[(2-甲基苯基)氨基](氧代)乙酸 | 406190-09-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: [(2-甲基苯基)氨基](氧代)乙酸
• 中文别名: 2-[(2-甲基苯基)氨基]-2-氧代-乙酸；邻-甲基2-氧代-2-苯胺基乙酸；2-[(2-甲基苯基)氨基]-2-乙醛酸；2-氧代-2-[(2-甲基苯基)氨基]乙酸；N-邻甲苯基-氨基草酸
• 英文名称: 2-oxo-2-(o-tolylamino)acetic acid
• 英文别名: [(2-Methylphenyl)amino](oxo)acetic acid；2-(2-methylanilino)-2-oxoacetic acid
• CAS: 406190-09-8
• 化学式: C₉H₉NO₃
• mdl: MFCD01001244
• 分子量: 179.175
• InChiKey: PORKFZUSLXVORE-UHFFFAOYSA-N

物化性质

• 密度：
  1.342±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  [(2-甲基苯基)氨基](氧代)乙酸 在 草酰氯 作用下， 以 二氯甲烷 为溶剂， 生成 o-tolyl-aminooxalyl chloride
  参考文献：
  名称：

  The design, synthesis and in vitro immunosuppressive evaluation of novel isobenzofuran derivatives

  摘要：

  The synthesis and biological evaluation of a series of novel isobenzofuran-based compounds are described. The compounds were evaluated for their immunosuppressive effects of T-cell proliferation and IMPDH type II inhibitor activity in vitro, as well as their structure-activity relationships were assessed. Several compounds demonstrated highly efficacious immunosuppressive properties, especially compounds 2d, 2e, 2h and 2j, which were superior to MPA, while compounds 2k, 2m, 2n, 4c and 5d exhibited an equipotent inhibitory activity compared to MPA. Generally, it was obviously demonstrated that alpha,beta-unsaturated amides proved more potent than the diamide and urea series. The present study provides a guide for further research on development of safe and effective immunosuppressive agents. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.11.078
• 作为产物：
  描述：

  邻甲苯胺 在 三乙胺 、 lithium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 [(2-甲基苯基)氨基](氧代)乙酸
  参考文献：
  名称：

  Sengupta, Saumitra; Rao, G. Venkateshwar; Dubey, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2011, vol. 50, # 7, p. 901 - 905

  摘要：

  DOI：

文献信息

• [EN] DIKETOPIPERAZINE DERIVATIVES AS P2X7 MODULATORS<br/>[FR] DÉRIVÉS DE DICÉTOPIPÉRAZINE COMME MODULATEURS DE P2X7
  申请人：GLAXO GROUP LTD

  公开号：WO2010125103A1

  公开（公告）日：2010-11-04

  The invention provides a compound of formula (I) or a pharmaceutically acceptable salt thereof: (I) wherein: A represents an aryl, heteroaryl or heterocyclyl group; and any ring or ring system of said aryl or heteroaryl is optionally substituted with 1 to 3 substituents, which may be the same or different, selected from the group consisting of halogen, C1-6 alkyl, -CF3, - OCF3, cyano, C1-6 alkoxy, -NR10R11, -X-aryl, -X-heteroaryl and -X-heterocyclyl; R1, R2, R3, R4 and R5 independently represent hydrogen, fluorine, chlorine, -CF3, cyano or C1-6 alkyl, such that at least one of R1, R2, R3, R4 and R5 is other than hydrogen; R6, R7, R8, R9, R10 and R11 independently represent hydrogen or C1-6 alkyl; X represents a linker selected from a bond, -(CH2)n- and -O-(CH2)n-; and n represents an integer from 1 to 3. The compounds or salts modulate P2X7 receptor function and are capable of antagonizing the effects of ATP at the P2X7 receptor ("P2X7 receptor antagonists").

