2-[(4-苄氧基苯基氨基)-亚甲基]-丙二酸二乙酯 | 35957-44-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 2-[(4-苄氧基苯基氨基)-亚甲基]-丙二酸二乙酯
• 英文名称: diethyl 2-(((4-(benzyloxy)phenyl)amino)methylene)malonate
• 英文别名: Diethyl 2-[(4-phenylmethoxyanilino)methylidene]propanedioate
• CAS: 35957-44-9
• 化学式: C₂₁H₂₃NO₅
• 分子量: 369.417
• InChiKey: YMJDJFCXXVBKRB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-[(4-苄氧基苯基氨基)-亚甲基]-丙二酸二乙酯 在 乙二胺 作用下， 以 乙醇 为溶剂， 反应 1.3h， 以95%的产率得到4-苄氧基苯胺
  参考文献：
  名称：

  2,2-双（乙氧羰基）乙烯基（BECV）作为多功能胺的保护基团，用于选择性官能团转化

  摘要：

  在室温下，存在潜在干扰官能团（例如OH，SH，COOH以及其他NH 2基团）的情况下，将2，2-双（乙氧羰基）乙烯基（BECV）基团用于胺的选择性保护。在BECV基团存在的情况下，可以选择性地进行一些官能团转化，例如酯化，O-烷基化，O-酰化，N-烷基化，N-酰化，S-烷基化。在室温下，使用乙二胺可在短时间内实现BECV基团的选择性脱保护，而其他一些官能团（如苯甲酸酯，脂族酯，酰胺和醚）则保持完整。BECV基团显示出对常见保护基（如Fmoc，Cbz和Boc）的正交稳定性。

  DOI：

  10.1002/chem.200902054
• 作为产物：
  描述：

  4-苯甲氧基苯胺盐酸盐 在 sodium hydroxide 作用下， 以 乙醚 、 水 为溶剂， 反应 1.5h， 生成 2-[(4-苄氧基苯基氨基)-亚甲基]-丙二酸二乙酯
  参考文献：
  名称：

  [EN] CARBAMATE LINKED MACROLIDES USEFUL FOR THE TREATMENT OF MICROBIAL INFECTIONS
  [FR] MACROLIDES A LIAISON CARBAMATE UTILISES DANS LE TRAITEMENT DES INFECTIONS MICROBIENNES

  摘要：

  本发明涉及在式(I)的4'位置被取代的14-或15-元大环内酯及其药学上可接受的衍生物，以及它们的制备过程和在人体或动物体内治疗或预防全身或局部微生物感染中的用途。

  公开号：

  WO2005108413A1

文献信息

• Structure-guided optimization of quinoline inhibitors of Plasmodium N-myristoyltransferase
  作者：Victor Goncalves、James A. Brannigan、Alice Laporte、Andrew S. Bell、Shirley M. Roberts、Anthony J. Wilkinson、Robin J. Leatherbarrow、Edward W. Tate

  DOI：10.1039/c6md00531d

  日期：——

  Quinolines with balanced activities against bothPlasmodium vivaxandPlasmodium falciparum N-myristoyltransferase were identified.

  喹啉类化合物对间日疟原虫和恶性疟原虫N-肌醇化酰基转移酶均具有平衡的活性。
• Lewis Acid Mediated Selective Monohydrolysis of Geminal Diesters: Synthesis of Functionalized Malonic Acid Half Esters
  作者：Andivelu Ilangovan、Rajendran Kumar、Mahabir Kaushik

  DOI：10.1055/s-0031-1290449

  日期：2012.9

  Geminal diesters, N-alkyl/aryl-2,2-bis(ethoxycarbonyl)vinylamines, were found to undergo selective hydrolysis in the presence of BF3·OEt2 at room temperature to give the corresponding half esters. Neighboring group participation by nitrogen in the hydrolysis was observed. This method is useful for the preparation of highly functionalized malonic acid half esters.

