)-(-)-1-辛烯-3-醇
  参考文献：
  名称：

  Atom transfer radical cyclization (ATRC) applied to a chemoenzymatic synthesis of Quercus lactones

  摘要：

  The natural fragrances (+)-trans whisky lactone 2 and (+)-trans cognac lactone 4, together with a minor amount of their (-)cis stereoisomers, were prepared in 50% and 42% overall yield, respectively, starting from racemic 1-hepten-3-ol (+/-)-5 and 1-octen-3-ol (+/-)-6. The procedure involved first the enantioconvergent, lipase mediated transformation of the secondary allylic alcohols derived dichloroacetates (+/-)-7 and (+/-)-8 into the corresponding homochiral (+)-7 and (+)-8, combined with their cyclization under a transition metal catalyzed atom transfer process. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.02.012
• 作为产物：
  描述：

  正己醛 在 4-二甲氨基吡啶 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 1-pentyl-2-propenyl dichloroacetate
  参考文献：
  名称：

  Atom transfer radical cyclization (ATRC) applied to a chemoenzymatic synthesis of Quercus lactones

  摘要：

  The natural fragrances (+)-trans whisky lactone 2 and (+)-trans cognac lactone 4, together with a minor amount of their (-)cis stereoisomers, were prepared in 50% and 42% overall yield, respectively, starting from racemic 1-hepten-3-ol (+/-)-5 and 1-octen-3-ol (+/-)-6. The procedure involved first the enantioconvergent, lipase mediated transformation of the secondary allylic alcohols derived dichloroacetates (+/-)-7 and (+/-)-8 into the corresponding homochiral (+)-7 and (+)-8, combined with their cyclization under a transition metal catalyzed atom transfer process. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.02.012

文献信息

• Atom transfer radical cyclization (ATRC) applied to a chemoenzymatic synthesis of Quercus lactones
  作者：Fulvia Felluga、Cristina Forzato、Franco Ghelfi、Patrizia Nitti、Giuliana Pitacco、Ugo Maria Pagnoni、Fabrizio Roncaglia

  DOI：10.1016/j.tetasy.2007.02.012

  日期：2007.3

  The natural fragrances (+)-trans whisky lactone 2 and (+)-trans cognac lactone 4, together with a minor amount of their (-)cis stereoisomers, were prepared in 50% and 42% overall yield, respectively, starting from racemic 1-hepten-3-ol (+/-)-5 and 1-octen-3-ol (+/-)-6. The procedure involved first the enantioconvergent, lipase mediated transformation of the secondary allylic alcohols derived dichloroacetates (+/-)-7 and (+/-)-8 into the corresponding homochiral (+)-7 and (+)-8, combined with their cyclization under a transition metal catalyzed atom transfer process. (c) 2007 Elsevier Ltd. All rights reserved.