dimethyl 2-(phenylamino)terephthalate | 566155-74-6

• 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: dimethyl 2-(phenylamino)terephthalate
• 英文别名: Dimethyl 2-anilinobenzene-1,4-dicarboxylate
• CAS: 566155-74-6
• 化学式: C₁₆H₁₅NO₄
• 分子量: 285.299
• InChiKey: SBHNKIGYTHNEAR-UHFFFAOYSA-N

物化性质

• 沸点：
  424.9±35.0 °C(Predicted)
• 密度：
  1.233±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dimethyl 2-(phenylamino)terephthalate 在 lithium hydroxide 、 PPA 、 N,N-bis[2-oxo-3-oxazolidinyl]phosphorodiamidic chloride 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 9-oxo-N-[2-(pyridin-4-yl)propan-2-yl]-9,10-dihydroacridine-3-carboxamide
  参考文献：
  名称：

  Acridone-Based Inhibitors of Inosine 5‘-Monophosphate Dehydrogenase:  Discovery and SAR Leading to the Identification of N-(2-(6-(4-Ethylpiperazin-1-yl)pyridin-3-yl)propan-2-yl)-2- fluoro-9-oxo-9,10-dihydroacridine-3-carboxamide (BMS-566419)

  摘要：

  Inosine monophosphate dehydrogenase (IMPDH), a key enzyme in the de novo synthesis of guanosine nucleotides, catalyzes the irreversible nicotinamide-adenine dinucleotide dependent oxidation of inosine-5'-monophosphate to xanthosine-5'-monophosphate. Mycophenolate Mofetil (MMF), a prodrug of mycophenolic acid, has clinical utility for the treatment of transplant rejection based on its inhibition of IMPDH. The overall clinical benefit of MMF is limited by what is generally believed to be compound-based, dose-limiting gastrointestinal (GI) toxicity that is related to its specific pharmacokinetic characteristics. Thus, development of an IMPDH inhibitor with a novel structure and a different pharmacokinetic profile may reduce the likelihood of GI toxicity and allow for increased efficacy. This article will detail the discovery and SAR leading to a novel and potent acridone-based IMPDH inhibitor 4m and its efficacy and GI tolerability when administered orally in a rat adjuvant arthritis model.

  DOI：

  10.1021/jm070299x
• 作为产物：
  描述：

  2-硝基对苯二甲酸二甲酯 在 tris-(dibenzylideneacetone)dipalladium(0) 、 铁粉 、 potassium carbonate 、 氯化铵 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 6.5h， 生成 dimethyl 2-(phenylamino)terephthalate
  参考文献：
  名称：

  一种制备化合物UNC1215的方法

  摘要：

  本发明公开了一种制备化合物UNC1215的方法，属于药物化学合成技术领域，依次包括硝化反应、硝基还原反应、Buchwald反应、酯水解反应和缩合反应等步骤，本方法制备化合物UNC1215，反应总产率可达到67%，高于文献产率（60%）；本发明更改了合成路线，避免了封管反应，依次经过硝化反应、还原反应、Buchwald反应、水解反应及缩合反应，操作简便。

  公开号：

  CN104072403B

文献信息

• Metal-Free Synthesis of Secondary Arylamines: An Aliphatic-to-Aromatic Transformation
  作者：M. Teresa Barros、Suvendu S. Dey、Christopher D. Maycock

  DOI：10.1002/ejoc.201201263

  日期：2013.2

  An efficient method for the N-arylation of primary and some secondary amines using 2-halocyclohex-2-enones in an aliphatic-to-aromatic transformation in the presence of a substoichiometric amount of pTsOH has been developed.

  已经开发了一种在亚化学计量的 pTsOH 存在下使用 2-卤代环己-2-烯酮在脂肪族到芳香族转化中对伯胺和一些仲胺进行 N-芳基化的有效方法。
• Electroluminescent devices having conjugated arylamine polymers
  申请人：Zheng Shiying

  公开号：US20050186444A1

  公开（公告）日：2005-08-25

  An electroluminescent device, including a spaced-apart anode and cathode and an organic layer disposed between the spaced-apart anode and cathode and including a polymer having arylamine repeating unit moiety represented by formula wherein: Ar, Ar 1 , Ar 2 , Ar 3 , and Ar 4 are each individually arylof from 6 to 60 carbon atoms; or a heteroarylof from 4 to 60 carbons, or combinations thereof; or Ar 1 and Ar 2 , Ar 3 and Ar 4 , Ar 1 and Ar 4 , Ar 2 and Ar 4 are connected through a chemical bond; and X is a conjugated group having 2 to 60 carbon atoms.

