(3-bromo-3-(p-tolyl)prop-2-ene-1,1-diyl)dibenzene | 1160493-02-6

• 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: (3-bromo-3-(p-tolyl)prop-2-ene-1,1-diyl)dibenzene
• 英文别名: (E)-1-bromo-1-(p-tolyl)-3,3-diphenylprop-1-ene；1-[(E)-1-bromo-3,3-diphenylprop-1-enyl]-4-methylbenzene
• CAS: 1160493-02-6
• 化学式: C₂₂H₁₉Br
• 分子量: 363.297
• InChiKey: NEHUGVHPQQPVFI-CJLVFECKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  二苯甲醇 、 4-甲苯基乙炔 在 正丁基锂 、 溴化钛(IV) 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 0.67h， 以79%的产率得到(3-bromo-3-(p-tolyl)prop-2-ene-1,1-diyl)dibenzene
  参考文献：
  名称：

  Titanium(IV) Halide Mediated Coupling of Alkoxides and Alkynes: An Efficient and Stereoselective Route to Trisubstituted (E)-Alkenyl Halides

  摘要：

  Alkoxide C-O bond cleavage occurs readily at room temperature in the presence of titanium(IV) halide. Capture of the resultant carbocation by alkynes provides an efficient route to trisubstituted (E)-alkenyl halides with high stereoselectivity.

  DOI：

  10.1021/ol900669t

文献信息

• Microwave‐Assisted Condensation of Benzylic Alcohols and Alkynes Promoted by Zinc Halides: Concise Access to Alkenyl Halides
  作者：Poulomi Nandi、Komal Goel、Chinnabattigalla Sreenivasulu、Gedu Satyanarayana

  DOI：10.1002/ejoc.202100779

  日期：2021.9.14

  the synthesis of alkenyl halides are described under microwave-assisted conditions. The reaction proceeds through the condensation between sec-alcohols and terminal acetylenes and regeoselective hydro halogenation across the triple bond in the presence of simple and commercially available zinc halides. Three halide sources could successfully be employed to give a diverse range of alkenyl halide products

  在微波辅助条件下描述了一种简单的路易斯酸介导的烯基卤化物合成路线。该反应通过仲醇和末端乙炔之间的缩合以及在简单且市售的卤化锌存在下跨三键的区域选择性氢卤化进行。可以成功地使用三种卤化物源来产生各种不同的烯基卤化物产品以及茚和羰基产品。
• FeX₃-Promoted Intermolecular Addition of Benzylic Alcohols to Aromatic Alkynes: A Mild and Efficient Strategy for the Synthesis of Alkenyl Halides
  作者：Kai Ren、Min Wang、Lei Wang

  DOI：10.1002/ejoc.200901020

  日期：2010.1

  A convenient, effective, mild and simple strategy has been developed for the synthesis of alkenyl halides by the intermolecular addition of benzylic alcohols to aromatic alkynes. The reactions were carried out in the presence of iron(III) bromide or chloride in 1,2-dibromoethane without additives in air at room temperature. Alkenyl bromides and chlorides were obtained with high regio- and stereoselectivity

  已经开发了一种方便、有效、温和且简单的策略，用于通过苄醇与芳炔的分子间加成来合成卤代烯。反应在溴化铁（III）或氯化铁的 1,2-二溴乙烷中，在室温空气中进行，无添加剂。在温和的反应条件下，在 0.5-1 小时内以高到极好的收率获得了具有高区域和立体选择性（E/Z 高达 99:1）的烯基溴化物和氯化物。
• Titanium(IV) Halide Mediated Coupling of Alkoxides and Alkynes: An Efficient and Stereoselective Route to Trisubstituted (<i>E</i>)-Alkenyl Halides
  作者：Min-Liang Yao、Travis R. Quick、Zhongzhi Wu、Michael P. Quinn、George W. Kabalka

  DOI：10.1021/ol900669t

  日期：2009.6.18

  Alkoxide C-O bond cleavage occurs readily at room temperature in the presence of titanium(IV) halide. Capture of the resultant carbocation by alkynes provides an efficient route to trisubstituted (E)-alkenyl halides with high stereoselectivity.