5-propyl-3,4-octadienol | 1094489-00-5

• 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: 5-propyl-3,4-octadienol
• CAS: 1094489-00-5
• 化学式: C₁₁H₂₀O
• 分子量: 168.279
• InChiKey: MASJQHMCDKXFGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 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：

  5-propyl-3,4-octadienol 在 甲醇 、 ruthenium trichloride 、 sodium periodate 、 1,10-菲罗啉 、 亚碘酰苯 、 硫酸 、 silver trifluoromethanesulfonate 、 potassium carbonate 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 0.08h， 生成
  参考文献：
  名称：

  Aminodiols via Stereocontrolled Oxidation of Methyleneaziridines

  摘要：

  A highly diastereoselective Ru-catalyzed oxidation/reduction sequence of bicyclic methyleneaziridines provides a facile route to complex 1-amino-2,3-diol motifs. The relative anti stereochemistry between the amine and the vicinal alcohol are proposed to result from 1,3-bischelation in the transition state by the C1 and C3 heteroatoms.

  DOI：

  10.1021/ol5003576
• 作为产物：
  描述：

  ethyl 5-propylocta-3,4-dienoate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 2.7h， 以0.3591 g的产率得到5-propyl-3,4-octadienol
  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

• Aminodiols via Stereocontrolled Oxidation of Methyleneaziridines
  作者：Jared W. Rigoli、Ilia A. Guzei、Jennifer M. Schomaker

  DOI：10.1021/ol5003576

  日期：2014.3.21

  A highly diastereoselective Ru-catalyzed oxidation/reduction sequence of bicyclic methyleneaziridines provides a facile route to complex 1-amino-2,3-diol motifs. The relative anti stereochemistry between the amine and the vicinal alcohol are proposed to result from 1,3-bischelation in the transition state by the C1 and C3 heteroatoms.
• Highly Regio- and Stereoselective Cyclic Iodoetherification of 4,5-Alkadienols. An Efficient Preparation of 2-(1′(<i>Z</i>)-Iodoalkenyl)tetrahydrofurans
  作者：Bo Lü、Xinpeng Jiang、Chunling Fu、Shengming Ma

  DOI：10.1021/jo802079b

  日期：2009.1.2

  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.