  发现孪生二酯，N-烷基/芳基-2,2-双(乙氧基羰基)乙烯基胺，在BF3·OEt2存在下在室温下经历选择性水解，得到相应的半酯。观察到氮参与水解的相邻基团。该方法可用于制备高度官能化的丙二酸半酯。
• Ethene derivatives
  申请人：MAY & BAKER LIMITED

  公开号：EP0174832A2

  公开（公告）日：1986-03-19

  Ethene derivatives of the general formula: wherein R5 represents a heterocyclyl group, containing 1, 2 or 3 rings and one or more heteroatoms selected from nitrogen, oxygen, sulphur and selenium atoms, which is unsubstituted or substituted by one or more substituents R8 [which may be the same or different and each represents a halogen atom or an amino, carboxy, cyano, nitro, hydroxy, oxo, formyl, trifluoromethyl, aryl, aryloxy, arylthio, benzyloxycarbonylamino, sulphamoyl, tetrazol-5-yl, carbamoyl, thiocarbamoyl, arylcarbamoyl or aroyl group, or a straight-or branched-chain alkyl group containing from 1 to 10 carbon atoms, or a straight- or branched-chain alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, alkylsulphamoyl, arylalkyl or arylalkoxy group containing from 1 to 10 carbon atoms in the alkyl moiety, a straight- or branched-chain alkanoyl, alkoxycarbonyl, alkoxycarbonylamino, alkylcarbamoyl or alkanoylamino group containing from 2 to 6 carbon atoms, an N-benzyloxycarbonyl-N-alkylamino group wherein the alkylamino moiety is straight- or branched-chain and contains from 1 to 6 carbon atoms, or a dialkylsulphamoyl, dialkylamino or dialkylcarbamoyl group wherein the alkyl moieties may be straight or branched and may each contain from 1 to 6 carbon atoms and may be linked together to form a ring, or a group of the formula -CR4=CR2R3, or an aryl group which is unsubstituted or substituted by one or more substituents RS (as hereinbefore defined), or a heterocyclylalkyl or arylalkyl group wherein the heterocyclyl or aryl moiety is as hereinbefore defined and the alkyl moiety is straight- or branched-chain and contains 1 or 2 carbons atoms, and R1 represents a group of the general formula: wherein R6 represents a hydrogen atom or a straight- or branched-chain alkyl group containing from 1 to 6 carbon atoms which may be substituted by one or more substituents RS (as hereinbefore defined) or an aryl group which may be substituted by one or more substituents R8 (as hereinbefore defined), or R5 represents a quinonoidal group R7 derived from a nitrogen-containing heterocyclyl group within the definition of R5 as hereinbefore defined, bearing on said ring-nitrogen atom a substituent selected from straight- and branched-chain alkyl groups containing from 1 to 6 carbon atoms which may be substituted by one or more substituents RS (as hereinbefore defined), and aryl groups which may be substituted by one or more substituents RS (as hereinbefore defined), and R1 represents an atom =N-, R4 represents a hydrogen atom or a straight- or branched-chain alkoxy or alkylthio group containing from 1 to 6 carbon atoms, a trifluoromethyl group or a straight- or branched-chain alkyl group containing from 1 to 6 carbon atoms which may be substituted by one or more substituents R8 (as hereinbefore defined), or an aryl group which may be substituted by one or more substituents R8 (as hereinbefore defined), R2 represents a cyano or formyl group, a straight- or branched-chain alkoxycarbonyl or alkylsulphonyl group containing up to 6 carbons, or a dialkylcarbamoyl or dialkylthiocarbamoyl group wherein the alkyl groups may be the same or different and each may be straight or branched and each contains from 1 to 6 carbon atoms, or an aryloxycarbonyl, arylsulphinyl or arylsulphonyl group wherein the aryl moiety may be substituted by one or more substituents R8 (as hereinbefore defined), R3 represents a group within the definition of R2 or a hydrogen atom or a nitro group or an aryl or aroyl group which may be substituted by one or more substituents R8 (as hereinbefore defined) or a straight- or branched-chain alkanoyl group containing up to 6 carbon atoms, and m and n each represents 1 or 2, and pharmaceutically acceptable salts thereof, with the provisos that the following classes of compounds are excluded:- (i) compounds of formula I wherein R5 represents a pyridyl group which is unsubstituted or substituted by one or more substituents R9 which may be the same or different and each represents a group within the definition of Re other than oxo, straight- or branched-chain alkyl containing from 7 to 10 carbon atoms, straight- or branched-chain alkoxy, alkylthio, alkylsulphonyl, alkylamino, alkylsulphamoyl or arylalkyl containing from 7 to 10 carbon atoms in the alkyl moiety, straight- or branched-chain alkylsulphinyl or arylalkoxy containing from 1 to 10 carbon atoms in the alkyl moiety, or a group -CR4=CR2R3 as hereinbefore defined, R2 and R3 may be the same or different and each represents a phenylsulphonyl group which may be unsubstituted or substituted by one or more substituents R9 (as hereinbefore defined), R' represents a group of formula II, R4 and R6 represent hydrogen atoms and m and n both represent 1; (ii) compounds of formula I wherein R5 represents a 5-halogenopyrid-2-yl group, R2 and R3 both represent cyano groups, R1 represents a group of formula II, R4 and R° represent hydrogen atoms and m and n both represent 1; and (iii) compounds of formula I wherein R5 represents a 1,2,4-triazolo[4,8-a]-quinoline group which is unsubstituted or substituted by one or more substituents R10 which may be the same or different and each represents a group within the definition of R9 or a straight- or branched-chain alkylsulphinyl group containing from 1 to 6 carbon atoms, R2 and R3 may be the same or different and each represents a cyano group, a straight- or branched-chain alkoxycarbonyl group containing from 2 to 6 carbon atoms, or a phenylsulphonyl group which may be unsubstituted or substituted by one or more substituents R10 (as hereinbefore defined), R' represents a group of formula II, R4 and R6 represent hydrogen atoms and m and n both represent 1, possess useful pharmacological properties.