  一种电致发光装置，包括相距一定距离的阳极和阴极以及位于相距一定距离的阳极和阴极之间的有机层，所述有机层包括聚合物，其具有由式表示的芳基胺重复单元基：其中：Ar，Ar1，Ar2，Ar3和Ar4分别为每个单独的芳基，其碳原子数为6至60个；或者是碳原子数为4至60个的杂芳基，或者是两者的组合；或者是通过化学键连接的Ar1和Ar2，Ar3和Ar4，Ar1和Ar4，Ar2和Ar4；X为具有2至60个碳原子的共轭基团。
• Acridone inhibitors of IMPDH enzyme
  申请人：——

  公开号：US20040053955A1

  公开（公告）日：2004-03-18

  Compounds having the formula (I), 1 wherein R 3 is selected from H, OH and NH 2 ; R 30 is selected from ═O and ═S; W is —C(═O)—, —S(═O)—, or —S(O) 2 —; or W may be —CH 2 — if X is —C(═O)—; X is selected from —CH 2 —, —N(R 4 )—, and —O—, except that when W is —CH 2 —, X is —C(═O)—; Y is a bond or —C(R 40 )(R 45 )—; Q is a linker; Z is optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heteroaryl, or heterocyclyl; and R 1 , R 2 , R 24 , and R 25 are as defined in the specification.

  化合物的化学式为（I），其中R3选自H，OH和NH2；R30选自═O和═S；W为—C(═O)—、—S(═O)—或—S(O)2—；如果X为—C(═O)—，则W可以为—CH2—；X选自—CH2—、—N(R4)—和—O—，但当W为—CH2—时，X为—C(═O)—；Y为键或—C(R40)(R45)—；Q为连接基；Z为可选的取代基的烷基、烯基、炔基、环烷基、芳基、杂芳基或杂环基；R1、R2、R24和R25如规范中所定义。
• ELECTROLUMINESCENT DEVICES HAVING CONJUGATED ARYLAMINE POLYMERS
  申请人：Zheng Shiying

  公开号：US20070278941A1

  公开（公告）日：2007-12-06

  An electroluminescent device, including a spaced-apart anode and cathode and an organic layer disposed between the spaced-apart anode and cathode and including a polymer having arylamine repeating unit moiety represented by formula wherein: Ar, Ar 1 , Ar 2 , Ar 3 , and Ar 4 are each individually arylof from 6 to 60 carbon atoms; or a heteroarylof from 4 to 60 carbons, or combinations thereof; or Ar 1 and Ar 2 , Ar 3 and Ar 4 , Ar 1 and Ar 4 , Ar 2 and Ar 4 are connected through a chemical bond; and X is a conjugated group having 2 to 60 carbon atoms.

  这是一种电致发光装置，包括间隔的阳极和阴极，以及位于间隔阳极和阴极之间的有机层。有机层包含聚合物，该聚合物具有由以下式表示的芳胺重复单元基团：其中，Ar、Ar1、Ar2、Ar3和Ar4分别是每个独立的芳基，其碳数为6至60个；或者是含有4至60个碳的杂芳基，或者是二者的组合；或者Ar1和Ar2、Ar3和Ar4、Ar1和Ar4、Ar2和Ar4通过化学键连接；而X是具有2至60个碳的共轭基团。
• Synthesis and evaluation of N-alkyl-9-aminoacridines with antibacterial activity
  作者：Adam R. Benoit、Charles Schiaffo、Christine E. Salomon、John R. Goodell、Hiroshi Hiasa、David M. Ferguson

  DOI：10.1016/j.bmcl.2014.05.037

  日期：2014.7

  A series of 9-alkylaminoacridines were synthesized and evaluated for activity against two strains of methicillin-resistant and one strain of methicillin-sensitive Staphylococcus aureus. Results are presented that show a clear structure activity relationship between the N-alkyl chain length and antibacterial activity with peak MIC99 values of 2-3 mu M for alkyl chains ranging from 10 to 14 carbons in length. Although prior work has linked the function of acridine-based compounds to intercalation and topoisomerase inhibition, the present results show that 9-alkylaminoacridines likely function as amphiphilic membrane-active disruptors potentially in a similar manner as quaternary ammonium antimicrobials. (C) 2014 Elsevier Ltd. All rights reserved.