N-(4-氯苯基)邻氨基苯甲酸甲酯 | 23868-23-7

• 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: N-(4-氯苯基)邻氨基苯甲酸甲酯
• 英文名称: 2-(p-Chlor-phenylamino)-benzoesaeure-methylester
• 英文别名: N-(4-chlorophenyl)anthranilic acid methyl ester；2-(4-chloro-anilino)-benzoic acid methyl ester；Methyl 2-(4-chloroanilino)benzoate；methyl 2-(4-chloroanilino)benzoate
• CAS: 23868-23-7
• 化学式: C₁₄H₁₂ClNO₂
• 分子量: 261.708
• InChiKey: CACDDPVFQVAPPS-UHFFFAOYSA-N

物化性质

• 沸点：
  378.5±27.0 °C(Predicted)
• 密度：
  1.274±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(4-氯苯基)邻氨基苯甲酸甲酯 在 tetraphosphorus decasulfide 作用下， 以 xylene 为溶剂， 生成 1-(p-Chlor-phenyl)-2-methoxy-3,1,2P(V)-benzothiazaphosphorin-2,4-dithion
  参考文献：
  名称：

  Legrand,L.; Lozac'h,N., Bulletin de la Societe Chimique de France, 1969, p. 1173 - 1182

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(三氟甲基磺酰氧基)苯甲酸甲酯 、 对氯苯胺 在 palladium diacetate 、 caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 甲苯 为溶剂， 以96%的产率得到N-(4-氯苯基)邻氨基苯甲酸甲酯
  参考文献：
  名称：

  Development of Potent and Selective Inhibitors of Aldo–Keto Reductase 1C3 (Type 5 17β-Hydroxysteroid Dehydrogenase) Based on N-Phenyl-Aminobenzoates and Their Structure–Activity Relationships

  摘要：

  Aldo-keto reductase 1C3 (AKR1C3; type 5 17 beta-hydroxysteroid dehydrogenase) is overexpressed in castration resistant prostate cancer (CRPC) and is implicated in the intratumoral biosynthesis of testosterone and 5 alpha-dihydrotestosterone. Selective AKR1C3 inhibitors are required because compounds should not inhibit the highly related AKR1C1 and AKR1C2 isoforms which are involved in the inactivation of Sa-dihydrotestosterone. NSAIDs, N-phenylanthranilates in particular, are potent but nonselective AKR1C3 inhibitors. Using flufenamic acid, 2-{[3-(trifluoromethyl)phenyl]amino}benzoic acid, as lead compound, five classes of structural analogues were synthesized and evaluated for AKR1C3 inhibitory potency and selectivity. Structure-activity relationship (SAR) studies revealed that a meta-carboxylic acid group relative to the amine conferred pronounced AKR1C3 selectivity without loss of potency, while electron withdrawing groups on the phenylamino B-ring were optimal for AKR1C3 inhibition. Lead compounds did not inhibit COX-1 or COX-2 but blocked the AKR1C3 mediated production of testosterone in LNCaP-AKR1C3 cells. These compounds offer promising leads toward new therapeutics for CRPC.

  DOI：

  10.1021/jm201547v

文献信息

• Compounds for electronic devices
  申请人：Parham Amir Hossain

  公开号：US10177312B2

  公开（公告）日：2019-01-08

  The present application relates to a compound of a formula (I), to the use of this compound in an electronic device, and to an electronic device comprising one or more compounds of the formula (I). The invention furthermore relates to the preparation of the compound of the formula (I) and to a formulation comprising one or more compounds of the formula (I).

  本申请涉及一种式 (I) 化合物、该化合物在电子设备中的用途以及包含一种或多种式 (I) 化合物的电子设备。此外，本发明还涉及式（I）化合物的制备方法以及包含一种或多种式（I）化合物的配方。
• Pd-Catalyzed Decarbonylative sp2 C–H Arylation: Construction of Five- and Six-Membered (Hetero)Cyclic Compounds
  作者：Shanshan Zhang、Mengjie Cen、Chenglong Li、Long Liu、Tianzeng Huang、Tieqiao Chen

  DOI：10.1021/acs.orglett.4c01412

  日期：2024.6.7

  The cyclic compounds have wide applications in the design and synthesis of drugs and materials; thus, their efficient construction attracts much attention from the synthetic community. In this letter, we report an efficient method for preparing cyclic compounds starting from the readily available carboxylic acids. This reaction takes place through intramolecular decarbonylative sp2 C–H arylation, enabling

  环状化合物在药物和材料的设计与合成中具有广泛的应用；因此，它们的高效构建引起了合成界的广泛关注。在这封信中，我们报告了一种从容易获得的羧酸出发制备环状化合物的有效方法。该反应通过分子内脱羰sp 2 C–H 芳基化发生，从而能够有效合成各种五元和六元环状化合物。在该反应条件下可以生成碳环和杂环。此外，该反应具有底物范围广、官能团耐受性高等特点。放大实验也显示了其在有机合成中的实用性。这些实验结果表明该反应将在合成界得到广泛的应用。
• VERBINDUNGEN FÜR ELEKTRONISCHE VORRICHTUNGEN
  申请人：Merck Patent GmbH

  公开号：EP2705550B1

  公开（公告）日：2017-07-05
• COMPOUNDS FOR ELECTRONIC DEVICES
  申请人：Parham Amir Hossain

  公开号：US20140070146A1

  公开（公告）日：2014-03-13

  The present application relates to a compound of a formula (I), to the use of this compound in an electronic device, and to an electronic device comprising one or more compounds of the formula (I). The invention furthermore relates to the preparation of the compound of the formula (I) and to a formulation comprising one or more compounds of the formula (I).
• [DE] VERBINDUNGEN FÜR ELEKTRONISCHE VORRICHTUNGEN<br/>[EN] COMPOUNDS FOR ELECTRONIC DEVICES<br/>[FR] COMPOSÉS POUR DISPOSITIFS ÉLECTRONIQUES
  申请人：MERCK PATENT GMBH

  公开号：WO2012149999A1

  公开（公告）日：2012-11-08

  Die vorliegende Anmeldung betrifft eine Verbindung einer Formel (I), die Verwendung dieser Verbindung in einer elektronischen Vorrichtung, sowie eine elektronische Vorrichtung, enthaltend eine oder mehrere Verbindungen der Formel (I). Weiterhin betrifft die Erfindung die Herstellung der Verbindung der Formel (I) sowie eine Formulierung enthaltend eine oder mehrere Verbindungen der Formel (I).