4-(1-硝基乙基)苯甲酸甲酯 | 121408-12-6

• 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: 4-(1-硝基乙基)苯甲酸甲酯
• 英文名称: 4-(1-nitroethyl)benzoic acid methyl ester
• 英文别名: methyl 4-(1-nitroethyl)benzoate；Benzoic acid, 4-(1-nitroethyl)-, methyl ester
• CAS: 121408-12-6
• 化学式: C₁₀H₁₁NO₄
• 分子量: 209.202
• InChiKey: AUZRQFIWDBZKMI-UHFFFAOYSA-N

物化性质

• 熔点：
  49 °C
• 沸点：
  321.5±17.0 °C(Predicted)
• 密度：
  1.204±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(1-硝基乙基)苯甲酸甲酯 在 sodium tetrahydroborate 、 nickel chloride hexahydrate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 5.5h， 生成 methyl 4-(2-methyl-5-oxo-pyrrolidin-2-yl)benzoate
  参考文献：
  名称：

  Synthesis of 5-alkyl-5-aryl-γ-lactams from 1-aryl-substituted nitroalkanes and methyl acrylate via Michael addition and reductive lactamization

  摘要：

  A general method for accessing 5-alkyl-5-aryl-gamma-lactams has been developed using readily available aryl bromides, nitroalkanes, and methyl acrylate as the starting materials. The palladium-catalyzed arylation of nitroalkanes gave the 1-aryl-substituted nitroalkanes, which underwent the DBU-mediated Michael addition with methyl acrylate at room temperature to afford the methyl 4-aryl-4-nitroalkanoates. The latter were then subjected to the nitro reduction using NaBH4-NiCl2 center dot 6H(2)O in MeOH at 0 degrees C to furnish, after treatment with aqueous K2CO3 at room temperature, the 5-alkyl-5-aryl-gamma-lactams in good to excellent overall yields. Selected examples of N-alkylation of the gamma-lactams were also illustrated. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.04.074
• 作为产物：
  描述：

  4-(1-羟基乙基)苯甲酸甲酯 在 盐酸 、 溶剂黄146 、 sodium nitrite 作用下， 以 二氯甲烷 为溶剂， 反应 5.5h， 以92%的产率得到4-(1-硝基乙基)苯甲酸甲酯
  参考文献：
  名称：

  Baruah, Apurba; Kalita, Biswajit; Barua, Nabin C., Synlett, 2000, # 7, p. 1064 - 1066

  摘要：

  DOI：

文献信息

• Synthesis of 5-alkyl-5-aryl-1-pyrroline N-oxides from 1-aryl-substituted nitroalkanes and acrolein via Michael addition and nitro reductive cyclization
  作者：Jingjing Xu、Xingyao Li、Jinlong Wu、Wei-Min Dai

  DOI：10.1016/j.tet.2014.07.046

  日期：2014.9

  A general method for accessing 5-alkyl-5-aryl-1-pyrroline N-oxides (AAPOs) has been established using readily available aryl bromides, nitroalkanes, and acrolein as the starting materials. The palladium-catalyzed arylation of nitroalkanes gave the 1-aryl-substituted nitroalkanes, which underwent the Et3N-catalyzed Michael addition with acrolein at room temperature to afford the 4-aryl-4-nitroaldehydes

  已经建立了使用5-芳基-5-芳基-1-吡咯啉N-氧化物（AAPO）的通用方法，该方法使用易得的芳基溴化物，硝基烷烃和丙烯醛作为起始原料。钯催化的硝基烷的芳基化反应生成了1-芳基取代的硝基烷，在室温下将其与丙烯醛一起进行了Et 3 N催化的迈克尔加成反应，得到了4-芳基-4-硝基醛。然后将其在0°C下使用Zn-HOAc在EtOH中的溶液进行硝基还原环化，然后将反应混合物加热至室温24小时，从而提供5-烷基-5-芳基-1-吡咯啉N-氧化物总体产量高。还描述了环硝酮与甲基丙烯酸甲酯的1，3-偶极环加成的选定实例。
• IMIDAZOPYRIDINE COMPOUNDS
  申请人：Astellas Pharma Inc.

  公开号：US20150232464A1

  公开（公告）日：2015-08-20

  [Problem] A pharmaceutical composition for treating or preventing various cardiovascular diseases, which have sGC activities based on improvement of cGMP signals, is provided. [Means for Solution] It was found that imidazo[1,2-a]pyridine compounds having a carbamoyl group at the 3-position and a particular cyclic group at the 8-position via a methyleneoxy group, or a salt thereof have sGC activation, and are useful as active ingredients of pharmaceutical compositions for treating or preventing various sGC-related cardiovascular diseases, in particular, peripheral arterial diseases, intermittent claudication, critical limb ischemia, hypertension, and pulmonary hypertension, thereby completing the present invention.

  提供一种用于治疗或预防各种心血管疾病的药物组合物，该组合物基于改善cGMP信号的sGC活性。发现在3-位置具有羰胺基团和通过亚甲氧基团在8-位置具有特定环状基团的咪唑并[1,2-a]吡啶化合物或其盐具有sGC激活作用，并且可用作治疗或预防各种sGC相关心血管疾病的药物组合物的活性成分，特别是外周动脉疾病、间歇性跛行、危重肢体缺血、高血压和肺动脉高压，从而完成了本发明。
• Imidazopyridine compounds
  申请人：ASTELLAS PHARMA INC.

  公开号：US09278968B2

  公开（公告）日：2016-03-08

  [Problem] A pharmaceutical composition for treating or preventing various cardiovascular diseases, which have sGC activities based on improvement of cGMP signals, is provided. [Means for Solution] It was found that imidazo[1,2-a]pyridine compounds having a carbamoyl group at the 3-position and a particular cyclic group at the 8-position via a methyleneoxy group, or a salt thereof have sGC activation, and are useful as active ingredients of pharmaceutical compositions for treating or preventing various sGC-related cardiovascular diseases, in particular, peripheral arterial diseases, intermittent claudication, critical limb ischemia, hypertension, and pulmonary hypertension, thereby completing the present invention.

  [问题]提供了一种用于治疗或预防基于cGMP信号改善的sGC活性的各种心血管疾病的药物组合物。 [解决方案的手段]发现在3位具有氨基甲酰基和通过亚甲氧基固定的特定环状基团在8位的咪唑并[1,2-a]吡啶化合物或其盐具有sGC激活作用，并且作为药物组合物的活性成分，用于治疗或预防各种sGC相关心血管疾病，特别是外周动脉疾病，间歇性跛行，危重肢体缺血，高血压和肺动脉高压，从而完成了本发明。
• Palladium-Catalyzed Monoarylation of Nitroalkanes
  作者：Erasmus M. Vogl、Stephen L. Buchwald

  DOI：10.1021/jo010953v

  日期：2002.1.1

  A general protocol for the Pd-catalyzed-arylation of nitroalkanes is described. Substituted aryl bromides as well as aryl chlorides can be coupled efficiently with a variety of nitroalkanes under mild conditions to selectively yield the monoarylated products. This method tolerates a number of functional groups including ketones, esters, and olefins. Notably, the arylation of nitroalkanes can be effected chemoselectively over ketone and ester arylation.
• US9278968B2
  申请人：——

  公开号：US9278968B2

  公开（公告）日：2016-03-08