4-butyl-6-ethylocta-4,5-dienoic acid | 1094489-36-7

• 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-butyl-6-ethylocta-4,5-dienoic acid
• CAS: 1094489-36-7
• 化学式: C₁₄H₂₄O₂
• 分子量: 224.343
• InChiKey: DLDFYOVQIPFPAA-UHFFFAOYSA-N

反应信息

• 作为反应物：
  描述：

  4-butyl-6-ethylocta-4,5-dienoic acid 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 3.3h， 以93%的产率得到4-butyl-6-ethylocta-4,5-dienol
  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-butyl-6-ethylocta-4,5-dienenitrile 在 sodium hydroxide 、 水 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 3.2h， 以86%的产率得到4-butyl-6-ethylocta-4,5-dienoic acid
  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