tert-butyl 4-formyl-3-nitrobenzoate | 321886-31-1

• 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: tert-butyl 4-formyl-3-nitrobenzoate
• 英文别名: 4-formyl-3-nitro-benzoic acid tert-butyl ester；4-Formyl-3-nitro-benzoic acid tert-butyl ester
• CAS: 321886-31-1
• 化学式: C₁₂H₁₃NO₅
• 分子量: 251.239
• InChiKey: XUVIIKSNXAUPCY-UHFFFAOYSA-N

物化性质

• 沸点：
  393.5±32.0 °C(Predicted)
• 密度：
  1.253±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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-formyl-3-nitrobenzoate 在 N-甲基吗啉 、 Jones reagent 、 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 、 二乙胺 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 、 丙酮 、 乙腈 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 32.5h， 生成 (R)-tert-butyl 1-(4-cyclohexylbenzyl)-3-isobutyl-2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepine-8-carboxylate
  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
• 作为产物：
  描述：

  4-甲基-3-硝基苯甲酸 在 4-二甲氨基吡啶 、 N,N-二甲基甲酰胺二甲基缩醛 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 tert-butyl 4-formyl-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

• Bicyclic antagonists selective for the &agr;v&bgr;3 integrin
  申请人：Wyeth

  公开号：US06429214B1

  公开（公告）日：2002-08-06

  This invention provides novel bicyclic compounds of Formula (I): wherein u, v, m, Y, G, A—B, R1, R1a, R2, R4, R5, R5a, and R5b are defined in the specification which compounds exhibit activity as inhibitors of bone resorption and compounds of Formula (II) wherein u, v, m, Y, G, D, A—B, R1, R1a, R2, R3, R4, R5, R5a, and R5b are defined in the specification which compounds exhibit activity as inhibitors of bone resorption.

  这项发明提供了式（I）的新颖双环化合物：其中u、v、m、Y、G、A—B、R1、R1a、R2、R4、R5、R5a和R5b在规范中定义，这些化合物表现出作为骨吸收抑制剂的活性；以及式（II）的化合物：其中u、v、m、Y、G、D、A—B、R1、R1a、R2、R3、R4、R5、R5a和R5b在规范中定义，这些化合物表现出作为骨吸收抑制剂的活性。
• Bicyclic antagonists selective for the alphavbeta3 integrin
  申请人：Wyeth

  公开号：US20030109523A1

  公开（公告）日：2003-06-12

  This invention provides novel bicyclic compounds of Formula (I): 1 wherein u, v, m, Y, G, A-B, R 1 , R 1a , R 2 , R 4 , R 5 , R 5a , and R 5b are defined in the specification which compounds exhibit activity as inhibitors of bone resorption and compounds of Formula (II) 2 wherein u, v, m, Y, G, D, A-B, R 1 , R 1a , R 2 , R 3 R 4 , R 5 , R 5a , and R 5b are defined in the specification which compounds exhibit activity as inhibitors of bone resorption.

  这项发明提供了公式（I）的新型双环化合物：其中u、v、m、Y、G、A-B、R1、R1a、R2、R4、R5、R5a和R5b在规范中有定义，这些化合物表现出抑制骨吸收的活性，以及公式（II）的化合物：其中u、v、m、Y、G、D、A-B、R1、R1a、R2、R3、R4、R5、R5a和R5b在规范中有定义，这些化合物也表现出抑制骨吸收的活性。
• 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.
• Orally active zwitterionic factor Xa inhibitors with long duration of action
  作者：Akiyoshi Mochizuki、Tsutomu Nagata、Hideyuki Kanno、Daisuke Takano、Masamichi Kishida、Makoto Suzuki、Toshiharu Ohta

  DOI：10.1016/j.bmcl.2011.10.021

  日期：2011.12

  We have optimized 2-aminomethylphenylamine derivative as a factor Xa inhibitor. Several polar functional groups were introduced in the central phenyl ring, and we focused on zwitter ionic compound showing continuous inhibitory activity in oral administration test. In vitro and oral activities were improved by optimization of S1 and S4 ligands. Incorporating the interaction with S1-beta pocket enhanced in vitro factor Xa inhibitory activity to less than 1 nM. Many zwitter ionic compounds showed long duration of action and potent inhibitory activity and high AUC values in oral administration tests to monkeys. (C) 2011 Elsevier Ltd. All rights reserved.
• Selective Colorimetric Sensing of Anions in Aqueous Media through Reversible Covalent Bonding
  作者：Dae-Sik Kim、Yun-Mi Chung、Mieun Jun、Kyo Han Ahn

  DOI：10.1021/jo900573v

  日期：2009.7.3

  Selective colorimetric sensing of anions in aqueous media has been studied, which involves reversible covalent bonding as key binding interactions. By introducing a simple nitro chromophore into an o-(carboxamido)trifluoroacetophenone ionophore that recognizes anions through reversible covalent bonding, we have realized a complete selectivity in colorimetric sensing of cyanide among competing anions such as fluoride. acetate, and dihydrogen phosphate in aqueous media. Such selectivity is explained by dominant reversible covalent bonding over hydrogen bonding, which leads to indirect internal charge transfer. The sensing system is readily converted into a polymeric analogue, demonstrating its potential applicability to develop a naked eye detection material for highly toxic cyanide ions.