4'-vinyl(1,1'-biphenyl)-3-amine | 1332747-49-5

• 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: 4'-vinyl(1,1'-biphenyl)-3-amine
• 英文别名: 3-(4-Ethenylphenyl)aniline
• CAS: 1332747-49-5
• 化学式: C₁₄H₁₃N
• 分子量: 195.264
• InChiKey: CJGAPXMGFUVQFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3-nitro-4'-vinylbiphenyl 在 glucose dehydrogenase 、 葡萄糖 、 nitroreductase from Bacillus tequilensis 、 还原型辅酶Ⅰ 作用下， 以 aq. phosphate buffer 、 二甲基亚砜 为溶剂， 以64%的产率得到4'-vinyl(1,1'-biphenyl)-3-amine
  参考文献：
  名称：

  Synthesis of Pharmaceutically Relevant Arylamines Enabled by a Nitroreductase from Bacillus tequilensis

  摘要：

  Arylamines are essential building blocks for the manufacture of valuable pharmaceuticals, pigments and dyes. However, their current industrial production involves the use of chemocatalytic procedures with a significant environmental impact. As a result, flavin‐dependent nitroreductases (NRs) have received increasing attention as sustainable catalysts for more ecofriendly synthesis of arylamines. In this study, we assessed a novel NR from Bacillus tequilensis, named BtNR, for the synthesis of pharmaceutically relevant arylamines, including valuable synthons used in the manufacture of blockbuster drugs such as vismodegib, sonidegib, linezolid and sildenafil. After optimizing the enzymatic reaction conditions, high conversion of nitroaromatics to arylamines (up to 97 %) and good product yields (up to 56 %) were achieved. Our results indicate that BtNR has a broad substrate scope, including bulky nitro benzenes, nitro pyrazoles and nitro pyridines. Hence, BtNR is an interesting biocatalyst for the synthesis of pharmaceutically relevant amine‐functionalized aromatics, providing an attractive alternative to traditional chemical synthesis methodologies.

  DOI：

  10.1002/cbic.202300846

文献信息

• Cobalt-Catalyzed Preparation of Arylindium Reagents from Aryl and Heteroaryl Bromides
  作者：Laksmikanta Adak、Naohiko Yoshikai

  DOI：10.1021/jo201174r

  日期：2011.9.16

  A cobalt–bathophenanthroline catalyst has been developed for the direct preparation of a variety of arylindium reagents from the corresponding aryl and heteroaryl bromides in the presence of indium metal and lithium chloride. The thus-formed arylindium reagents undergo efficient palladium-catalyzed cross-coupling reactions with aryl iodides, tolerating various functional groups including hydroxy and

  已经开发了钴-二苯菲咯啉钴催化剂，用于在铟金属和氯化锂存在下，由相应的芳基和杂芳基溴化物直接制备各种芳烃试剂。如此形成的芳基undergo试剂与芳基碘化物进行有效的钯催化交叉偶联反应，从而耐受包括羟基和游离氨基在内的各种官能团。
• US7723546B1
  申请人：——

  公开号：US7723546B1

  公开（公告）日：2010-05-25