2,19-heneicosadiyn-11-ol | 307324-15-8

• 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: 2,19-heneicosadiyn-11-ol
• 英文别名: henicosa-2,19-diyn-11-ol
• CAS: 307324-15-8
• 化学式: C₂₁H₃₆O
• 分子量: 304.516
• InChiKey: HHLUEVMKSZXXJX-UHFFFAOYSA-N

物化性质

• 沸点：
  417.5±30.0 °C(Predicted)
• 密度：
  0.896±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.86
• 重原子数：
  22.0
• 可旋转键数：
  14.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2,19-heneicosadiyn-11-ol 在 Tris(t-butoxy)(2,2-dimethylpropylidyne)tungsten(VI), 98% Schrock Alkyne Metathesis Catalyst 、 重铬酸吡啶 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 16.5h， 生成 cycloheptadec-9-yn-1-one
  参考文献：
  名称：

  Ring closing alkyne metathesis: stereoselective synthesis of civetone

  摘要：

  A concise and stereoselective synthesis of the macrocyclic musk civetone 6 is reported starting from readily available 9-undecynol. The key steps comprise a ring closing metathesis of diyne 4 followed by Lindlar reduction of the resulting cycloalkyne 5. The cyclization can be effected either by using catalytic amounts of the Schrock alkylidyne complex (t-BuO)(3)W drop CCMe3 or by means of an in situ catalyst mixture generated from Mo(CO)(6) and p-trifluoromethylphenol. Both catalyst systems turned out to be compatible with the unprotected ketone function of the substrate. (C) 2000 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-328x(00)00096-6
• 作为产物：
  描述：

  9-undecynal 、 8-decynylmagnesium bromide 以 四氢呋喃 为溶剂， 反应 10.0h， 以58%的产率得到2,19-heneicosadiyn-11-ol
  参考文献：
  名称：

  Ring closing alkyne metathesis: stereoselective synthesis of civetone

  摘要：

  A concise and stereoselective synthesis of the macrocyclic musk civetone 6 is reported starting from readily available 9-undecynol. The key steps comprise a ring closing metathesis of diyne 4 followed by Lindlar reduction of the resulting cycloalkyne 5. The cyclization can be effected either by using catalytic amounts of the Schrock alkylidyne complex (t-BuO)(3)W drop CCMe3 or by means of an in situ catalyst mixture generated from Mo(CO)(6) and p-trifluoromethylphenol. Both catalyst systems turned out to be compatible with the unprotected ketone function of the substrate. (C) 2000 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-328x(00)00096-6