  以下是对文本的中文翻译： **丙烯衍生物的通式**： 其中，R5代表一个杂环基，包含1、2或3个环，并且含有1个或多个选自氮、氧、硫和硒原子的杂原子，该杂环基可以是未取代的，或被一个或多个R8取代基取代（R8可以相同或不同，每个R8代表一个卤素原子；或者一个氨基、羧基、氰基、硝基、羟基、羰基、甲酰基、三氟甲基、芳基、芳氧基、芳硫基、苄氧羰基氨基、硫脲基、5-四唑基、羰基氨基、硫代羰基氨基、芳基羰基氨基或芳酰基；或者一个直链或支链烷基，含有1至10个碳原子；或者一个直链或支链烷氧基、烷硫基、烷亚砜基、烷砜基、烷氨基、烷硫脲基、芳基烷基或芳基烷氧基，其中烷基部分含有1至10个碳原子；或者一个直链或支链烷酰基、烷氧基羰基、烷氧基羰基氨基、烷基羰基氨基或烷酰基氨基，含有2至6个碳原子；或者一个N-苄氧羰基-N-烷基氨基，其中烷基氨基部分为直链或支链，含有1至6个碳原子；或者一个二烷基硫脲基、二烷基氨基或二烷基羰基氨基，其中烷基部分可以为直链或支链，每个烷基部分含有1至6个碳原子，且烷基部分可以彼此连接形成一个环；或者一个通式为-CR4=CR2R3的基团；或者一个未取代的芳基，或被一个或多个R8取代基取代的芳基；或者一个杂环基烷基或芳基烷基，其中杂环基或芳基部分如前所定义，烷基部分为直链或支链，含有1或2个碳原子）。 R1代表一个通式为的基团： 其中，R6代表一个氢原子；或一个直链或支链烷基，含有1至6个碳原子，该烷基可以被一个或多个R8取代基取代（如前所定义）；或一个芳基，可以被一个或多个R8取代基取代（如前所定义）。 此外，R5还可以代表一个由含氮杂环基衍生而来的醌状基团R7，该杂环基如前所定义的R5，其中环氮原子上取代有一个选自以下的基团：直链或支链烷基，含有1至6个碳原子，该烷基可以被一个或多个R8取代基取代（如前所定义）；或一个芳基，可以被一个或多个R8取代基取代（如前所定义）。 R1代表一个=NH原子；R4代表一个氢原子，或一个直链或支链烷氧基、烷硫基，含有1至6个碳原子；或一个三氟甲基基团；或一个直链或支链烷基，含有1至6个碳原子，该烷基可以被一个或多个R8取代基取代（如前所定义）；或一个芳基，可以被一个或多个R8取代基取代（如前所定义）。 R2代表一个氰基或甲酰基；或一个直链或支链烷氧基羰基或烷硫基，含有不超过6个碳原子；或一个二烷基羰基氨基或二烷基硫代羰基氨基，其中两个烷基可以相同或不同，每个烷基为直链或支链，含有1至6个碳原子；或一个芳氧基羰基、芳硫基或芳硫基羰基，其中芳基部分可以被一个或多个R8取代基取代（如前所定义）。 R3代表一个与R2定义范围内的基团，或一个氢原子；或一个硝基；或一个芳基；或一个芳酰基，可以被一个或多个R8取代基取代（如前所定义）；或一个直链或支链烷酰基，含有不超过6个碳原子。 m和n各自代表1或2。 除以下化合物类别外，上述结构及其药学上可接受的盐类具有有用的药理学性质： (i) 通式为I的化合物，其中R5代表一个吡啶基，该吡啶基可以是未取代的，或被一个或多个R9取代基取代，R9可以相同或不同，每个R9代表一个基团，其定义范围包括：R8（但不包括氧代基、直链或支链烷基，含有7至10个碳原子；直链或支链烷氧基、烷硫基、烷硫基、烷氨基、烷硫脲基、或芳基烷基，其中烷基部分含有7至10个碳原子；直链或支链烷亚砜基，或芳基烷氧基，其中烷基部分含有1至10个碳原子）；或一个如前所定义的-CR4=CR2R3基团。其中，R2和R3可以相同或不同，各自代表一个苯硫基，可以是未取代的，或被一个或多个R9取代基取代（如前所定义）。R’代表一个通式II的基团。R4和R6代表氢原子，m和n均为1。 (ii) 通式为I的化合物，其中R5代表一个5-卤素取代吡啶-2-基，R2和R3均为氰基，R1代表一个通式II的基团，R4和R°代表氢原子，m和n均为1。 (iii) 通式为I的化合物，其中R5代表一个1,2,4-三唑[4,8-a]-喹啉基，该基团可以是未取代的，或被一个或多个R10取代基取代，R10可以相同或不同，每个R10代表一个基团，其定义范围包括：R9（如前所定义），或一个直链或支链烷亚砜基，含有1至6个碳原子。R2和R3可以相同或不同，各自代表一个氰基、一个直链或支链烷氧基羰基（含有2至6个碳原子），或一个苯硫基，可以是未取代的，或被一个或多个R10取代基取代（如前所定义）。R’代表一个通式II的基团。R4和R6代表氢原子，m和n均为1。 上述化合物在排除了特定结构后，具有有用的药理学性质。
• Quinolinonyl Non-Diketo Acid Derivatives as Inhibitors of HIV-1 Ribonuclease H and Polymerase Functions of Reverse Transcriptase
  作者：Antonella Messore、Angela Corona、Valentina Noemi Madia、Francesco Saccoliti、Valeria Tudino、Alessandro De Leo、Davide Ialongo、Luigi Scipione、Daniela De Vita、Giorgio Amendola、Ettore Novellino、Sandro Cosconati、Mathieu Métifiot、Marie-Line Andreola、Francesca Esposito、Nicole Grandi、Enzo Tramontano、Roberta Costi、Roberto Di Santo

