(E)-1-bromo-2-(phenylethenyl)-4-methylbenzene | 99398-20-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E)-1-bromo-2-(phenylethenyl)-4-methylbenzene
• 英文别名: (E)-1-bromo-4-methyl-2-styrylbenzene；1-bromo-4-methyl-2-[(E)-2-phenylethenyl]benzene
• CAS: 99398-20-6
• 化学式: C₁₅H₁₃Br
• 分子量: 273.172
• InChiKey: DMCKWWSOCWTGIL-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.93
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  (E)-1-bromo-2-(phenylethenyl)-4-methylbenzene 在 溴 、 potassium tert-butylate 作用下， 以 二氯甲烷 、 叔丁醇 为溶剂， 反应 8.0h， 以28%的产率得到1-bromo-4-methyl-2-(phenylethynyl)benzene
  参考文献：
  名称：

  The First Aryne Evolution from the Reactions of Selenonium Salts with Aryllithiums

  摘要：

  The first example of the benzyne generation was found in the reactions of alkynylselenonium salt 1a with 1.0 equiv. of phenyllithium in THF at room temperature for 3 h. The formation of the aryne intermediate was confirmed in the reactions of alkynylselenonium salt 1b and tri-p-tolylselenonium salt 6b with tolyllithium, which gave a mixture of alkynylbiphenyl derivatives 18 and 19 in 19% yield (18:19=11:8) and a mixture of bitolyls 28 and 29 in 63% yield (28:29=2:1), respectively. The reaction mechanisms of these reactions are discussed. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)01090-x
• 作为产物：
  描述：

  2-溴-5-甲苯甲醛 、 苯基膦酸二乙酯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以74%的产率得到(E)-1-bromo-2-(phenylethenyl)-4-methylbenzene
  参考文献：
  名称：

  通过铁 (III) 催化的羰基-烯烃复分解反应制备多环芳烃

  摘要：

  多环芳烃是有机化学、药物化学和材料科学中的重要结构基序。基于铁(III)催化的羰基-烯烃复分解反应的设计原理描述了这些化合物的新合成策略的开发。该方法的特点是操作简单、官能团兼容性高和区域选择性，同时依赖 FeCl3 作为环境友好、地球丰富的金属催化剂。已经获得了氧杂环丁烷作为催化羰基-烯烃闭环复分解反应中间体的实验证据。

  DOI：

  10.1021/jacs.7b01114

文献信息

• Gold(I) Carbenes by Retro-Buchner Reaction: Generation and Fate
  作者：Yahui Wang、Paul R. McGonigal、Bart Herlé、Maria Besora、Antonio M. Echavarren

  DOI：10.1021/ja411626v

  日期：2014.1.15

  The fate of the aryl gold(I) carbenes generated by retro-Buchner reaction of ortho-substituted 7-aryl-1,3,5-cycloheptatrienes is dependent on the constitution of the ortho substituent. Indenes and fluorenes are obtained by intramolecular reaction of highly electrophilic gold(I) carbenes with alkenes and arenes. According to density functional theory calculations, the gold-catalyzed retro-Buchner process

  由邻位取代的 7-芳基-1,3,5-环庚三烯的逆布氏反应生成的芳基金 (I) 卡宾的命运取决于邻位取代基的构成。茚和芴是通过高亲电性金 (I) 卡宾与烯烃和芳烃的分子内反应获得的。根据密度泛函理论计算，金催化的逆布氏过程逐步发生，尽管两个碳-碳裂解发生在相当平坦的势能表面上。
• OLSEN, R. J.;PRUETT, S. R., J. ORG. CHEM., 1985, 50, N 26, 5457-5460
  作者：OLSEN, R. J.、PRUETT, S. R.

  DOI：——

  日期：——
• 10.1021/acs.orglett.4c01145
  作者：Wang, Xuelan、Zhong, Jiaoyue、Luo, Meiming、Zeng, Xiaoming

  DOI：10.1021/acs.orglett.4c01145

  日期：——
• Polycyclic Aromatic Hydrocarbons via Iron(III)-Catalyzed Carbonyl–Olefin Metathesis
  作者：Christopher C. McAtee、Paul S. Riehl、Corinna S. Schindler

  DOI：10.1021/jacs.7b01114

  日期：2017.3.1

  Polycyclic aromatic hydrocarbons are important structural motifs in organic chemistry, pharmaceutical chemistry, and materials science. The development of a new synthetic strategy toward these compounds is described based on the design principle of iron(III)-catalyzed carbonyl-olefin metathesis reactions. This approach is characterized by its operational simplicity, high functional group compatibility

  多环芳烃是有机化学、药物化学和材料科学中的重要结构基序。基于铁(III)催化的羰基-烯烃复分解反应的设计原理描述了这些化合物的新合成策略的开发。该方法的特点是操作简单、官能团兼容性高和区域选择性，同时依赖 FeCl3 作为环境友好、地球丰富的金属催化剂。已经获得了氧杂环丁烷作为催化羰基-烯烃闭环复分解反应中间体的实验证据。
• The First Aryne Evolution from the Reactions of Selenonium Salts with Aryllithiums
  作者：Shin-ichi Watanabe、Keiichirou Yamamoto、Yukiko Itagaki、Tatsunori Iwamura、Tetsuo Iwama、Tadashi Kataoka

  DOI：10.1016/s0040-4020(99)01090-x

  日期：2000.2

  The first example of the benzyne generation was found in the reactions of alkynylselenonium salt 1a with 1.0 equiv. of phenyllithium in THF at room temperature for 3 h. The formation of the aryne intermediate was confirmed in the reactions of alkynylselenonium salt 1b and tri-p-tolylselenonium salt 6b with tolyllithium, which gave a mixture of alkynylbiphenyl derivatives 18 and 19 in 19% yield (18:19=11:8) and a mixture of bitolyls 28 and 29 in 63% yield (28:29=2:1), respectively. The reaction mechanisms of these reactions are discussed. (C) 2000 Elsevier Science Ltd. All rights reserved.