3-甲基-2-苯氨基苯甲酸 | 40961-11-3

• 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: 3-甲基-2-苯氨基苯甲酸
• 英文名称: N-phenyl-3-methylanthranilic acid
• 英文别名: 3-Methyl-N-phenyl-anthranilsaeure；N-Phenyl-2-amino-3-toluolsaeure；3-Methyl-2-(phenylamino)benzoic acid；2-anilino-3-methylbenzoic acid
• CAS: 40961-11-3
• 化学式: C₁₄H₁₃NO₂
• 分子量: 227.263
• InChiKey: VUDSJNWASUESGF-UHFFFAOYSA-N

物化性质

• 熔点：
  189 °C
• 沸点：
  384.4±30.0 °C(Predicted)
• 密度：
  1.233±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 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：

  3-甲基-2-苯氨基苯甲酸 在 lithium aluminium tetrahydride 、 sodium hydride 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.25h， 生成 3-methyl-2-(methyl(phenyl)amino)benzaldehyde
  参考文献：
  名称：

  Sc(OTf)₃-Catalyzed Dehydrogenative Cyclization for Synthesis of N-Methylacridones

  摘要：

  A novel method has been developed for the synthesis of substituted N-methylacridones from 2-(N-methyl-N-phenylamino)benzaldehydes via dehydrogenative cyclization. This transformation involves two primary processes: the aldehyde first coordinates with Sc(OTf)(3) and induces the aromatic electrophilic substitution (SEAr) reaction to form the active intermediate N-methyl-acridin-9-ol, which is then quickly oxidized in situ to afford the acridones. Furthermore, the procedure involved is both environmental friendly and atom efficient; H2O is the only byproduct in this reaction.

  DOI：

  10.1021/ol400371h
• 作为产物：
  描述：

  2-碘-3-甲基苯甲酸 、 苯胺 在 copper diacetate 、 sodium acetate 作用下， 以 水 为溶剂， 生成 3-甲基-2-苯氨基苯甲酸
  参考文献：
  名称：

  Sc(OTf)₃-Catalyzed Dehydrogenative Cyclization for Synthesis of N-Methylacridones

  摘要：

  A novel method has been developed for the synthesis of substituted N-methylacridones from 2-(N-methyl-N-phenylamino)benzaldehydes via dehydrogenative cyclization. This transformation involves two primary processes: the aldehyde first coordinates with Sc(OTf)(3) and induces the aromatic electrophilic substitution (SEAr) reaction to form the active intermediate N-methyl-acridin-9-ol, which is then quickly oxidized in situ to afford the acridones. Furthermore, the procedure involved is both environmental friendly and atom efficient; H2O is the only byproduct in this reaction.

  DOI：

  10.1021/ol400371h

文献信息

• New Methylenebisphenyl Compounds Useful in the Treatment of Inflammation
  申请人：Pelcman Benjamin

  公开号：US20100144872A1

  公开（公告）日：2010-06-10

  There is provided compounds of formula (I), wherein R x , R y , X 1 , X 2 , L 1 , L 2 , Y 1 and Y 2 have meanings given in the description, and pharmaceutically-acceptable salts thereof, which compounds are useful in the treatment of diseases in which inhibition of the activity of leukotriene C 4 synthase is desired and/or required, and particularly in the treatment of a respiratory disorder and/or inflammation.

  提供了式(I)的化合物，其中Rx、Ry、X1、X2、L1、L2、Y1和Y2的含义在说明中给出，以及其药学上可接受的盐。这些化合物在希望和/或需要抑制白三烯C4合酶活性的疾病治疗中非常有用，特别是在呼吸道疾病和/或炎症的治疗中。
• Conformational flexibility and substitution pattern lead to polymorphism of 3-methyl-2-(phenylamino)benzoic acid
  作者：Yang Tao、Xiaoting Liu、Yunping Zhoujin、Panpan Zhou、Sean Parkin、Tonglei Li、Ju Guo、Faquan Yu、Sihui Long

  DOI：10.1039/d2ce00126h

  日期：——

  single-crystal X-ray diffraction, powder X-ray diffraction (PXRD), and FT-IR. The polymorphs of compound 5 were investigated in detail experimentally and theoretically. Conformational scan provided insight into the origin of polymorphism of 5. NBO calculations confirmed the composition and nature of sigma bond character of the two N-C bonds in 5. Hirshfeld analysis accounted for the major intermolecular interactions

  为了探究苯甲酸环上的取代对苯氨基苯甲酸多态性的影响，合成了五种 3-甲基-2-(苯氨基)苯甲酸 (MPABAs)。初步的多晶型筛选导致化合物 1-4 的一种形式，以及化合物 5 的三种形式和溶剂化物（5-I、5-II、5-III 和 5-S）。这一观察结果类似于结构相关的化合物，苯甲酸环上没有取代。所有晶型均通过单晶 X 射线衍射、粉末 X 射线衍射 (PXRD) 和 FT-IR 进行了表征。对化合物5的多晶型进行了详细的实验和理论研究。构象扫描提供了对 5 多态性起源的深入了解。 NBO 计算证实了 5 中两个 NC 键的 sigma 键特征的组成和性质。Hirshfeld 分析解释了有助于晶体整体稳定性的主要分子间相互作用。很明显，构象灵活性本身不会导致多态性，取代位置和模式是研究化合物中多态性的真正决定因素。
• Regioselective Copper-Catalyzed Amination of Bromobenzoic Acids Using Aliphatic and Aromatic Amines
  作者：Christian Wolf、Shuanglong Liu、Xuefeng Mei、Adam T. August、Michael D. Casimir

  DOI：10.1021/jo060034a

  日期：2006.4.1

  A chemo- and regioselective copper-catalyzed cross-coupling procedure for amination of 2-bromobenzoic acids is described. The method eliminates the need for acid protection and produces N-aryl and N-alkyl anthranilic acid derivatives in up to 99% yield. N-(1-Pyrene)anthranilic acid has been employed in metal ion-selective fluorosensing. Titration experiments showed that this pyrene-derived amino acid forms an equimolar complex with Hg(II) in water resulting in selective fluorescence quenching even in the presence of other metal ions such as Zn(II) and Cd(II).
• KIMURA, MICHIO;OKABAYASHI, ICHIZO;KATO, AKIRA, CHEM. AND PHARM. BULL., 37,(1989) N, C. 697-701
  作者：KIMURA, MICHIO、OKABAYASHI, ICHIZO、KATO, AKIRA

  DOI：——

  日期：——
• PHENYLETHYLPYRIDINE DERIVATIVES AS PDE4-INHIBITORS AND MUSCARINIC RECEPTOR ANTAGONISTS
  申请人：Chiesi Farmaceutici S.p.A.

  公开号：EP2928880B1

  公开（公告）日：2018-02-14