  DOI：10.1021/acs.jmedchem.1c00535

  日期：2021.6.24
• Computer-Aided Molecular Modeling, Synthesis, and Biological Evaluation of 8-(Benzyloxy)-2-phenylpyrazolo[4,3-c]quinoline as a Novel Benzodiazepine Receptor Agonist Ligand
  作者：C. G. Wang、T. Langer、P. G. Kamath、Z.-Q. Gu、P. Skolnick、R. Ian Fryer

  DOI：10.1021/jm00006a014

  日期：1995.3

  Using computer-aided conformational analysis, based on molecular dynamics simulation, cluster analysis, and Monte Carlo techniques, we have designed and synthesized compounds in which a benzyloxy substituent has been incorporated into a series of pyrazoloquinoline benzodiazepine receptor (BZR) ligands, Earlier studies had shown that the benzyloxy group could act as part of the agonist pharmacophoric determinant in the beta-carboline ring system. Furthermore, the agonist beta-carboline had been correlated with a binding site orientation and volume fit for an agonist 6-phenylimidazobenzodiazepine carboxylate. The present study was undertaken to determine whether the benzyloxy substituent could be used as an agonist pharmacophoric descriptor for the phenylpyrazolo[4,3-c]quinolin-3-one BZR ligands, The results of a determination of GABA shift ratios for the synthetic ligands indicate that 8-(benzyloxy)-2-phenylpyrazolo[4,3-c]quinolin-3-one can be predicted to be an agonist at the BZR.