methyl 2'-bromo[1,1-biphenyl]-3-carboxylate | 207508-66-5

• 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: methyl 2'-bromo[1,1-biphenyl]-3-carboxylate
• 英文别名: Methyl 3-(2-bromophenyl)benzoate
• CAS: 207508-66-5
• 化学式: C₁₄H₁₁BrO₂
• 分子量: 291.144
• InChiKey: DLISJHMZFPTSDY-UHFFFAOYSA-N

物化性质

• 沸点：
  381.2±25.0 °C(Predicted)
• 密度：
  1.394±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  氰化钾 、 methyl 2'-bromo[1,1-biphenyl]-3-carboxylate 在 四(三苯基膦)钯 氰化锌 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以98%的产率得到2-氰基-[1,1-联苯]-3-羧酸甲酯
  参考文献：
  名称：

  o-Bromophenylzinc compound: a readily available and efficient synthetic equivalent of o-phenylene 1-anion 2-cation

  摘要：

  An o-bromophenylzinc compound, first prepared in an excellent yield by the reaction of o-bromoiodobenzene with zinc powder in THF, was found to be an efficient synthetic equivalent of o-phenylene 1-anion 2-cation in Pd(O)-catalyzed stepwise cross-coupling reactions, affording unsymmetrically 12-disubstituted benzenes with diverse substitution patterns and with a variety of functional groups. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00443-2
• 作为产物：
  描述：

  3-碘苯甲酸甲酯 、 o-bromophenylzinc iodide 在 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以94%的产率得到methyl 2'-bromo[1,1-biphenyl]-3-carboxylate
  参考文献：
  名称：

  o-Bromophenylzinc compound: a readily available and efficient synthetic equivalent of o-phenylene 1-anion 2-cation

  摘要：

  An o-bromophenylzinc compound, first prepared in an excellent yield by the reaction of o-bromoiodobenzene with zinc powder in THF, was found to be an efficient synthetic equivalent of o-phenylene 1-anion 2-cation in Pd(O)-catalyzed stepwise cross-coupling reactions, affording unsymmetrically 12-disubstituted benzenes with diverse substitution patterns and with a variety of functional groups. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00443-2

文献信息

• Through the Maze: Cross-Coupling Pathways to a Helical Hexaphenyl “Geländer” Molecule
  作者：Michel Rickhaus、Linda Maria Bannwart、Oliver Unke、Heiko Gsellinger、Daniel Häussinger、Marcel Mayor

  DOI：10.1002/ejoc.201403322

  日期：2015.2

  highlights a new concept on how to induce chirality in a hexaphenyl GelA¤nder-type system. Bridging a terphenyl backbone with a considerably longer benzyl ether oligomer enforces a continuous twist of the molecule, while preventing an achiral meso form. By highlighting cross-coupling strategies and explored synthetic pathways, this report aims to serve as an Ariadne`s thread for the synthesis of precisely

  本文重点介绍了如何在六苯基 GelA?nder 型系统中诱导手性的新概念。用相当长的苄基醚低聚物桥接三联苯骨架可以强制分子的连续扭曲，同时防止非手性内消旋形式。通过突出交叉偶联策略和探索的合成途径，本报告旨在作为 Ariadne 的线索，用于合成精确功能化的复杂多环芳烃系统。概述了访问设计目标所需的综合挑战和注意事项，并提出了组装每个步骤的解决方案。遇到的异构化与合成工具一样被讨论，以获取具有多正交部分的高度官能化的中间体。
• o-Bromophenylzinc compound: a readily available and efficient synthetic equivalent of o-phenylene 1-anion 2-cation
  作者：Masateru Okano、Masayuki Amano、Kentaro Takagi

  DOI：10.1016/s0040-4039(98)00443-2

  日期：1998.5

  An o-bromophenylzinc compound, first prepared in an excellent yield by the reaction of o-bromoiodobenzene with zinc powder in THF, was found to be an efficient synthetic equivalent of o-phenylene 1-anion 2-cation in Pd(O)-catalyzed stepwise cross-coupling reactions, affording unsymmetrically 12-disubstituted benzenes with diverse substitution patterns and with a variety of functional groups. (C) 1998 Elsevier Science Ltd. All rights reserved.