tert-butyl 4-acetyl-3-nitrobenzoate | 1395101-70-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyl 4-acetyl-3-nitrobenzoate
• 英文别名: Tert-butyl 4-acetyl-3-nitrobenzoate
• CAS: 1395101-70-8
• 化学式: C₁₃H₁₅NO₅
• 分子量: 265.266
• InChiKey: DYAUKUYJOIKVJV-UHFFFAOYSA-N

物化性质

• 沸点：
  404.9±30.0 °C(Predicted)
• 密度：
  1.204±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  89.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl 4-acetyl-3-nitrobenzoate 在 tin(II) chloride dihdyrate 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 20.0h， 以94%的产率得到tert-butyl 3-methylbenzo[c]isoxazole-6-carboxylate
  参考文献：
  名称：

  One-pot synthesis of 2,1-benzisoxazoles (anthranils) by a stannous chloride-mediated tandem reduction–heterocyclization of 2-nitroacylbenzenes under neutral conditions

  摘要：

  Classically, 2,1-benzisoxazoles (anthranils) are prepared from 2-nitroacylbenzenes by a reductive heterocyclization reaction with Sn or SnCl2 concentrated HCl. Acid sensitive functionalities are expected to be incompatible with these conditions; milder approaches to the synthesis of 2,1-benzisoxazoles would be welcomed. We demonstrate that SnCl2 center dot 2H(2)O in a 1:1 mixture of EtOAc/MeOH is capable of mediating the tandem reduction-heterocyclization of a variety of 2-nitroacylbenzenes to their corresponding 2,1-benzisoxazoles in good to excellent yields under essentially neutral conditions. Importantly, several commonly used acid-labile protecting groups, including Boc carbamate, tert-butyl ether, and tert-butyl ester, proved orthogonal to these reaction conditions. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.07.006
• 作为产物：
  描述：

  对乙基苯甲酸 在 chromium(VI) oxide 、 4-二甲氨基吡啶 、 硫酸 、 硝酸 、 高碘酸 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 20.0h， 生成 tert-butyl 4-acetyl-3-nitrobenzoate
  参考文献：
  名称：

  Synthetic, structural mimetics of the β-hairpin flap of HIV-1 protease inhibit enzyme function

  摘要：

  Small-molecule mimetics of the beta-hairpin flap of HIV-1 protease (HIV-1 PR) were designed based on a 1,4-benzodiazepine scaffold as a strategy to interfere with the flap-flap protein-protein interaction, which functions as a gated mechanism to control access to the active site. Michaelis-Menten kinetics suggested our small-molecules are competitive inhibitors, which indicates the mode of inhibition is through binding the active site or sterically blocking access to the active site and preventing flap closure, as designed. More generally, a new bioactive scaffold for HIV-1PR inhibition has been discovered, with the most potent compound inhibiting the protease with a modest K-i of 11 mu M. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.09.002

文献信息

• Synthetic, structural mimetics of the β-hairpin flap of HIV-1 protease inhibit enzyme function
  作者：Jay Chauhan、Shen-En Chen、Katherine J. Fenstermacher、Aurash Naser-Tavakolian、Tali Reingewertz、Rosene Salmo、Christian Lee、Emori Williams、Mithun Raje、Eric Sundberg、Jeffrey J. DeStefano、Ernesto Freire、Steven Fletcher

  DOI：10.1016/j.bmc.2015.09.002

  日期：2015.11

  Small-molecule mimetics of the beta-hairpin flap of HIV-1 protease (HIV-1 PR) were designed based on a 1,4-benzodiazepine scaffold as a strategy to interfere with the flap-flap protein-protein interaction, which functions as a gated mechanism to control access to the active site. Michaelis-Menten kinetics suggested our small-molecules are competitive inhibitors, which indicates the mode of inhibition is through binding the active site or sterically blocking access to the active site and preventing flap closure, as designed. More generally, a new bioactive scaffold for HIV-1PR inhibition has been discovered, with the most potent compound inhibiting the protease with a modest K-i of 11 mu M. (C) 2015 Elsevier Ltd. All rights reserved.
• One-pot synthesis of 2,1-benzisoxazoles (anthranils) by a stannous chloride-mediated tandem reduction–heterocyclization of 2-nitroacylbenzenes under neutral conditions
  作者：Jay Chauhan、Steven Fletcher

  DOI：10.1016/j.tetlet.2012.07.006

  日期：2012.9

  Classically, 2,1-benzisoxazoles (anthranils) are prepared from 2-nitroacylbenzenes by a reductive heterocyclization reaction with Sn or SnCl2 concentrated HCl. Acid sensitive functionalities are expected to be incompatible with these conditions; milder approaches to the synthesis of 2,1-benzisoxazoles would be welcomed. We demonstrate that SnCl2 center dot 2H(2)O in a 1:1 mixture of EtOAc/MeOH is capable of mediating the tandem reduction-heterocyclization of a variety of 2-nitroacylbenzenes to their corresponding 2,1-benzisoxazoles in good to excellent yields under essentially neutral conditions. Importantly, several commonly used acid-labile protecting groups, including Boc carbamate, tert-butyl ether, and tert-butyl ester, proved orthogonal to these reaction conditions. (C) 2012 Elsevier Ltd. All rights reserved.