4-vinylideneoctan-1-ol | 1094489-61-8

• 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: 4-vinylideneoctan-1-ol
• 英文别名: 4-(n-butyl)-4,5-hexadienol
• CAS: 1094489-61-8
• 化学式: C₁₀H₁₈O
• 分子量: 154.252
• InChiKey: FZXNYNOUXSNFKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  11
• 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：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-vinylideneoctan-1-ol 在 碘 作用下， 以 正己烷 为溶剂， 反应 1.0h， 以84%的产率得到2-(n-butyl)-2-(1'-iodoethenyl)tetrahydrofuran
  参考文献：
  名称：

  Highly Regio- and Stereoselective Cyclic Iodoetherification of 4,5-Alkadienols. An Efficient Preparation of 2-(1′(Z)-Iodoalkenyl)tetrahydrofurans

  摘要：

  In this paper, an efficient way to synthesize 2-(1'(Z)-iodoalkenyl)tetrahydrofurans from 4,5-alkadienols and 12 was developed. The reaction of the 4,5-allenols with a substituent in the 3-position afforded the trans-2,3-disubstituted tetrahydrofurans with very high diastereoselectivity. However, when the axially optically active 4,5-allenol was treated with 12 in n-hexane, the efficiency for chirality transfer was low. This problem was circumvented by conducting the reaction in CH2Cl2 at room temperature and applying N-iodosuccinimide as the electrophilic reagent; however, the Z/E ratio for the products is much lower. Highly optically active Z-products may be prepared via the kinetic resolution via a Sonogashira coupling reaction with propargyl alcohol.

  DOI：

  10.1021/jo802079b
• 作为产物：
  描述：

  4-butylhexa-4,5-dienoic acid 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 2.0h， 以78%的产率得到4-vinylideneoctan-1-ol
  参考文献：
  名称：

  Highly Regio- and Stereoselective Cyclic Iodoetherification of 4,5-Alkadienols. An Efficient Preparation of 2-(1′(Z)-Iodoalkenyl)tetrahydrofurans

  摘要：

  In this paper, an efficient way to synthesize 2-(1'(Z)-iodoalkenyl)tetrahydrofurans from 4,5-alkadienols and 12 was developed. The reaction of the 4,5-allenols with a substituent in the 3-position afforded the trans-2,3-disubstituted tetrahydrofurans with very high diastereoselectivity. However, when the axially optically active 4,5-allenol was treated with 12 in n-hexane, the efficiency for chirality transfer was low. This problem was circumvented by conducting the reaction in CH2Cl2 at room temperature and applying N-iodosuccinimide as the electrophilic reagent; however, the Z/E ratio for the products is much lower. Highly optically active Z-products may be prepared via the kinetic resolution via a Sonogashira coupling reaction with propargyl alcohol.

  DOI：

  10.1021/jo802079b

文献信息

• Progress in Carbonylative [2+2+1] Cycloaddition: Utilization of a Nitrile Group as the π Component
  作者：Takashi Iwata、Fuyuhiko Inagaki、Chisato Mukai

  DOI：10.1002/anie.201305729

  日期：2013.10.11

  New tricks, old reactions: The treatment of 2‐(1,2‐propadienyl)phenylacetonitrile derivatives with a catalytic amount of [RhCl(CO)dppp}2] (dppp=1,3‐bis(diphenylphosphanyl)propane) under a CO atmosphere produced benzo[f]oxyindole derivatives (see scheme). This aza‐Pauson–Khand‐type reaction was applicable to aliphatic substrates, thus resulting in the formation of the azabicyclo[3.3.0]octadienone derivatives

  新的技巧，旧的反应：在催化条件下处理催化量为[RhCl（CO）dppp} 2 ]（dppp = 1,3-‐双（二苯基膦基）丙烷的2-（1,2-丙二烯基）苯基乙腈衍生物CO气氛下生成苯并[ f ]氧基吲哚衍生物（参见方案）。该aza-Pauson-Khand型反应适用于脂肪族底物，从而导致形成azabicyclo [3.3.0] octadienone衍生物。