2,5-dicarbomethoxy-1,6-diphenyl-1,5-hexadiene

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 2,5-dicarbomethoxy-1,6-diphenyl-1,5-hexadiene
• 英文别名: 2,5-dibenzylidenehexanedioic acid dimethyl ester；dimethyl 2,5-di((E)-benzylidene)hexanedioate；dimethyl (2E,5E)-2,5-dibenzylidenehexanedioate
• 化学式: C₂₂H₂₂O₄
• 分子量: 350.414
• InChiKey: WMSITADSAOJESF-MXWIWYRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  methyl 2-(bromomethyl)-3-phenylacrylate 在 氢气 、 三乙胺 、 1,4-双(二苯基膦)丁烷 、 palladium dichloride 作用下， 以 N-甲基吡咯烷酮 、 正己烷 为溶剂， 20.0~80.0 ℃ 、101.33 kPa 条件下， 反应 22.0h， 生成 2,5-dicarbomethoxy-1,6-diphenyl-1,5-hexadiene
  参考文献：
  名称：

  钯催化的烯丙胺或烯丙醇与H 2作为唯一还原剂的烯丙基-烯丙基还原偶联

  摘要：

  基于还原偶联的催化碳-碳键形成是制备有机化合物的有力方法。鉴定环境无害的还原剂是建立有效的还原偶联反应的关键。本文描述了一种有效的策略，该策略使H 2成为钯催化的烯丙基-烯丙基还原偶联反应的唯一还原剂。各种各样的烯丙胺和烯丙基醇以及烯丙基醚可以在1 atm大气压的H 2下顺利进行C-C偶联产物的输送。动力学研究表明，双核钯物质参与了催化循环。

  DOI：

  10.1021/acs.orglett.0c03865

文献信息

• Metallic Samarium Promoted Self-Coupling of Baylis-Hillman Adducts to Functionalized 1,5-Hexadienes in the Presence of the I2/ClCO2Et/BiCl3 System
  作者：Xueshun Jia、Haishan Bian、Jian Li、Chunju Li、Gan Wang、Zheng Duan

  DOI：10.1055/s-0029-1219808

  日期：2010.6

  A facile strategy for the self-coupling of Baylis-Hillman adducts to functionalized 1,5-hexadienes has been described. Promoted by the Sm/I2/ClCO2Et/BiCl3 system, the present method allows for the conversion of MBH adducts to their corresponding 1,5-hexadienes.

  报道了一种对Baylis-Hillman加合物与功能化1,5-己二烯进行自耦合的简便策略。该方法在Sm/I2/ClCO2Et/BiCl3体系促进下，实现了MBH加合物向相应1,5-己二烯的转化。
• Metal-Mediated Reactions of α-Bromomethyl-Propenoate Esters
  作者：S. E. Drewes、R. B. Taylor、N. S. Ramesar、J. S. Field

  DOI：10.1080/00397919508011363

  日期：1995.2

  Methyl-2-bromomethylprop-2-enoate reacts with benzaldehyde and with salicylaldehyde via its Sn and Zn complexes under aqueous conditions to form alpha-methylene-gamma-lactones in high yields. In the case of salicylaldehyde X-ray analysis proves conclusively formation of a five- rather than a seven-membered ring. Under the above conditions 2-bromomethyl-3-phenylprop-2-enoate does not afford any cyclic products.
• SmI2-mediated elimination reaction of Baylis–Hillman adducts controlled by temperature: a facile synthesis of trisubstituted alkenes and 1,5-hexadiene derivatives with E-stereoselectivity
  作者：Jian Li、Weixing Qian、Yongmin Zhang

  DOI：10.1016/j.tet.2004.04.087

  日期：2004.6

  Promoted by samarium diiodide, the Baylis-Hillman adducts undergo hydroxyl elimination to form trisubstituted alkenes with total (E)-stereoselectivity in good to excellent yields. The flexibility of this method also opens a new route to synthesize a class of 1,5-hexadiene derivatives by temperature tuning. (C) 2004 Elsevier Ltd. All rights reserved.
• Palladium-Catalyzed Allyl–Allyl Reductive Coupling of Allylamines or Allylic Alcohols with H₂ as Sole Reductant
  作者：Xibing Zhou、Guoying Zhang、Renbin Huang、Hanmin Huang

  DOI：10.1021/acs.orglett.0c03865

  日期：2021.1.15

  building on reductive coupling is a powerful method for the preparation of organic compounds. The identification of environmentally benign reductants is key for establishing an efficient reductive coupling reaction. Herein an efficient strategy enabling H2 as the sole reductant for the palladium-catalyzed allyl–allyl reductive coupling reaction is described. A wide range of allylamines and allylic alcohols

  基于还原偶联的催化碳-碳键形成是制备有机化合物的有力方法。鉴定环境无害的还原剂是建立有效的还原偶联反应的关键。本文描述了一种有效的策略，该策略使H 2成为钯催化的烯丙基-烯丙基还原偶联反应的唯一还原剂。各种各样的烯丙胺和烯丙基醇以及烯丙基醚可以在1 atm大气压的H 2下顺利进行C-C偶联产物的输送。动力学研究表明，双核钯物质参与了催化循环。