6-ethoxy-3-phenyl-3-en-1-yne | 1181658-80-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-ethoxy-3-phenyl-3-en-1-yne
• 英文别名: (E)-(6-ethoxyhex-3-en-1-yn-3-yl)benzene；[(E)-6-ethoxyhex-3-en-1-yn-3-yl]benzene
• CAS: 1181658-80-9
• 化学式: C₁₄H₁₆O
• 分子量: 200.28
• InChiKey: HCRRUEGAIJUYOE-ACCUITESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  乙醇 、 cyclopropyl phenyl propargyl alcohol 在 ferrocenium hexafluorophosphate 作用下， 以 二氯甲烷 为溶剂， 反应 1.25h， 以73%的产率得到6-ethoxy-3-phenyl-3-en-1-yne
  参考文献：
  名称：

  二茂铁阳离子作为环丙基取代的丙炔醇醚化的催化剂：乙炔的形成和机理的见解

  摘要：

  二茂铁或二茂铁硼酸阳离子（Fc +）利用醇亲核试剂催化炔丙基取代反应。用环丙基取代基进行重排，生成相应的烯炔。噻吩基取代基未观察到环丙基开环。建议反应的离子机理。

  DOI：

  10.1002/ejoc.201901330

文献信息

• Highly Efficient Synthesis of Tri- and Tetrasubstituted Conjugated Enynes from Brønsted Acid Catalyzed Alkoxylation of 1-Cyclopropylprop-2-yn-1-ols with Alcohols
  作者：Srinivasa Reddy Mothe、Philip Wai Hong Chan

  DOI：10.1021/jo9008244

  日期：2009.8.21

  A highly efficient triflic acid catalyzed ring opening of a wide variety of 1-cyclopropyl-2-propyn-1-ols with alcohols as an efficient synthetic route to conjugated enynes is reported herein. The reaction was operationally straight forward and accomplished in good to excellent yields (44-100%,), high product turnovers (up to 10,000), and with complete regioselectivity under mild conditions with a low catalyst loading of 0.01 mol%. The mechanism is suggested to involve protonation of the alcohol substrate by the TfOH catalyst, followed by ionization of the starting material. This causes ring opening, of the cyclopropane moiety and trapping by the alcohol nucleophile to give the conjugated enyne product. The synthetic utility Of the present method was also exemplified by the efficient large-scale Conversion in grain quantities of one example studied in this work to the corresponding conjugated enyne product in excellent yield and turnover number.
• Ferrocenium Cations as Catalysts for the Etherification of Cyclopropyl-Substituted Propargylic Alcohols: Ene-yne Formation and Mechanistic Insights
  作者：Deva Saroja Talasila、Matthew J. Queensen、Michael Barnes-Flaspoler、Kellsie Jurkowski、Evan Stephenson、Jordan M. Rabus、Eike B. Bauer

  DOI：10.1002/ejoc.201901330

  日期：2019.11.30

  Ferrocenium or ferrocenium boronic acid cations (Fc+) catalyze propargylic substitution reactions utilizing alcohol nucleophiles. Rearrangement to the corresponding ene‐ynes takes place with a cyclopropyl substituent. No cyclopropyl ring‐opening is observed with a thienyl substituent. An ionic mechanism is suggested for the reactions.

  二茂铁或二茂铁硼酸阳离子（Fc +）利用醇亲核试剂催化炔丙基取代反应。用环丙基取代基进行重排，生成相应的烯炔。噻吩基取代基未观察到环丙基开环。建议反应的离子机理。