2-(甲基氨基)苯甲酸异丙酯 | 99985-64-5

• 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: 2-(甲基氨基)苯甲酸异丙酯
• 英文名称: isopropyl N-methylanthranilate
• 英文别名: Propan-2-yl 2-(methylamino)benzoate
• CAS: 99985-64-5
• 化学式: C₁₁H₁₅NO₂
• mdl: MFCD12144174
• 分子量: 193.246
• InChiKey: OBKVPPPSOAFJDS-UHFFFAOYSA-N

物化性质

• 保留指数：
  1491

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2922499990

反应信息

• 作为反应物：
  描述：

  2-(甲基氨基)苯甲酸异丙酯 在 盐酸 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 0.5h， 以70%的产率得到isopropyl N-methyl-N-nitrosoanthranilate
  参考文献：
  名称：

  一种利用快速真空热解产生 7-氨基苯酞的 N-亚硝基邻氨基苯甲酸酯热解的新途径

  摘要：

  N-甲基-N-亚硝基邻氨基苯甲酸甲酯的快速真空热解导致一氧化氮的消除和形成的N-自由基歧化为7-(甲氨基)苯酞和N-甲基邻氨基苯甲酸甲酯。发现这种转化是一种方便的、无溶剂的制备 7-(甲氨基)苯酞的方法。还研究了通过N-苄基-N-甲基邻氨基苯甲酸酯热解的替代途径。

  DOI：

  10.1039/d0ob01946a
• 作为产物：
  描述：

  methyl N-methyl-N-nitrosoanthranilate 在 isopropoxide 作用下， 生成 2-(甲基氨基)苯甲酸异丙酯
  参考文献：
  名称：

  一种利用快速真空热解产生 7-氨基苯酞的 N-亚硝基邻氨基苯甲酸酯热解的新途径

  摘要：

  N-甲基-N-亚硝基邻氨基苯甲酸甲酯的快速真空热解导致一氧化氮的消除和形成的N-自由基歧化为7-(甲氨基)苯酞和N-甲基邻氨基苯甲酸甲酯。发现这种转化是一种方便的、无溶剂的制备 7-(甲氨基)苯酞的方法。还研究了通过N-苄基-N-甲基邻氨基苯甲酸酯热解的替代途径。

  DOI：

  10.1039/d0ob01946a

文献信息

• Dembele, Albert; Deshayes, Henri; Pete, Jean-Pierre, Bulletin de la Societe Chimique de France, 1988, # 4, p. 671 - 680
  作者：Dembele, Albert、Deshayes, Henri、Pete, Jean-Pierre

  DOI：——

  日期：——
• Palladium-Catalyzed Oxidative Carbonylation of Aromatic C–H Bonds of <i>N</i>-Alkylanilines with CO and Alcohols for the Synthesis of <i>o</i>-Aminobenzoates
  作者：Ming Chen、Zhi-Hui Ren、Yao-Yu Wang、Zheng-Hui Guan

  DOI：10.1021/jo502581p

  日期：2015.1.16

  A Pd(II)-catalyzed CH monocarbonylation of N-alkylanilines for the synthesis of o-aminobenzoates has been developed. Various aliphatic alcohols and phenol were tolerated in the reaction to afford the corresponding o-aminobenzoates in good yields under mild balloon pressure of CO.
• Isatoic Anhydride. IV. Reactions with Various Nucleophiles
  作者：ROGER P. STAIGER、EMERY B. MILLER

  DOI：10.1021/jo01091a013

  日期：1959.9
• Identification of a new antinociceptive alkaloid isopropyl N-methylanthranilate from the essential oil of Choisya ternata Kunth
  作者：Niko S. Radulović、Ana B. Miltojević、Michael McDermott、Steve Waldren、John Adrian Parnell、Mariana Martins Gomes Pinheiro、Patricia Dias Fernandes、Fabio de Sousa Menezes

  DOI：10.1016/j.jep.2011.03.035

  日期：2011.6

  Ethnopharmacological relevance: Mexican people employed infusion of leaves of Choisya ternata Kunth for their antispasmodic and "simulative properties".Aim of the study: In the present study the detailed GC and GC-MS analyses of the essential oil of Choisya ternata Kunth (Rutaceae) were performed. The presence of a minor constituent isopropyl N-methylanthranilate (1) was revealed among other identified volatiles. A synthesis of 1 was undertaken in order to corroborate this find and obtain gram quantities that would allow the testing of its biological activity (peripheral and central antinociceptive activity).Materials and methods: The oils were investigated by GC and GC-MS. Synthesized compounds were spectrally characterized (UV-Vis, IR, 1D and 2D NMR, MS). The obtained synthetic samples of compounds were assayed for peripheral and central antinociceptive activity in two models (effects on acetic acid induced writhing in mice and the hot plate test for nociception).Results: Detailed GC and GC-MS analyses of the essential oil of Choisya ternata Kunth (Rutaceae) among 157 other identified volatiles revealed the presence of a minor constituent isopropyl N-methylanthranilate (1). Compound 1, named ternanthranin, is therefore detected as a natural product for the first time with a very restricted occurrence (samples of several citrus oils were screened for the presence of 1). The antinociceptive activities were assayed for ternanthranin, the two other synthetic analogs, methyl and propyl N-methylanthranilate, as well as the essential oil and the crude ethanol extract of the leaves. The results clearly demonstrate a very high (even significant at 0.3 mg/kg) dose dependent activity for the anthranilates (and the extracts). Isopropyl N-methylanthranilate showed the highest, while methyl N-methylanthranilate showed the lowest activity (with the methyl ester at 3 mg/kg still better than acetylsalicylic acid, at 200 mg/kg, in the first, or comparable with morphine, at 5 mg/kg, in the second test).Conclusion: This study once again revealed that detailed investigations of plant species with ethnopharmacologically documented activity may yield new natural compounds a new alkaloid (ternanthranin), a volatile simple anthranilate that can be considered responsible for the antinociceptive activity of the crude plant extracts. (C) 2011 Elsevier Ireland Ltd. All rights reserved.
• A novel pathway for the thermolysis of <i>N</i>-nitrosoanthranilates using flash vacuum pyrolysis leading to 7-aminophthalides
  作者：Dragan Zlatković、Doris Dallinger、C. Oliver Kappe

  DOI：10.1039/d0ob01946a

  日期：——

  Flash vacuum pyrolysis of methyl N-methyl-N-nitrosoanthranilate leads to elimination of nitric oxide and disproportionation of the formed N-radical to 7-(methylamino)phthalide and methyl N-methylanthranilate. This transformation was found to be a convenient, solvent-free method for the preparation of 7-(methylamino)phthalides. An alternative route through pyrolysis of N-benzyl-N-methyl anthranilates

  N-甲基-N-亚硝基邻氨基苯甲酸甲酯的快速真空热解导致一氧化氮的消除和形成的N-自由基歧化为7-(甲氨基)苯酞和N-甲基邻氨基苯甲酸甲酯。发现这种转化是一种方便的、无溶剂的制备 7-(甲氨基)苯酞的方法。还研究了通过N-苄基-N-甲基邻氨基苯甲酸酯热解的替代途径。