(3-苄氧羰基-5-硝基苯)硼酸 | 380430-62-6

• 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: (3-苄氧羰基-5-硝基苯)硼酸
• 中文别名: 3-苄氧基羰基-5-硝基苯基硼酸
• 英文名称: 3-benzyloxycarbonyl-5-nitrophenylboronic acid
• 英文别名: (3-nitro-5-phenylmethoxycarbonylphenyl)boronic acid
• CAS: 380430-62-6
• 化学式: C₁₄H₁₂BNO₆
• mdl: MFCD03411934
• 分子量: 301.063
• InChiKey: YDPDKQXYZBUILB-UHFFFAOYSA-N

物化性质

• 熔点：
  140-148℃
• 沸点：
  537.1±60.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.52
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• 危险性防范说明：
  P261,P264,P271,P280,P302+P352,P304+P340+P312,P305+P351+P338,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H315,H319,H335

反应信息

• 作为反应物：
  描述：

  tert-butyl [6-bromo-3-(isopropylamino)-2-oxo-pyridin-1(2H)-yl]acetate 、 (3-苄氧羰基-5-硝基苯)硼酸 在 四(三苯基膦)钯 、 caesium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 16.0h， 以78%的产率得到benzyl 3-[1-(2-tert-butoxy-2-oxoethyl)-5-(isopropylamino)-6-oxo-1,6-dihydropyridin-2-yl]-5-nitrobenzoate
  参考文献：
  名称：

  Design, Synthesis, and Crystal Structure of Selective 2-Pyridone Tissue Factor VIIa Inhibitors

  摘要：

  Targeted 2-pyridones were selected as tissue Factor VIIa inhibitors and prepared from 2,6-dibromopyridine via a multistep synthesis. A variety of chemical transformations, including regioselective nucleophilic addition, selective nitrogen alkylation, and a Suzuki coupling, afforded the targeted tissue Factor VIIa inhibitors. The pyridone core was selected as a replacement for the pyrazinone core of noncovalent tissue Factor VIIa inhibitors and designed such that their substitution pattern would occupy and interact with the S-1, S-2, and S-3 pockets of the tissue Factor VIIa enzyme. These compounds were tested in several serine protease enzyme assays involved in the coagulation cascade exhibiting modest activity on tissue Factor VIIa with excellent selectivity over thrombin and Factor Xa. Finally, an X-ray crystal structure of inhibitor 14a bound to tissue Factor VIIa was obtained and will be described.

  DOI：

  10.1021/jm0301686

文献信息

• Synthesis of 2-pyridones as tissue factor VIIa inhibitors
  作者：John J Parlow、Michael S South

  DOI：10.1016/s0040-4020(03)01239-0

  日期：2003.9

  2-Pyridones were prepared from 2,6-dibromopyridine via a multi-step synthesis. A variety of chemical transformations, including regioselective nucleophilic addition and selective nitrogen alkylation, afforded the penultimate intermediate 9. A combination of two-dimensional NMR techniques to unequivocally assign the structure of 9 is described. Compound 9 was then used in a Suzuki coupling and further derivatized to afford the targeted tissue Factor VIIa inhibitors. These compounds were tested in several serine protease enzyme assays with biological activity reported. (C) 2003 Elsevier Ltd. All rights reserved.
• Design, Synthesis, and Crystal Structure of Selective 2-Pyridone Tissue Factor VIIa Inhibitors
  作者：John J. Parlow、Ravi G. Kurumbail、Roderick A. Stegeman、Anna M. Stevens、William C. Stallings、Michael S. South

  DOI：10.1021/jm0301686

  日期：2003.10.1

  Targeted 2-pyridones were selected as tissue Factor VIIa inhibitors and prepared from 2,6-dibromopyridine via a multistep synthesis. A variety of chemical transformations, including regioselective nucleophilic addition, selective nitrogen alkylation, and a Suzuki coupling, afforded the targeted tissue Factor VIIa inhibitors. The pyridone core was selected as a replacement for the pyrazinone core of noncovalent tissue Factor VIIa inhibitors and designed such that their substitution pattern would occupy and interact with the S-1, S-2, and S-3 pockets of the tissue Factor VIIa enzyme. These compounds were tested in several serine protease enzyme assays involved in the coagulation cascade exhibiting modest activity on tissue Factor VIIa with excellent selectivity over thrombin and Factor Xa. Finally, an X-ray crystal structure of inhibitor 14a bound to tissue Factor VIIa was obtained and will be described.