ethyl 7-hydroxyhept-2-ynoate

• 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-hydroxyhept-2-ynoate
• 英文别名: ethyl 7-hydroxy-2-heptynoate
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: QXSWHALLAUXQOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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-hydroxyhept-2-ynoate 、 异氰基乙酸乙酯 在 1,3-双(二苯基膦)丙烷 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以59%的产率得到2,3-di(ethoxycarbonyl)-4-(4-hydroxybutyl)pyrrole
  参考文献：
  名称：

  Phosphine-catalyzed regioselective heteroaromatization between activated alkynes and isocyanides leading to pyrroles

  摘要：

  The organophosphine catalyzed reaction of activated alkynes with isocyanides produces the corresponding heteroaromatization products, pyrroles, regioselectively in good yields. The reaction proceeds most probably through the 1,4-addition of the nucleophilic phosphine catalyst to the alkynes, followed by a [3+2] cycloaddition between the resulting alkenyl phosphine intermediates and a carbanion derived from the isocyanides. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.02.104
• 作为产物：
  描述：

  6-(叔-丁基二甲基硅烷基氧基)-1-己炔 在 正丁基锂 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.5h， 生成 ethyl 7-hydroxyhept-2-ynoate
  参考文献：
  名称：

  非钯过渡金属催化的氢化锡：Bu 3 SnF / PMHS作为氢化锡源

  摘要：

  研究了使用原位生成的Bu 3 SnH进行的钼，钴，镍，钌和铑催化的炔烃氢化。在大多数情况下，卜3的SnF +聚甲基（PMHS）执行以及卜的原位源3 SNH。相比之下，Bu 3 SnCl / KF aq / PMHS的组合在Pd催化的氢化锡锡反应中获得了较早的成功，但在这些金属介导的炔烃锡锡锡氢化反应中使用较少。

  DOI：

  10.1016/j.tet.2013.02.064

文献信息

• Catalytic Aerobic Synthesis of Aromatic Ethers from Non-Aromatic Precursors
  作者：Marc-Olivier Simon、Simon A. Girard、Chao-Jun Li

  DOI：10.1002/anie.201200698

  日期：2012.7.23

  Only little waste: Aryl ether formation is accomplished by oxidative condensation of alcohols and 2‐cyclohexenones. The reaction complements the existing methods used by synthetic chemists to obtain aryl ethers, and allows a straightforward access to a wide range of functionalized products. In addition, the catalytic reaction with O2 as the oxidant generates water as the only by‐product and provides

  只有很少的浪费：芳基醚的形成是通过醇和2-环己烯酮的氧化缩合完成的。该反应是合成化学家用于获得芳基醚的现有方法的补充，并允许直接获得各种功能化的产物。此外，以O 2为氧化剂的催化反应生成水作为唯一的副产物，并为芳基醚提供了“更绿色”的方法。
• 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)
• Phosphine-Catalyzed Enantioselective Synthesis of Oxygen Heterocycles
  作者：Ying Kit Chung、Gregory C. Fu

  DOI：10.1002/anie.200805377

  日期：2009.3.9

  phosphepine 1 catalyzes the transformation of an array of hydroxy‐2‐alkynoates into saturated oxygen heterocycles with good enantioselectivity. Phenols are also shown to participate in such phosphine‐catalyzed cyclizations, including an asymmetric variant. This method provides a new approach to the enantioselective synthesis of tetrahydrofurans, tetrahydropyrans, and dihydrobenzopyrans.

  手性膦 1催化一系列羟基-2-炔酸酯转化为具有良好对映选择性的饱和氧杂环。苯酚也被证明参与这种膦催化的环化反应，包括不对称变体。该方法为四氢呋喃、四氢吡喃和二氢苯并吡喃的对映选择性合成提供了一种新方法。
• Copper- or Phosphine-Catalyzed Reaction of Alkynes with Isocyanides. Regioselective Synthesis of Substituted Pyrroles Controlled by the Catalyst
  作者：Shin Kamijo、Chikashi Kanazawa、Yoshinori Yamamoto

  DOI：10.1021/ja051875m

  日期：2005.6.1

  The copper-catalyzed reaction of isocyanides (CNCH(2)EWG(1)) 1 with electron-deficient alkynes (RC equivalent to CEWG(2)) 2 gave the 2,4-di-EWG-substituted pyrroles 3 selectively, whereas the phosphine-catalyzed reaction of 1 with 2 afforded the 2,3-di-EWG-subsituted pyrroles 4. Accordingly, regioselective synthesis of substituted pyrroles has been achieved by merely choosing the catalyst.
• 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.