3-nitro-4'-vinylbiphenyl | 1345691-21-5

• 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: 3-nitro-4'-vinylbiphenyl
• 英文别名: 3-nitro-4′-vinylbiphenyl；3-nitro-4’-vinylbiphenyl；1-(4-Ethenylphenyl)-3-nitrobenzene；1-(4-ethenylphenyl)-3-nitrobenzene
• CAS: 1345691-21-5
• 化学式: C₁₄H₁₁NO₂
• 分子量: 225.247
• InChiKey: SIQRSFLFZWKZOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  17
• 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：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  1-碘-3-硝基苯 、 4-乙烯基苯硼酸 在 T406石油添加剂 、 palladium diacetate 、 potassium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 以92%的产率得到3-nitro-4'-vinylbiphenyl
  参考文献：
  名称：

  Jha, Rajeev Ranjan; Chaudhary, Ritu; Chandra, Ramesh, Journal of the Indian Chemical Society, 2011, vol. 88, # 8, p. 1187 - 1194

  摘要：

  DOI：

文献信息

• Benzotriazol-1-ylmethanol: An excellent bidentate ligand for the copper/palladium-catalyzed C-N and C-C coupling reaction
  作者：Rajeev R. Jha、Jaspal Singh、Rakesh K. Tiwari、Akhilesh K. Verma

  DOI：10.3998/ark.5550190.0014.219

  日期：——

  benzotriazole based N,O bidentate liga nds for the Cu-catalyzed N-arylation of πexcessive nitrogen heterocycles is described. This ligand accomplishes C-N coupling of Nheterocycles and C-C coupling of boronic acids with a variety of hindered, functionalized aryl/heteroaryl halides under mild reaction conditi ons in good to excellent yields. Using his ligand C-N and C-C (Suzuki) couplings with bromoarenes

  描述了一种有效的基于苯并三唑的 N,O 双齿配体，用于铜催化的 π 过量氮杂环的 N-芳基化。该配体在温和的反应条件下以良好至极好的产率完成了杂环的 CN 偶联和硼酸与各种受阻的官能化芳基/杂芳基卤化物的 CC 偶联。使用他的配体 CN 和 CC (Suzuki) 与溴芳烃偶联可以在较少的催化剂负载下进行。一系列失活和受阻的芳基卤化物可以干净地反应，以高产率提供功能化的联芳基衍生物。
• 2-(1-Benzotriazolyl)pyridine: A Robust Bidentate Ligand for the Palladium-Catalyzed CC (Suzuki, Heck, Fujiwara-Moritani, Sonogashira), CN and CS Coupling Reactions
  作者：Akhilesh K. Verma、Rajeev R. Jha、Ritu Chaudhary、Rakesh K. Tiwari、Abhinandan K. Danodia

  DOI：10.1002/adsc.201200583

  日期：2013.2.1

  designed and employed for the palladium-catalyzed CC (Suzuki, Heck, Fujiwara–Moritani, and Sonogashira), CN and CS coupling reactions. The ligand was found to be inexpensive, thermally stable, easy to synthesize from easily accessible starting materials on a multigram scale, show simplicity in use, and robustness in application, making this ligand effective for different coupling reactions. Suitably, the

  设计了一种新型的双齿配体1-（吡啶-2-基）-1 H-苯并[ d ] [1,2,3]三唑，并用于钯催化的CC（Suzuki，Heck，Fujiwara– Moritani和Sonogashira），CN和CS偶联反应。发现该配体便宜，热稳定，易于以几克规模由容易获得的起始原料合成，显示出使用简单性和在应用中的坚固性，从而使该配体对于不同的偶联反应有效。适当地，苯并三唑环的NN键的供体能力和吡啶环的N上的孤对电子增强了配体的二齿能力。
• Olefin cross-metathesis/Suzuki–Miyaura reactions on vinylphenylboronic acid pinacol esters
  作者：Christine B. Baltus、Irina S. Chuckowree、Neil J. Press、Iain J. Day、Simon J. Coles、Graham J. Tizzard、John Spencer

  DOI：10.1016/j.tetlet.2012.12.081

  日期：2013.3

  A series of alkenyl phenylboronic acid pinacol esters has been synthesized via an olefin cross-metathesis reaction of vinylphenylboronic acid pinacol ester derivatives. After catalytic hydrogenation, the resulting boronates were coupled via a microwave-mediated Suzuki-Miyaura reaction to afford a library of biarylethyl aryl and biarylethyl cycloalkyl derivatives. A complementary reaction sequence involved an initial Suzuki-Miyaura coupling. Crown Copyright (C) 2012 Published by Elsevier Ltd. All rights reserved.
• Jha, Rajeev Ranjan; Chaudhary, Ritu; Chandra, Ramesh, Journal of the Indian Chemical Society, 2011, vol. 88, # 8, p. 1187 - 1194
  作者：Jha, Rajeev Ranjan、Chaudhary, Ritu、Chandra, Ramesh、Verma, Akhilesh Kumar

  DOI：——

  日期：——
• Synthesis of Pharmaceutically Relevant Arylamines Enabled by a Nitroreductase from <i>Bacillus tequilensis</i>
  作者：Sara Russo、Alejandro Prats Luján、Marco W. Fraaije、Gerrit J. Poelarends

  DOI：10.1002/cbic.202300846

  日期：——

  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.