3-Hydroxy-21-methyldocosa-4(E),15(E)-dien-1-yne | 129364-97-2

• 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: 3-Hydroxy-21-methyldocosa-4(E),15(E)-dien-1-yne
• 英文别名: (4E,15E)-21-methyldocosa-4,15-dien-1-yn-3-ol
• CAS: 129364-97-2；151329-64-5
• 化学式: C₂₃H₄₀O
• 分子量: 332.57
• InChiKey: SHZQEBVNRJHIDY-RVKYPOLFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  24
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-溴-5-甲基己烷 在 吡啶 、 盐酸 、 正丁基锂 、 氨 、 sodium 、 triphenylphosphine dibromide 1:1 addition complex 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 乙醚 、 二氯甲烷 、 氨 为溶剂， 反应 36.0h， 生成 3-Hydroxy-21-methyldocosa-4(E),15(E)-dien-1-yne
  参考文献：
  名称：

  Synthesis of some bioactive acetylenic alcohols, components of the marine sponge Cribrochalina vasculum

  摘要：

  Grignard coupling of isopropylmagnesium bromide with 4-(tetrahydropyranyloxy)bromobutane (2) and subsequent bromination gave 4. Alkylation of 1-(tetrahydropyranyloxy)undec-10-yne (5) with 4 and 1-bromohexane, acidic hydrolysis, and bromination furnished 7 and 9, respectively. Likewise, coupling of isobutylmagnesium bromide with 12-(tetrahydropyranyloxy)bromododecane (12) followed by bromination afforded 14. Alkylation of 1-(tetrahydropyranyloxy)-2-propyne (15) with 7, 9, and 14 and oxidation of the respective products afforded the alkynals 16a-c. These on reaction with lithium acetylide and subsequent chemoselective trans reduction of the internal alkynes led to the target compounds I-III.

  DOI：

  10.1021/jo00074a022

文献信息

• Synthesis of some bioactive acetylenic alcohols, components of the marine sponge Cribrochalina vasculum
  作者：B. A. Kulkarni、S. Chattopadhyay、A. Chattopadhyay、V. R. Mamdapur

  DOI：10.1021/jo00074a022

  日期：1993.10

  Grignard coupling of isopropylmagnesium bromide with 4-(tetrahydropyranyloxy)bromobutane (2) and subsequent bromination gave 4. Alkylation of 1-(tetrahydropyranyloxy)undec-10-yne (5) with 4 and 1-bromohexane, acidic hydrolysis, and bromination furnished 7 and 9, respectively. Likewise, coupling of isobutylmagnesium bromide with 12-(tetrahydropyranyloxy)bromododecane (12) followed by bromination afforded 14. Alkylation of 1-(tetrahydropyranyloxy)-2-propyne (15) with 7, 9, and 14 and oxidation of the respective products afforded the alkynals 16a-c. These on reaction with lithium acetylide and subsequent chemoselective trans reduction of the internal alkynes led to the target compounds I-III.