undec-5-yn-1-en-4-yl formate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: undec-5-yn-1-en-4-yl formate
• 英文别名: Undec-1-en-5-yn-4-yl formate
• 化学式: C₁₂H₁₈O₂
• 分子量: 194.274
• InChiKey: KMKBCCVTCVBJNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-甲基甲酰胺 、 2-辛醛 、 3-溴丙烯 在 indium 作用下， 反应 72.0h， 以63%的产率得到undec-5-yn-1-en-4-yl formate
  参考文献：
  名称：

  Control of Skeletal Connectivity in Indium Promoted Reactions:  1,2-Additions and Cope Rearrangements En Route to Lactol Formation

  摘要：

  Indium promoted coupling reactions between propargyl aldehydes (3) and allyl halides under aqueous and organic conditions are reported. Coupling reactions under aqueous conditions occur via 1,2-addition with excellent yields to afford 4-hydroxy-1-ene-5-ynes (8). Coupling reactions under organic conditions also add in a 1,2-fashion, but the initial products can be induced to undergo oxy-Cope rearrangements giving 2,5-hexadienals (9). Oxy-Cope rearrangement of 8 followed by a secondary addition step under highly basic conditions leads to lactol formation (10) in good to excellent yields. This paper reveals the versatility and control of product formation which may be attained when working with propargyl aldehyde (3) and allyl halide systems under indium promoted coupling conditions.

  DOI：

  10.1021/jo070020k

文献信息

• Control of Skeletal Connectivity in Indium Promoted Reactions:  1,2-Additions and Cope Rearrangements En Route to Lactol Formation
  作者：Thomas Mitzel、Joe Wzorek、Annie Troutman、Kristen Allegue

  DOI：10.1021/jo070020k

  日期：2007.4.1

  Indium promoted coupling reactions between propargyl aldehydes (3) and allyl halides under aqueous and organic conditions are reported. Coupling reactions under aqueous conditions occur via 1,2-addition with excellent yields to afford 4-hydroxy-1-ene-5-ynes (8). Coupling reactions under organic conditions also add in a 1,2-fashion, but the initial products can be induced to undergo oxy-Cope rearrangements giving 2,5-hexadienals (9). Oxy-Cope rearrangement of 8 followed by a secondary addition step under highly basic conditions leads to lactol formation (10) in good to excellent yields. This paper reveals the versatility and control of product formation which may be attained when working with propargyl aldehyde (3) and allyl halide systems under indium promoted coupling conditions.