Eicosa-2,13-diyn-1-ol | 151329-57-6

• 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: Eicosa-2,13-diyn-1-ol
• 英文别名: Icosa-2,13-diyn-1-ol；icosa-2,13-diyn-1-ol
• CAS: 151329-57-6
• 化学式: C₂₀H₃₄O
• 分子量: 290.489
• InChiKey: JIYPLYCTQVYHBL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  21
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  Eicosa-2,13-diyn-1-ol 在 氨 、 sodium 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 氨 为溶剂， 生成 (+/-)-(4E,15E)-Docosa-4,15-dien-1-yn-3-ol
  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
• 作为产物：
  描述：

  11-(四氢-2H-吡喃-2-基氧基)-1-十一碳炔 在 吡啶 、 盐酸 、 正丁基锂 、 triphenylphosphine dibromide 1:1 addition complex 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 六甲基磷酰三胺 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 Eicosa-2,13-diyn-1-ol
  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.