  本发明提供了一种式(I)化合物或其药学上可接受的盐：(I)其中：A代表芳基、杂芳基或杂环基团；上述芳基或杂芳基的任何环或环系可选地被1至3个取代基取代，这些取代基可以相同或不同，选自卤素、C1-6烷基、-CF3、-OCF3、氰基、C1-6烷氧基、-NR10R11、-X-芳基、-X-杂芳基和-X-杂环基；R1、R2、R3、R4和R5各自独立地代表氢、氟、氯、-CF3、氰基或C1-6烷基，使得R1、R2、R3、R4和R5中至少有一个不是氢；R6、R7、R8、R9、R10和R11各自独立地代表氢或C1-6烷基；X代表连接子，选自键、-(CH2)n-和-O-(CH2)n-；n代表1至3的整数。这些化合物或盐能够调节P2X7受体功能，并能拮抗ATP在P2X7受体上的效应（“P2X7受体拮抗剂”）。
• Silver-catalyzed direct C–H oxidative carbamoylation of quinolines with oxamic acids
  作者：Jin-Wei Yuan、Qian Chen、Chuang Li、Jun-Liang Zhu、Liang-Ru Yang、Shou-Ren Zhang、Pu Mao、Yong-Mei Xiao、Ling-Bo Qu

  DOI：10.1039/d0ob00358a

  日期：——

  A silver-catalyzed efficient and direct C-H carbamoylation of quinolines with oxamic acids to access carbamoylated quinolines has been developed through oxidative decarboxylation reaction. The reaction proceeds smoothly over a broad range of substrates with excellent functional group tolerance and excellent yields under mild conditions.

  通过氧化脱羧反应，已开发出一种银催化的喹啉与草酰胺酸的直接催化高效氨基甲酸酯化反应，以得到氨基甲酰化的喹啉。该反应在温和的条件下，可在各种底物上顺利进行，具有出色的官能团耐受性和出色的收率。
• Photocatalyzed synthesis of unsymmetrical ureas via the oxidative decarboxylation of oxamic acids with PANI-g-C3N4-TiO2 composite under visible light
  作者：Liang Wang、Hao Wang、Yaoyao Wang、Minggui Shen、Shubai Li

  DOI：10.1016/j.tetlet.2020.151962

  日期：2020.6

  The synthesis of unsymmetrical ureas via the photocatalyzed oxidative decarboxylation of oxamic acids has been developed. The carbamoyl radicals were generated from oxamic acids in the presence of a hypervalent iodine reagent and the PANI(Polyaniline)-g-C3N4-TiO2 composite under visible light irradiation. The radicals were converted in situ into the corresponding isocyanates, which were then trapped

  已经开发了通过光催化的草酰胺酸氧化脱羧合成不对称脲的方法。在高价碘试剂和PANI（聚苯胺）-gC 3 N 4 -TiO 2复合材料的存在下，由草酰胺酸在可见光照射下生成氨基甲酰基自由基。自由基被原位转化进入相应的异氰酸酯，然后被胺捕获，以中等至良好的产率得到相应的产物。该方案避免了直接使用对环境不利的异氰酸酯，并且可以耐受一系列底物。而且，光催化剂可以通过简单的过滤而容易地回收，并且可以在仅轻微降低催化活性的情况下重复使用几次。
• Persulfate promoted tandem radical cyclization of ortho-cyanoarylacrylamides with oxamic acids for construction of carbamoyl quinoline-2,4-diones under metal-free conditions
  作者：Qing-Qing Han、Yuan-Yuan Sun、Shao-Hui Yang、Jing-Cheng Song、Zu-Li Wang

  DOI：10.1016/j.cclet.2021.04.019

  日期：2021.11

  An efficient and practical methods for the synthesis of carbamoyl quinoline-2,4-diones via the reaction of ortho-cyanoarylacrylamides with oxamic acids was described. This cyclic reaction could be performed efficiently under metal free conditions. Various products with functional groups could be obtained with moderate to high yields via radical mechanism.

  描述了一种通过邻-氰基芳基丙烯酰胺与草酸反应合成氨基甲酰基喹啉-2,4-二酮的有效且实用的方法。这种循环反应可以在无金属条件下有效地进行。通过自由基机理，可以以中高产率获得各种带有官能团的产物。
• From isocyanides to trichloropyruvamides: application to a new preparation of oxamide derivatives
  作者：Laurent El Kaim、Laetitia Gaultier、Laurence Grimaud、Emilie Vieu

  DOI：10.1016/j.tetlet.2004.08.169

  日期：2004.10

  Isocyanides react readily with trichloroacetic acid anhydride forming stable hydrates of trichloropyruvamides. These compounds are valuable intermediates for obtaining oxamides by reaction with TMSCl/NEt3 followed by addition of an amine.

  异氰化物易于与三氯乙酸酐反应，形成稳定的三氯丙酮酰胺水合物。这些化合物是有价值的中间体，可通过与TMSC1 / NEt 3反应，然后添加胺来获得草酰胺。