ethyl 7-hydroxynon-8-en-2-ynoate | 1160164-08-8

• 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: ethyl 7-hydroxynon-8-en-2-ynoate
• 英文别名: ethyl 7-hydroxy-7-vinylhept-2-ynoate
• CAS: 1160164-08-8
• 化学式: C₁₁H₁₆O₃
• 分子量: 196.246
• InChiKey: FXQWMBFGFTZJND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 7-hydroxynon-8-en-2-ynoate 在 lithium hexamethyldisilazane 作用下， 反应 1.0h， 以44%的产率得到3-环辛烯-1-羧酸,8-羰基-,乙基酯
  参考文献：
  名称：

  Facile access to cyclooctanoid ring systems via microwave-assisted tandem 6-exo dig cyclization–rearrangement sequence

  摘要：

  Appropriately substituted 5-alkyn-1-ol systems bearing a nitrile moiety at the triple bond serve as versatile precursors to a variety of cyclooctenone derivatives via a "one-pot" base-catalyzed oxyanionic 6-exo dig cyclization/Claisen rearrangement sequence under microwave irradiation. It was found that the initially formed cyclic intermediate consists of a mixture of endo and exocyclic isomers, which appear to be in equilibrium under the reaction conditions. However, the only observed products from these reactions are α-cyano substituted cyclooctenones, derived from the exocyclic dihydrofuran intermediates.

  DOI：

  10.1016/j.tet.2014.02.089
• 作为产物：
  描述：

  6-三甲基硅烷基-己-5-炔-1-醇 在 4-二甲氨基吡啶 、 正丁基锂 、 4-甲基苯磺酸吡啶 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 1.5h， 生成 ethyl 7-hydroxynon-8-en-2-ynoate
  参考文献：
  名称：

  Facile access to cyclooctanoid ring systems via microwave-assisted tandem 6-exo dig cyclization–rearrangement sequence

  摘要：

  Appropriately substituted 5-alkyn-1-ol systems bearing a nitrile moiety at the triple bond serve as versatile precursors to a variety of cyclooctenone derivatives via a "one-pot" base-catalyzed oxyanionic 6-exo dig cyclization/Claisen rearrangement sequence under microwave irradiation. It was found that the initially formed cyclic intermediate consists of a mixture of endo and exocyclic isomers, which appear to be in equilibrium under the reaction conditions. However, the only observed products from these reactions are α-cyano substituted cyclooctenones, derived from the exocyclic dihydrofuran intermediates.

  DOI：

  10.1016/j.tet.2014.02.089

文献信息

• AuCl ₃ ‐Catalyzed Hydroalkoxylation of Conjugated Alkynoates: Synthesis of Five‐ and Six‐Membered Cyclic Acetals
  作者：Alejandro Diéguez‐Vázquez、C. Christoph Tzschucke、José Crecente‐Campo、Sally McGrath、Steven V. Ley

  DOI：10.1002/ejoc.200801221

  日期：2009.4

  offers a convenient route for the synthesis of six-membered cyclic acetals, which are common substructures of polyketide natural products. When conjugated 6-hydroxyhexynoates are used as starting materials, either five-membered cyclic E-enol ethers or the corresponding acetals can be obtained by simply choosing the appropriate reaction solvent. NMR spectroscopic studies were carried out to determine the

  AuCl3 催化的共轭 7-羟基庚酸酯的双加氢烷氧基化为合成六元环缩醛提供了一条方便的途径，六元环缩醛是聚酮化合物天然产物的常见亚结构。当以共轭6-羟基己炔酸酯为原料时，只需选择合适的反应溶剂，即可得到五元环E-烯醇醚或相应的缩醛。进行核磁共振光谱研究以确定后多米诺 5-外环化 - 加氢烷氧基化反应的动力学和途径。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• TBAF-catalyzed cyclization of 6-hydroxyhex-2-ynoates and 7-hydroxyhept-2-ynoates
  作者：Xiao Qing Wang、Ping Jing Jia、Su Ping Liu、Wei Yu

  DOI：10.1016/j.cclet.2011.01.023

  日期：2011.8

  Tetrabutyl ammonium fluoride (TBAF) was found to be capable of catalyzing the intramolecular hydroalkoxylation of 6-hydroxyhex-2-ynoates and 7-hydroxyhept-2-ynoates. The reaction could be used to prepare 2,5-substituted THF rings and 2,6-substituted THP rings. (C) 2011 Wei Yu. Published by Elsevier BY, on behalf of Chinese Chemical Society. All rights reserved.