4-methyl-2-(phenylamino)benzoic acid | 860530-40-1

• 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: 4-methyl-2-(phenylamino)benzoic acid
• 英文别名: 4-methyl-N-phenylanthranilic acid；2-anilino-4-methyl-benzoic acid；2-Anilino-4-methyl-benzoesaeure；2-Anilino-4-methylbenzoic acid
• CAS: 860530-40-1
• 化学式: C₁₄H₁₃NO₂
• 分子量: 227.263
• InChiKey: MKKSUNSQPRKIFW-UHFFFAOYSA-N

物化性质

• 沸点：
  397.4±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

反应信息

• 作为反应物：
  描述：

  4-methyl-2-(phenylamino)benzoic acid 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 C₁₅H₁₅NO
  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：

  苯胺 、 2-溴-4-甲基苯甲酸 在 copper(I) oxide 、 铜 、 potassium carbonate 作用下， 以 异戊醇 为溶剂， 生成 4-methyl-2-(phenylamino)benzoic acid
  参考文献：
  名称：

  2-苯乙烯基蒽的氮杂杂环芳烃衍生物的合成及光谱性质

  摘要：

  从3-硝基-2-萘醛和2-溴-4-甲基苯甲酸获得2-苯乙烯基蒽的新型氮杂杂芳族衍生物：2-苯乙烯基苯并[ g ]喹啉和3-苯乙烯基-cr啶。研究了新化合物的光谱性质。

  DOI：

  10.1007/s10593-013-1160-1

文献信息

• Studies on 4(1H)-Quinazolinones. 5. Synthesis and Antiinflammatory Activity of 4(1H)-Quinazolinone Derivatives
  作者：Ken-ichi Ozaki、Yoshihisa Yamada、Toyonari Oine、Tōru Ishizuka、Yoshio Iwasawa

  DOI：10.1021/jm50001a006

  日期：1985.5

  new 4(1H)-quinazolinones were synthesized and evaluated in the carrageenin-induced paw edema test. Most of the compounds were obtained by the cyclization of the appropriately substituted anthranilamides with acid chlorides, followed by further chemical transformation. Structure-activity data suggest that 2-isopropyl-1-phenyl-, 2-cyclopropyl-1-phenyl-, and 1-isopropyl-2-phenyl-4(1H)-quinazolinones afford

  合成了许多新的4（1H）-喹唑啉酮，并在角叉菜胶诱导的爪水肿试验中进行了评估。大多数化合物是通过将适当取代的邻氨基苯甲酰胺与酰氯环合，然后进一步化学转化而获得的。结构活性数据表明2-异丙基-1-苯基-，2-环丙基-1-苯基-和1-异丙基-2-苯基-4（1H）-喹唑啉酮具有最佳效价，卤素原子的存在为首选活动。肾上腺切除术不影响抗炎测试结果。1-异丙基-（2-氟苯基）-4-（1H）-喹唑啉酮（50）显示出兼顾功效和副作用的最佳结果。
• Synthesis and spectral properties of Azahetero-aromatic derivatives of 2-styrylanthracene
  作者：V. M. Lee、M. F. Budyka

  DOI：10.1007/s10593-013-1160-1

  日期：2013.1

  Novel azaheteroaromatic derivatives of 2-styrylanthracene: 2-styrylbenzo[g]quinoline and 3-styryl- acridine were obtained from 3-nitro-2-naphthaldehyde and 2-bromo-4-methylbenzoic acid. Spectral properties of the new compounds were studied.

  从3-硝基-2-萘醛和2-溴-4-甲基苯甲酸获得2-苯乙烯基蒽的新型氮杂杂芳族衍生物：2-苯乙烯基苯并[ g ]喹啉和3-苯乙烯基-cr啶。研究了新化合物的光谱性质。
• Synthesis of Quinazolinone-Fused Tetrahydroisoquinolines and Related Polycyclic Scaffolds by Iodine-Mediated sp³ C–H Amination
  作者：Manman Wang、Wenjun Ye、Nannan Sun、Wenquan Yu、Junbiao Chang

  DOI：10.1021/acs.joc.2c02509

  日期：2023.1.20

  This reaction does not use transition metals, has a broad substrate scope, and can be used on a gram scale. Under the optimal reaction conditions, a variety of quinazolinone-fused tetrahydroisoquinolines and derivatives of Rutaecarpine were synthesized from readily accessible compounds. The reaction proceeds well with crude 2-aminobenzamide derivatives, allowing for the synthesis of the products from

  碘介导的分子内 sp 3报道了从 2-氨基苯甲酰胺前体产生喹唑啉酮稠合多环骨架的 C-H 胺化反应。该反应不使用过渡金属，底物范围广，可在克级上使用。在最佳反应条件下，从容易获得的化合物合成了多种喹唑啉酮稠合四氢异喹啉和芸香碱衍生物。该反应与粗 2-氨基苯甲酰胺衍生物进行得很好，允许从简单的 2-氨基苯甲酸和四氢异喹啉合成产品，而无需纯化 2-氨基苯甲酰胺中间体。初步生物学实验已经确定了其中一些多环产品中的 Cereblon (CRBN) 抑制活性和相关的抗骨髓瘤药用特性。
• Preparation and Characterization of Thermochemiluminescent Acridine-Containing 1,2-Dioxetanes as Promising Ultrasensitive Labels in Bioanalysis
  作者：Massimo Di Fusco、Arianna Quintavalla、Claudio Trombini、Marco Lombardo、Aldo Roda、Massimo Guardigli、Mara Mirasoli

  DOI：10.1021/jo401683r

  日期：2013.11.15

  Thermochemiluminescence is the luminescence process in which a thermodynamically unstable molecule decomposes with light emission when heated above a threshold temperature. We recently reported the thermochemiluminescence properties of an acridine-containing 1,2-dioxetane, which emits at relatively low temperatures (i.e., below 100 degrees C). Herein, we explored the effect of the introduction of methyl substituents in the acridine system. The methyl group did not determine an excessive destabilization of 1,2-dioxetane ring nor significantly affect the general physical properties of the molecule. Monosubstituted methyl derivatives and a series of derivatives bearing several combinations of two, three, and four methyl groups were prepared. The rate of formation of 1,2-dioxetane derivatives 1b-k strongly depended on the methyl substitution pattern. All members of this library of mono-, di-, tri-, and tetramethyl-substituted derivatives were characterized in terms of photophysical and thermochemiluminescence properties. The introduction of methyl groups into the acridine ring caused a marked decrease in the activation energy of the thermochemiluminescent reaction. Tri- and tetramethyl-substituted acridones had the highest fluorescence quantum yields, in the range 0.48-0.52, and the corresponding 1,2-dioxetanes 1h and 1j showed in thermochemiluminescence imaging experiments limit of detection values more than ten times lower with respect to the unsubstituted derivative.
• Gleu; Nitzsche, Journal fur praktische Chemie (Leipzig 1954), 1939, vol. <2> 153, p. 200,213
  作者：Gleu、Nitzsche

  DOI：——

  日期：——