1-bromo-2-(2-methyl-2-phenylethenyl)benzene | 904744-73-6

• 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: 1-bromo-2-(2-methyl-2-phenylethenyl)benzene
• 英文别名: 1-bromo-2-(2-phenylprop-1-enyl)benzene
• CAS: 904744-73-6
• 化学式: C₁₅H₁₃Br
• 分子量: 273.172
• InChiKey: VTBLJLRCWGYUJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.01
• 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：

  1-bromo-2-(2-methyl-2-phenylethenyl)benzene 在 chromium dichloride 、 烯丙基溴化镁 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 以49 %的产率得到Alpha－甲基均二苯乙烯
  参考文献：
  名称：

  Cr-Catalyzed Intramolecular Arylative Cross-Coupling of Unactivated C–H Bonds with C–Halide Bonds

  摘要：

  DOI：

  10.1021/acs.orglett.4c01145
• 作为产物：
  描述：

  (1-Phenylethyl)triphenylphosphoniumiodid 、 邻溴苯甲醛 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 32.0h， 以86%的产率得到1-bromo-2-(2-methyl-2-phenylethenyl)benzene
  参考文献：
  名称：

  Metal-Catalyzed Cycloisomerization of Enyne Functionalities via a 1,3-Alkylidene Migration

  摘要：

  We report a new metal-catalyzed 6-endo-dig cyclization of cis-4,6-dien-1-yn-3-ols, which produces substituted benzene and naphthalene derivatives with structural reorganization. In this process, we observe a 1,3-alkylidene migration via cleavage of the olefin double bond of the starting substrates. The ease and reliability of this cyclization are manifested by its compatibility with a wide array of diverse substrates and several pi-alkyne activators, including PtCl2, Zn(OTf)2, AuCl, and AuCl3.

  DOI：

  10.1021/ja062515h

文献信息

• A Visible-Light-Mediated Oxidative CN Bond Formation/Aromatization Cascade: Photocatalytic Preparation of N-Arylindoles
  作者：Soumitra Maity、Nan Zheng

  DOI：10.1002/anie.201205137

  日期：2012.9.17

  Just add light and air: Structurally diverse N‐arylindoles can be prepared from readily prepared o‐styryl anilines through visible‐light photocatalysis. The reaction, which is conducted open to air, is mediated by [Ru(bpz)3](PF6)2 (bpz=2,2′‐bipyrazine) and involves both CN bond formation and aromatization (see scheme). Using suitably substituted substrates, a 1,2‐carbon shift can be also incorporated

  只需添加光和空气：可以通过可见光光催化从容易制备的邻苯乙烯基苯胺制备结构多样的N-芳基吲哚。该反应在空气中进行，由 [Ru(bpz) 3 ](PF 6 ) 2 (bpz=2,2′-联吡嗪)介导，涉及 C  N 键形成和芳构化（见方案）。使用适当取代的底物，1,2-碳转移也可以纳入该级联反应中。
• Munro, David P.; Sharp, John T., Journal of the Chemical Society. Perkin transactions I, 1984, # 4, p. 849 - 858
  作者：Munro, David P.、Sharp, John T.

  DOI：——

  日期：——
• Cleavage of the Inert C(sp²)–Ar σ-Bond of Alkenes by a Spatial Constrained Interaction with Phosphinidene
  作者：Junjian Wang、Donghui Wei、Zheng Duan、François Mathey

  DOI：10.1021/jacs.0c11195

  日期：2020.12.16

  [1 + 2] cycloaddition is a classical reaction between the electrophilic phosphinidene and an alkene. However, a spatial constraint blocks this well-known reaction and enables an unprecedented chemoselective C(sp2)-Ar σ-bond insertion of the alkene. The theoretical calculations demonstrate that this C-C bond cleavage is energetically feasible and thermodynamically favored through an electrophilic rearrangement and concomitant 1,9-aryl migration without involving any strained intermediate.