4'-methanesulfonyl-biphenyl-4-carbonitrile | 345222-97-1

• 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'-methanesulfonyl-biphenyl-4-carbonitrile
• 英文别名: 4'-(Methylsulfonyl)[1,1'-biphenyl]-4-carbonitrile；4-(4-methylsulfonylphenyl)benzonitrile
• CAS: 345222-97-1
• 化学式: C₁₄H₁₁NO₂S
• 分子量: 257.313
• InChiKey: ZBCFLHFZCDTCPV-UHFFFAOYSA-N

物化性质

• 沸点：
  481.8±45.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  66.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4'-methanesulfonyl-biphenyl-4-carbonitrile 、 二碳酸二叔丁酯 在 palladium 10% on activated carbon 、 氢气 作用下， 反应 18.0h， 以85%的产率得到(4'-methanesulfonyl-biphenyl-4-ylmethyl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Design and synthesis of substituted nicotinamides as inhibitors of soluble epoxide hydrolase

  摘要：

  A series of potent nicotinamide inhibitors of soluble epoxides hydrolase (sEH) is disclosed. This series was designed using structure-based deconstruction and a combination of two HTS hit series, resulting in hybrid analogs that retained the optimal potency from one series, and acceptable in vitro metabolic stability from the other. Structure-guided optimization of these analogs gave rise to nanomolar inhibitors of human sEH that had acceptable plasma exposure to qualify them as probes to determine the in vivo phenotypic consequences of sEH inhibition. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.08.074
• 作为产物：
  描述：

  4-溴苯腈 、 4-（甲磺酰基）苯硼酸 在 potassium fluoride 、 tris-(dibenzylideneacetone)dipalladium(0) 、 tri tert-butylphosphoniumtetrafluoroborate 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以44%的产率得到4'-methanesulfonyl-biphenyl-4-carbonitrile
  参考文献：
  名称：

  Design and synthesis of substituted nicotinamides as inhibitors of soluble epoxide hydrolase

  摘要：

  A series of potent nicotinamide inhibitors of soluble epoxides hydrolase (sEH) is disclosed. This series was designed using structure-based deconstruction and a combination of two HTS hit series, resulting in hybrid analogs that retained the optimal potency from one series, and acceptable in vitro metabolic stability from the other. Structure-guided optimization of these analogs gave rise to nanomolar inhibitors of human sEH that had acceptable plasma exposure to qualify them as probes to determine the in vivo phenotypic consequences of sEH inhibition. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.08.074

文献信息

• Substituted pyridineamide compounds useful as soluble epoxide hydrolase inhibitors
  申请人：Delombaert Stephane

  公开号：US20090099184A1

  公开（公告）日：2009-04-16

  Disclosed are compounds active against soluble epoxide hydrolase (sEH), compositions thereof and methods of using and making same.

  本发明涉及对可溶性环氧水解酶（sEH）活性的化合物，其组成物和使用和制造的方法。
• Palladium-Catalyzed Cyanation of Aryl Sulfonium Salts
  作者：Mengna Liu、Benqiang Cui、Chuntao Zhong、Yanhui Shi、Yanfeng Dang、Changsheng Cao

  DOI：10.1021/acs.orglett.3c00829

  日期：2023.6.9

  dimethylsulfonium salts using cheap, nontoxic, and bench-stable K4[Fe(CN)6]·3H2O as the cyanating reagent has been developed. The reactions proceeded well under base-free conditions with various sulfonium salts and provided aryl nitrile with yields of up to 92%. Aryl sulfides can be transformed to aryl nitriles directly via a one-pot process, and the protocol is scalable. Density functional theory calculations

  使用廉价、无毒且实验室稳定的 K 4 [Fe(CN) 6 ]·3H 2 O 作为氰化试剂，开发了钯催化的芳基二甲基锍盐氰化反应。该反应在无碱条件下使用各种硫鎓盐进行得很好，并以高达 92% 的产率提供芳基腈。芳基硫化物可以通过一锅法直接转化为芳基腈，并且该协议是可扩展的。进行密度泛函理论计算以研究涉及氧化加成、配体交换、还原消除和再生以产生产物的催化循环的反应机理。
• WO2007/98352
  申请人：——

  公开号：——

  公开（公告）日：——
• SUBSTITUTED PYRIDINEAMIDE COMPOUNDS USEFUL AS SOLUBLE EPOXIDE HYDROLASE INHIBITORS
  申请人：Boehringer Ingelheim International GmbH

  公开号：EP1987004A2

  公开（公告）日：2008-11-05
• [EN] SUBSTITUTED PYRIDINEAMIDE COMPOUNDS USEFUL AS SOLUBLE EPOXIDE HYDROLASE INHIBITORS<br/>[FR] PYRIDINEAMIDES SUBSTITUÉS POUVANT ÊTRE EMPLOYÉS EN TANT QU'INHIBITEURS D'ÉPOXYDE HYDROLASE SOLUBLE
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2007098352A2

  公开（公告）日：2007-08-30

  [EN] Disclosed are compounds active against soluble epoxide hydrolase (sEH), compositions thereof and methods of using and making same.
  [FR] La présente invention concerne des composés actifs contre l'époxyde hydrolase soluble (sEH), des compositions les contenant et leurs méthodes d'utilisation et de fabrication.