2-oxo-2-(m-tolylamino)acetic acid | 17738-78-2

• 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
• 英文名称: 2-oxo-2-(m-tolylamino)acetic acid
• 英文别名: 3-Methyl-oxanilsaeure；N-(m-tolyl)-oxamic acid；m-tolyl-oxalamic acid；m-Tolyl-oxalamidsaeure；Oxalsaeure-mono-m-toluidid；m-Tolyloxamidsaeure；[(3-Methylphenyl)carbamoyl]formic acid；2-(3-methylanilino)-2-oxoacetic acid
• CAS: 17738-78-2
• 化学式: C₉H₉NO₃
• mdl: MFCD04366607
• 分子量: 179.175
• InChiKey: HYFAJKPUCQPCAZ-UHFFFAOYSA-N

物化性质

• 熔点：
  123 °C(Solv: water (7732-18-5))
• 密度：
  1.342±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-oxo-2-(m-tolylamino)acetic acid 在 1-羟基苯并三唑 、 戴斯-马丁氧化剂 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 苯甲醚 、 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-5-(2,6-difluorophenoxy)-3-[(3-methyl-phenylaminooxalyl)-amino]-4-oxo-pentanoic acid
  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：
• 作为产物：
  描述：

  3-甲基苯胺 在 三乙胺 、 lithium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 2-oxo-2-(m-tolylamino)acetic acid
  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

• 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。
• Radical Arylaminoformylation of Activated Alkenes to Amides Containing All‐Carbon Quaternary Stereocenters
  作者：Jing Liu、Baohui Zhang、Junjie Hu、Zhenpeng Qiu、Xinyan Chen、Xianxiang Tian、Qi Wang、Guohua Zheng、Ming Yuan

  DOI：10.1002/ejoc.202201378

  日期：2023.2.6

  The Ag+/S2O82−-inducted radical process for functionalized succinyl diamides bearing a α-quaternary carbon center through one-pot aminoformylation/aryl-migration/desulfonylation cascade has been proposed. This protocol with good tolerance to oxygen and water provides a complementary way for the aminoformylation/aromatization of alkenes as well.

  已经提出了通过一锅法氨甲酰化/芳基迁移/脱磺酰化级联的 Ag + /S 2 O 8 2−诱导自由基过程用于带有 α-季碳中心的功能化琥珀酰二胺。该方案对氧气和水具有良好的耐受性，也为烯烃的氨基甲酰化/芳构化提供了一种补充方式。
• (NH₄)₂S₂O₈ promoted tandem radical cyclization of quinazolin-4(3<i>H</i>)-ones with oxamic acids for the construction of fused quinazolinones under metal-free conditions
  作者：Shenyuan Gao、Menglu Cai、Gang Xu、Qiaolin Jin、Xiaozhong Wang、Linze Xu、Lixiang Wang、Liyan Dai

  DOI：10.1039/d3ob02081a

  日期：——

  A novel cascade radical addition/cyclization reaction of non-activated olefins and oxamic acids has been proposed. Under transition metal-free conditions, 36 quinazolinone derivatives containing an amide moiety were successfully synthesized, with the highest yield being 81%. This method involves the preparation of aminoacyl fused quinazolinone derivatives under mild conditions, offering advantages

  提出了一种非活化烯烃和草酸的新型级联自由基加成/环化反应。在无过渡金属条件下，成功合成了36种含有酰胺基团的喹唑啉酮衍生物，最高收率达81%。该方法在温和条件下制备氨酰稠合喹唑啉酮衍生物，具有产率高、底物兼容性广、原子经济性高等优点。
• Persulfate-Promoted Carbamoylation/Cyclization of Alkenes: Synthesis of Amide-Containing Quinazolinones
  作者：Jia-Jun Tang、Meng-Yang Zhao、Ying-Jun Lin、Li-Hua Yang、Long-Yong Xie

  DOI：10.3390/molecules29050997

  日期：——

  The incorporation of amide groups into biologically active molecules has been proven to be an efficient strategy for drug design and discovery. In this study, we present a simple and practical method for the synthesis of amide-containing quinazolin-4(3H)-ones under transition-metal-free conditions. This is achieved through a carbamoyl-radical-triggered cascade cyclization of N3-alkenyl-tethered quinazolinones

  将酰胺基团掺入生物活性分子已被证明是药物设计和发现的有效策略。在这项研究中，我们提出了一种在无过渡金属条件下合成含酰胺的喹唑啉-4(3H)-酮的简单实用的方法。这是通过氨基甲酰基自由基触发的 N3-烯基连接的喹唑啉酮级联环化来实现的。值得注意的是，氨基甲酰基自由基是在 (NH4)2S2O8 存在下草酰胺酸的氧化脱羧过程中原位产生的。