1,3-bis(4-fluorophenyl)prop-2-ynyl methyl carbonate | 1191257-26-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 1,3-bis(4-fluorophenyl)prop-2-ynyl methyl carbonate
• CAS: 1191257-26-7
• 化学式: C₁₇H₁₂F₂O₃
• 分子量: 302.277
• InChiKey: RZLIZWFYCZUEBL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,3-bis(4-fluorophenyl)prop-2-ynyl methyl carbonate 、 benzyl (2-hydroxyphenyl)acetate 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 1,1'-bis(diphenylphosphino)ferrocene 作用下， 以 二甲基亚砜 为溶剂， 以66%的产率得到(3SR,4RS,Z)-benzyl 2-(4-fluorobenzylidene)-3-(4-fluorophenyl)chroman-4-carboxylate
  参考文献：
  名称：

  Stereoselective Construction of Substituted Chromans by Palladium-Catalyzed Cyclization of Propargylic Carbonates with 2-(2-Hydroxyphenyl)acetates

  摘要：

  Highly substituted chromans have been constructed in a highly stereoselective manner by a palladium-catalyzed reaction of propargylic carbonates with 2-(2-hydroxyphenyl)acetates. Enantioselective reactions also successfully proceeded to give the optically active chromans with high enantioselectivity.

  DOI：

  10.1021/ol901964z
• 作为产物：
  描述：

  1,3-bis(4-fluorophenyl)prop-2-yn-1-ol 、 氯甲酸甲酯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 以96%的产率得到1,3-bis(4-fluorophenyl)prop-2-ynyl methyl carbonate
  参考文献：
  名称：

  Stereoselective Construction of Substituted Chromans by Palladium-Catalyzed Cyclization of Propargylic Carbonates with 2-(2-Hydroxyphenyl)acetates

  摘要：

  Highly substituted chromans have been constructed in a highly stereoselective manner by a palladium-catalyzed reaction of propargylic carbonates with 2-(2-hydroxyphenyl)acetates. Enantioselective reactions also successfully proceeded to give the optically active chromans with high enantioselectivity.

  DOI：

  10.1021/ol901964z

文献信息

• Synthesis of Substituted Tetrahydrocyclobuta[<i>b</i>]benzofurans by Palladium-Catalyzed Substitution/[2+2] Cycloaddition of Propargylic Carbonates with 2-Vinylphenols
  作者：Masahiro Yoshida、Shoko Ohno、Kosuke Namba

  DOI：10.1002/anie.201306903

  日期：2013.12.16

  Radical methods: The title reaction proceeds in the presence of a palladium catalyst to deliver substituted tetrahydrocyclobuta[b]benzofurans in a stereoselective manner (see scheme). A radical mechanism is discussed.

  自由基方法：标题反应在钯催化剂的存在下进行，以立体选择性方式递送取代的四氢环丁[ b ]苯并呋喃（参见方案）。讨论了一种根本机制。