(E)-oct-5-en-2-yn-1-ol | 101339-87-1

• 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: (E)-oct-5-en-2-yn-1-ol
• CAS: 101339-87-1
• 化学式: C₈H₁₂O
• 分子量: 124.183
• InChiKey: RVVAQBVGICRZSA-ONEGZZNKSA-N

物化性质

• 沸点：
  183.7±15.0 °C(Predicted)
• 密度：
  0.919±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.34
• 重原子数：
  9.0
• 可旋转键数：
  2.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  (E)-oct-5-en-2-yn-1-ol 生成 (2E,5E)-octa-2,5-dien-1-ol
  参考文献：
  名称：

  KOBAYASI, AKIO;KUBOTA, KIKUEHDA;IVAMOTO, MAKOTO;TAMURA, XIROSI;KOGAMI, KU+

  摘要：

  DOI：
• 作为产物：
  描述：

  反-2-戊烯-1-醇 在 吡啶 、 异丙基氯化镁 、 二溴三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 7.5h， 生成 (E)-oct-5-en-2-yn-1-ol
  参考文献：
  名称：

  Proof-of-principle direct double cyclisation of a linear C₁₅-precursor to a dibrominated bicyclic medium-ring ether relevant toLaurenciaspecies

  摘要：

  与Laurencia物种相关的双环介质环醚通过直接双溴化环化合成得到。

  DOI：

  10.1039/c4cc06402j

文献信息

• 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。
• A Unifying Stereochemical Analysis for the Formation of Halogenated C₁₅-Acetogenin Medium-Ring Ethers From <i>Laurencia</i> Species via Intramolecular Bromonium Ion Assisted Epoxide Ring-Opening and Experimental Corroboration with a Model Epoxide
  作者：Karl J. Bonney、D. Christopher Braddock

  DOI：10.1021/jo301580c

  日期：2012.11.2

  unifying stereochemical analysis for the formation of the constitutional isomeric halogenated C15-acetogenin medium-ring ether natural products from Laurencia species is presented, where an intramolecular bromonium ion assisted epoxide ring-opening reaction of enantiomerically pure epoxides can account for ring-size, the position of the halogen substituents, and relative and absolute configurations of

  提出了一种统一的立体化学分析方法，用于分析由Laurencia种构成的结构异构异构卤代C 15-产乙酸原的中环醚天然产物，其中对映体纯的环氧化物的分子内溴离子辅助的环氧化物开环反应可解释环的大小，卤素取代基的位置，以及已知天然产物的相对和绝对构型。实验上，模型环氧化物证实了该方法同时形成7环，8环和9环醚的可行性，该醚对应于来自Laurencia物种的已知代​​谢物的卤代中环醚。
• 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.