(2Z,5E)-octa-2,5-dien-1-ol | 292821-75-1

• 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,5E)-octa-2,5-dien-1-ol
• CAS: 292821-75-1
• 化学式: C₈H₁₄O
• 分子量: 126.199
• InChiKey: INXWZSVGTHMNEU-FDTUMDBZSA-N

物化性质

• 沸点：
  201.4±19.0 °C(Predicted)
• 密度：
  0.868±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  (2Z,5E)-octa-2,5-dien-1-ol 在 吡啶 、 喹啉 、 甲基氯化镁 、 三溴化磷 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 7.0h， 生成 2-((E)-10-vinyl-pentadec-12-en-8-ynyloxy)-tetrahydro-pyran
  参考文献：
  名称：

  Large-scale preparation of (9Z,12E)-[1-13C]-octadeca-9,12-dienoic acid, (9Z,12Z,15E)-[1-13C]-octadeca-9,12,15-trienoic acid and their [1-13C] all-cis isomers

  摘要：

  Several grams of labelled trans linoleic and linolenic acids with high chemical and isomeric purities (> 97%) have been prepared for human metabolism studies. A total of 12.5 g of (9Z,12E)-[1-C-13]-octadeca-9,12-dienoic acid and 6.3 g of (9Z,12Z,15E)-[1-C-13]-octadeca-9,12,15-trienoic acid were obtained in, respectively: seven steps (7.8% overall yield) and 11 steps (7% overall yield) from 7-bromo-heptan-1-ol. The trans bromo precursors used for the labelling were synthesised by using copper-catalysed couplings. The trans fatty acids were then obtained via the nitrile derivatives. A total of 23.5 g of (9Z,12Z)-[1-C-13]-octadeca-9,12-dienoic acid and 10.4 g of (9Z,12Z,15Z)-[1-C-13]-octadeca-9,12,15-trienoic acid were prepared in five steps in, respectively, 32 and 18% overall yield. Large quantities of bromo and chloro precursors were synthesised from the commercially available acid according to Barton's procedure. In all cases, the main impurities ( > 0.5%) of each labelled fatty acid have been characterised. (C) 2000 Elsevier Science Ireland Ltd. All rights reserved.

  DOI：

  10.1016/s0009-3084(00)00137-7
• 作为产物：
  描述：

  1-溴-2-戊烯 在 bis(acetylacetonate)nickel(II) 、 sodium tetrahydroborate 、 甲基溴化镁 、 氢气 、 乙二胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 5.5h， 生成 (2Z,5E)-octa-2,5-dien-1-ol
  参考文献：
  名称：

  (-)-Deschloromytilipin A和(-)-Danicalipin A的催化对映选择性二卤化和选择性合成

  摘要：

  描述了简单烯丙醇的钛基催化对映选择性二氯化。这种二氯化反应提供了对用于合成氯硫脂天然产物的所有常见二氯醇构建块的立体选择性访问。执行对映选择性合成 ent-(-)-deschloromytilipin A 和简洁的八步合成 ent-(-)-danicalipin A，并采用二氯化反应作为第一步。报道了该系统扩展到对映选择性二溴化及其在合成与溴硫脂相关的五溴化物立体阵列中的用途。所描述的二氯化和二溴化反应能够在复杂的环境中进行非对映控制，允许对多卤化立体六联体的天然和非天然非对映异构体进行 X 射线晶体结构分析。

  DOI：

  10.1021/jacs.6b01643

文献信息

• Large-scale preparation of (9Z,12E)-[1-13C]-octadeca-9,12-dienoic acid, (9Z,12Z,15E)-[1-13C]-octadeca-9,12,15-trienoic acid and their [1-13C] all-cis isomers
  作者：O Loreau、A Maret、D Poullain、J.M Chardigny、J.L Sébédio、B Beaufrère、J.P Noël

  DOI：10.1016/s0009-3084(00)00137-7

  日期：2000.6

  Several grams of labelled trans linoleic and linolenic acids with high chemical and isomeric purities (> 97%) have been prepared for human metabolism studies. A total of 12.5 g of (9Z,12E)-[1-C-13]-octadeca-9,12-dienoic acid and 6.3 g of (9Z,12Z,15E)-[1-C-13]-octadeca-9,12,15-trienoic acid were obtained in, respectively: seven steps (7.8% overall yield) and 11 steps (7% overall yield) from 7-bromo-heptan-1-ol. The trans bromo precursors used for the labelling were synthesised by using copper-catalysed couplings. The trans fatty acids were then obtained via the nitrile derivatives. A total of 23.5 g of (9Z,12Z)-[1-C-13]-octadeca-9,12-dienoic acid and 10.4 g of (9Z,12Z,15Z)-[1-C-13]-octadeca-9,12,15-trienoic acid were prepared in five steps in, respectively, 32 and 18% overall yield. Large quantities of bromo and chloro precursors were synthesised from the commercially available acid according to Barton's procedure. In all cases, the main impurities ( > 0.5%) of each labelled fatty acid have been characterised. (C) 2000 Elsevier Science Ireland Ltd. All rights reserved.
• Catalytic Enantioselective Dihalogenation and the Selective Synthesis of (−)-Deschloromytilipin A and (−)-Danicalipin A
  作者：Matthew L. Landry、Dennis X. Hu、Grace M. McKenna、Noah Z. Burns

  DOI：10.1021/jacs.6b01643

  日期：2016.4.20

  A titanium-based catalytic enantioselective dichlorination of simple allylic alcohols is described. This dichlorination reaction provides stereoselective access to all common dichloroalcohol building blocks used in syntheses of chlorosulfolipid natural products. An enantioselective synthesis of ent-(-)-deschloromytilipin A and a concise, eight-step synthesis of ent-(-)-danicalipin A are executed and

  描述了简单烯丙醇的钛基催化对映选择性二氯化。这种二氯化反应提供了对用于合成氯硫脂天然产物的所有常见二氯醇构建块的立体选择性访问。执行对映选择性合成 ent-(-)-deschloromytilipin A 和简洁的八步合成 ent-(-)-danicalipin A，并采用二氯化反应作为第一步。报道了该系统扩展到对映选择性二溴化及其在合成与溴硫脂相关的五溴化物立体阵列中的用途。所描述的二氯化和二溴化反应能够在复杂的环境中进行非对映控制，允许对多卤化立体六联体的天然和非天然非对映异构体进行 X 射线晶体结构分析。