2-chloro-N-methyl-4-nitro-N-phenylbenzamide | 183495-93-4

• 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: 2-chloro-N-methyl-4-nitro-N-phenylbenzamide
• CAS: 183495-93-4
• 化学式: C₁₄H₁₁ClN₂O₃
• mdl: MFCD01188679
• 分子量: 290.706
• InChiKey: AFTORZVTKYKHCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  66.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-chloro-N-methyl-4-nitro-N-phenylbenzamide 在 ferrous(II) sulfate heptahydrate 、 水 作用下， 以 甲醇 、 硝基甲烷 为溶剂， 反应 0.69h， 生成
  参考文献：
  名称：

  高价碘（III）介导的芳胺氧化脱芳香化环化

  摘要：

  AbstractAn oxidative dearomatizing cyclization of arylamines promoted by iodobenzene bis(trifluoroacetate) [PhI(CF3CO2)2] has been explored, leading to a novel synthetic approach to functionalized spirocyclic building blocks containing the structurally unique dieniminium moiety. This unprecedented methodology, featuring oxidative dearomatization and carbon‐carbon bond‐forming cyclization, to some extent, not only expands the synthetic potential of hypervalent iodine chemistry, but also enriches the oxidation chemistry of arylamines.magnified image

  DOI：

  10.1002/adsc.201400191
• 作为产物：
  描述：

  2-氯-4-硝基苯甲酸 在 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 生成 2-chloro-N-methyl-4-nitro-N-phenylbenzamide
  参考文献：
  名称：

  高价碘（III）介导的芳胺氧化脱芳香化环化

  摘要：

  AbstractAn oxidative dearomatizing cyclization of arylamines promoted by iodobenzene bis(trifluoroacetate) [PhI(CF3CO2)2] has been explored, leading to a novel synthetic approach to functionalized spirocyclic building blocks containing the structurally unique dieniminium moiety. This unprecedented methodology, featuring oxidative dearomatization and carbon‐carbon bond‐forming cyclization, to some extent, not only expands the synthetic potential of hypervalent iodine chemistry, but also enriches the oxidation chemistry of arylamines.magnified image

  DOI：

  10.1002/adsc.201400191

文献信息

• Microwave assisted synthesis of phenanthridinones and dihydrophenanthridines by vasicine/KOtBu promoted intramolecular C–H arylation
  作者：Sushila Sharma、Manoranjan Kumar、Shruti Sharma、Onkar S. Nayal、Neeraj Kumar、Bikram Singh、Upendra Sharma

  DOI：10.1039/c6ob01362g

  日期：——

  simple, efficient, rapid and transition metal-free methodology has been developed by utilizing vasicine (a natural product), as a catalyst for the synthesis of phenanthridinones and dihydrophenanthridines. The reaction proceeds through intramolecular C–H arylation with aryl halides in the presence of KOtBu as a base under microwave irradiation in sulfolane as a solvent. The reaction proceeds well with various

  已经开发了一种简单，有效，快速且无过渡金属的方法，该方法通过利用vasicine（天然产物）作为合成菲啶酮和二氢菲啶的催化剂。通过分子内C-H芳基化反应的进行，在KO的存在下芳基卤化物吨卜如在环丁砜微波辐射下碱作为溶剂。该反应在使用各种芳基碘，溴化物的情况下进行得很好，而在反应性较低的芳基氯化物下反应则更为显着，持续15分钟，从而以45-90％的收率提供了相应的产物。
• BENZAMIDE DERIVATIVES AS VASOPRESSIN ANTAGONISTS
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：EP0757670B1

  公开（公告）日：1999-01-13
• US6211242B1
  申请人：——

  公开号：US6211242B1

  公开（公告）日：2001-04-03
• [EN] BENZAMIDE DERIVATIVES AS VASOPRESSIN ANTAGONISTS<br/>[FR] DERIVES DE BENZAMIDE UTILISES COMME ANTAGONISTES DE LA VASOPRESSINE
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：WO1995029152A1

  公开（公告）日：1995-11-02

  (EN) This invention relates to new benzamide derivatives having a vasopressin antagonistic activity, etc. and represented by general formula (I), wherein R1 is aryl optionally substituted with lower alkyl, etc., R2 is lower alkyl, etc., R3 is hydrogen, etc., R4 is aryl, etc., X is CH or N, and Y is CH or N, and pharmaceutically acceptable salts thereof, to processes for the preparation thereof and to a pharmaceutical composition comprising the same.(FR) L'invention porte sur de nouveaux dérivés de benzamide, agissant comme antagonistes de la vasopressine et présentant la formule générale (I) où R1 représente un aryle éventuellement substitué par un alkyle inférieur, etc., R2 représente un alkyle inférieur, etc., R3 représente un hydrogène, etc., R4 représente un aryle, etc., X représente CH ou N, et Y représente CH ou N, ainsi que sur leurs sels pharmacocompatibles, sur leur méthode de préparation, et sur une composition pharmaceutique les contenant.
• Hypervalent Iodine(III)-Mediated Oxidative Dearomatizing Cyclization of Arylamines
  作者：Cong-Yang Jin、Ji-Yuan Du、Chao Zeng、Xian-He Zhao、Ye-Xing Cao、Xiang-Zhi Zhang、Xin-Yun Lu、Chun-An Fan

  DOI：10.1002/adsc.201400191

  日期：2014.8.11

  AbstractAn oxidative dearomatizing cyclization of arylamines promoted by iodobenzene bis(trifluoroacetate) [PhI(CF3CO2)2] has been explored, leading to a novel synthetic approach to functionalized spirocyclic building blocks containing the structurally unique dieniminium moiety. This unprecedented methodology, featuring oxidative dearomatization and carbon‐carbon bond‐forming cyclization, to some extent, not only expands the synthetic potential of hypervalent iodine chemistry, but also enriches the oxidation chemistry of arylamines.magnified image