N-isopropyl-2-nitrobenzamide | 947-79-5

• 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: N-isopropyl-2-nitrobenzamide
• 英文别名: N-Isopropyl-2-nitro-benzamid；2-nitro-N-propan-2-ylbenzamide
• CAS: 947-79-5
• 化学式: C₁₀H₁₂N₂O₃
• mdl: MFCD00830981
• 分子量: 208.217
• InChiKey: ZJMWYEHEWWSKQV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  74.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-isopropyl-2-nitrobenzamide 在 甲酸 、 palladium 10% on activated carbon 作用下， 生成 邻氨基苯甲酸异丙基胺
  参考文献：
  名称：

  Diversified facile synthesis of benzimidazoles, quinazolin-4(3H)-ones and 1,4-benzodiazepine-2,5-diones via palladium-catalyzed transfer hydrogenation/condensation cascade of nitro arenes under microwave irradiation

  摘要：

  一种高效的方法学已建立，用于在微波辐射下利用Pd-CTH/缩合级联反应在TEA-甲酸混合物中多样化制备苯并咪唑、喹唑啉-4(3H)-酮和1,4-苯二氮杂环己酮。

  DOI：

  10.1039/c4ra15765f
• 作为产物：
  描述：

  o-Nitroso-N-isopropylbenzamid 生成 N-isopropyl-2-nitrobenzamide
  参考文献：
  名称：

  BODIKOVA, ELENA, VOD. HOSP., 40,(1990) N, C. 216-220

  摘要：

  DOI：

文献信息

• 一种含氮杂环化合物的合成方法
  申请人：武汉理工大学

  公开号：CN105732519A

  公开（公告）日：2016-07-06

  本发明公开了一种含氮杂环化合物的合成方法。将邻硝基芳烃溶解于三乙胺?甲酸混合物，并加入Pd/C催化剂，130～180℃下微波照射反应5min～10min，反应后得到相应的含氮杂环化合物；所述邻硝基芳烃为邻硝基苯甲酰胺或邻硝基苯胺。本发明以邻硝基芳烃为起始原料，采用一种钯催化转移氢化还原?环缩合的方法在三乙胺?甲酸共沸混合物中及微波照射下将原料转化为产物，高效、环境友好且适用于多样化的底物，同时在生成产物的过程中无副反应发生。对反应产物用有机试剂萃取除去反应体系中的催化剂，旋蒸得到含氮杂环化合物纯品。无需柱层析色谱进行分离提纯。
• Metal and phosgene-free synthesis of 1H-quinazoline-2,4-diones by selenium-catalyzed carbonylation of o-nitrobenzamides
  作者：Xiaowei Wu、Zhengkun Yu

  DOI：10.1016/j.tetlet.2010.01.040

  日期：2010.3

  were efficiently synthesized by selenium-catalyzed carbonylation of o-nitrobenzamides under relatively mild conditions. In situ-generated carbonyl selenide (SeCO) is proposed to initiate the catalytic carbonylation. Thus, a concise transition metal and phosgene-free synthetic route to potentially bioactive-substituted 1H-quinazoline-2,4-dione derivatives has been developed.

  在相对温和的条件下，通过硒催化邻硝基苯甲酰胺的羰基化反应，可以有效地合成1 H-喹唑啉-2,4-二酮。建议原位产生的羰基硒化物（SeCO）引发催化羰基化反应。因此，已经开发出一种简明的过渡金属和无光气的合成路线，可以潜在地被生物活性取代的1 H-喹唑啉-2,4-二酮衍生物。
• Iron-Catalyzed One-Pot 2,3-Diarylquinazolinone Formation from 2-Nitrobenzamides and Alcohols
  作者：Huamin Wang、Xiangxiang Cao、Fuhong Xiao、Saiwen Liu、Guo-Jun Deng

  DOI：10.1021/ol402350x

  日期：2013.9.20

  A novel approach for the synthesis of 2,3-diarylquinazolinones using iron as catalyst is described. Various 2-nitro-N-arylbenzamides reacted with benzylic alcohols to selectively give the corresponding products in the absence of external oxidant or reductant.
• A B₂(OH)₄-Mediated Synthesis of 2-Substituted Indazolone and Its Application in a DNA-Encoded Library
  作者：Yapeng Bao、Zongfa Deng、Jing Feng、Weiwei Zhu、Jin Li、Jinqiao Wan、Guansai Liu

  DOI：10.1021/acs.orglett.0c02032

  日期：2020.8.21

  Indazolone cores are among the most common structural components in medicinal chemistry and can be found in many biologically active molecules. In this report, a mild and efficient approach to 2-substituted indazolones via B-2(OH)(4)-mediated reductive N-N bond formation is developed. This strategy features mild conditions, no request for a metal catalyst, and a wide scope for both aliphatic and aromatic amines. Meanwhile, this method was further successfully applied on DNA to construct indazolone cores for a DNA-encoded library. This will enable the production of a very attractive indazolone-cored library from simple amines and scaffolds, which will provide considerable diversity.
• Insecticidal anthranilic diamides: A new class of potent ryanodine receptor activators
  作者：George P. Lahm、Thomas P. Selby、John H. Freudenberger、Thomas M. Stevenson、Brian J. Myers、Gilles Seburyamo、Ben K. Smith、Lindsey Flexner、Christopher E. Clark、Daniel Cordova

  DOI：10.1016/j.bmcl.2005.08.034

  日期：2005.11

  A novel class of anthranilic diamides has been discovered with exceptional insecticidal activity on a range of Lepidoptera. These compounds have been found to exhibit their action by release of intracellular Ca2+ stores mediated by the ryanodine receptor. The discovery, synthesis, structure-activity, and biological results are presented. (c) 2005 Elsevier Ltd. All rights reserved.