4-氯-3-(二甲基氨基羰基)苯硼酸 | 871332-76-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-氯-3-(二甲基氨基羰基)苯硼酸
• 中文别名: 4-氯-3-(二甲基甲酰氨)苯基硼酸
• 英文名称: 4-chloro-3-(dimethylcarbamoyl)phenylboronic acid
• 英文别名: (4-Chloro-3-(dimethylcarbamoyl)phenyl)boronic acid；[4-chloro-3-(dimethylcarbamoyl)phenyl]boronic acid
• CAS: 871332-76-2
• 化学式: C₉H₁₁BClNO₃
• mdl: MFCD07783868
• 分子量: 227.455
• InChiKey: ZTPXXLBYJKNIDH-UHFFFAOYSA-N

物化性质

• 熔点：
  164-166℃

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  60.8
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2931900090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

反应信息

• 作为反应物：
  描述：

  2-iodo-3-((2-((trimethylsilyl)ethynyl)-1,3-dioxolan-2-yl)methyl)-1H-indole 、 4-氯-3-(二甲基氨基羰基)苯硼酸 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 caesium carbonate 、 三(4-三氟甲苯基)膦 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 24.0h， 以36%的产率得到
  参考文献：
  名称：

  Exploring a cascade Heck–Suzuki reaction based route to kinase inhibitors using design of experiments

  摘要：

  通过钯催化串联反应组装了具有激酶抑制特性的融合三环系统。该反应使用统计实验设计进行了优化。

  DOI：

  10.1039/c4ob02694b

文献信息

• 1,2,4-Triazolsulfone: A novel isosteric replacement of acylsulfonamides in the context of Na V 1.7 inhibition
  作者：Alessandro A. Boezio、Kristin Andrews、Christiane Boezio、Margaret Chu-Moyer、Katrina W. Copeland、Erin F. DiMauro、Robert S. Foti、Robert T. Fremeau、Hua Gao、Stephanie Geuns-Meyer、Russell F. Graceffa、Hakan Gunaydin、Hongbing Huang、Daniel S. La、Joseph Ligutti、Bryan D. Moyer、Emily A. Peterson、Violeta Yu、Matthew M. Weiss

  DOI：10.1016/j.bmcl.2018.04.035

  日期：2018.6

  Recently, the identification of several classes of aryl sulfonamides and acyl sulfonamides that potently inhibit Na(v)1.7 and demonstrate high levels of selectivity over other Na-v isoforms have been reported. The fully ionizable nature of these inhibitors has been shown to be an important part of the pharmacophore for the observed potency and isoform selectivity. The requirement of this functionality, however, has presented challenges associated with optimization toward inhibitors with drug-like properties and minimal off-target activity. In an effort to obviate these challenges, we set out to develop an orally bioavailable, selective Na(v)1.7 inhibitor, lacking these acidic functional groups. Herein, we report the discovery of a novel series of inhibitors wherein a triazolesulfone has been designed to serve as a bioisostere for the acyl sulfonamide. This work culminated in the delivery of a potent series of inhibitors which demonstrated good levels of selectivity over Na v 1.5 and favorable pharmacokinetics in rodents. (C) 2018 Elsevier Ltd. All rights reserved.
• Exploring a cascade Heck–Suzuki reaction based route to kinase inhibitors using design of experiments
  作者：Andreas Ekebergh、Christine Lingblom、Peter Sandin、Christine Wennerås、Jerker Mårtensson

  DOI：10.1039/c4ob02694b

  日期：——

  A fused tricyclic system with kinase inhibiting properties was assembledviaa palladium catalyzed tandem reaction. The reaction was optimized using statistical experimental design.

  通过钯催化串联反应组装了具有激酶抑制特性的融合三环系统。该反应使用统计实验设计进行了优化。