(2Z,8E,10E)-heptadeca-2,8,10-triene-4,6-diyn-1-ol | 111128-29-1

• 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: (2Z,8E,10E)-heptadeca-2,8,10-triene-4,6-diyn-1-ol
• 英文别名: (2Z,8E,10E)-heptadeca-2,8,10-trien-4,6-diyn-1-ol
• CAS: 111128-29-1
• 化学式: C₁₇H₂₂O
• 分子量: 242.361
• InChiKey: MNRSGFGJPZSJIX-ZVHWMEOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.41
• 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：

  (Z)-5-(trimethylsilyl)pent-2-en-4-yn-1-ol 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 四丁基氟化铵 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 生成 (2Z,8E,10E)-heptadeca-2,8,10-triene-4,6-diyn-1-ol
  参考文献：
  名称：

  Metal-catalyzed coupling reactions on an olefin template: the total synthesis of Bupleurynol

  摘要：

  The naturally occurring polyacetylene Bupleurynol was synthesized in a convergent and stereospecific manner using a series of metal-mediated cross-coupling reactions. The synthesis demonstrates the utility of using a di-functional olefin template for the stereospecific synthesis of a disubstituted alkene product and its elaboration to a natural product target. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01753-2

文献信息

• Use of Olefin Templates in Queued Chemical Transformations Using Late Transition Metal Catalysis. Total Synthesis of <i>cis</i> and <i>trans </i>Bupleurynol via a Single Multireaction Sequence
  作者：Haleh Ghasemi、Luis M. Antunes、Michael G. Organ

  DOI：10.1021/ol0489853

  日期：2004.8.1

  1-Bromo-2-iodoethylene (9) was used as a central, pseudosymmetric building block for the fully convergent and modular synthesis of two related natural products, cis (1a) and trans (1b) bupleurynol. In doing so, a 9-step synthesis of 1a (reported previously) has been vastly truncated to one single operation by using queued cross-coupling reactions with Pd catalysis, negating the need for any protecting

  1-溴-2-碘乙烯（9）被用作中央，假对称的构建基块，用于完全收敛和模块化合成两种相关的天然产物，顺式（1a）和反式（1b）丁香酚。这样做，通过使用具有Pd催化作用的排队交叉偶联反应，已将1a的9步合成（先前报道）大大缩短为一个操作，从而消除了对任何保护基化学反应的需要。
• Metal-catalyzed coupling reactions on an olefin template: the total synthesis of Bupleurynol
  作者：Luis M. Antunes、Michael G. Organ

  DOI：10.1016/s0040-4039(03)01753-2

  日期：2003.9

  The naturally occurring polyacetylene Bupleurynol was synthesized in a convergent and stereospecific manner using a series of metal-mediated cross-coupling reactions. The synthesis demonstrates the utility of using a di-functional olefin template for the stereospecific synthesis of a disubstituted alkene product and its elaboration to a natural product target. (C) 2003 Elsevier Ltd. All rights reserved.