(E)-methyl 4-(3,4-dimethoxyphenyl)-4-oxobut-2-enoate | 80937-21-9

• 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: (E)-methyl 4-(3,4-dimethoxyphenyl)-4-oxobut-2-enoate
• 英文别名: 4-oxo-4-(3.4-dimethoxy-phenyl)-trans-crotonic acid methyl ester；4-Oxo-4-(3.4-dimethoxy-phenyl)-trans-crotonsaeure-methylester；methyl 4-(3,4-dimethoxyphenyl)-4-oxo-2-butenoate；(E) methyl 4-(3,4-dimethoxyphenyl)-4-oxo-2-butenoate；Methyl (2E)-4-(3,4-Dimethoxyphenyl)-4-oxobut-2-enoate；methyl (E)-4-(3,4-dimethoxyphenyl)-4-oxobut-2-enoate
• CAS: 80937-21-9
• 化学式: C₁₃H₁₄O₅
• 分子量: 250.251
• InChiKey: HWFBZCHUTWPZIH-FNORWQNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-methyl 4-(3,4-dimethoxyphenyl)-4-oxobut-2-enoate 在 溴 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到methyl 2,3-dibromo-4-(3,4-dimethoxyphenyl)-4-oxobutanoate
  参考文献：
  名称：

  Tricyclic triazolobenzazepine derivatives, process for producing the same, and antiallergic

  摘要：

  提供了三环三唑苯并脂肪酸酯衍生物的形式或前药。根据本发明的化合物是由式(I)表示的那些化合物及其药理学上可接受的盐和溶剂化合物。这些化合物可用作抗过敏药物，并表现出优异的生物利用度。 其中R1代表氢、羟基、烷基或苯基烷基， R2、R3、R4和R5代表氢、卤素、可选择保护的羟基、甲酰基、可选择取代的烷基、烯基、烷氧基或类似物，以及 Q代表从以下组(i)到(iv)、卤素或烷氧基中选择的一个基团：

  公开号：

  US06372735B1
• 作为产物：
  描述：

  (E)-4-(3,4-二甲氧基苯基)-4-氧代-2-丁烯酸乙酯 生成 (E)-methyl 4-(3,4-dimethoxyphenyl)-4-oxobut-2-enoate
  参考文献：
  名称：

  Dave; Nargund, Journal of the University of Bombay, Science: Physical Sciences, Mathematics, Biological Sciences and Medicine, 1938, vol. 7/3, p. 191,194

  摘要：

  DOI：

文献信息

• Substituted 4-oxo-crotonic acid derivatives as a new class of protein kinase B (PknB) inhibitors: synthesis and SAR study
  作者：Changliang Xu、Xiaoguang Bai、Jian Xu、Jinfeng Ren、Yun Xing、Ziqiang Li、Juxian Wang、Jingjing Shi、Liyan Yu、Yucheng Wang

  DOI：10.1039/c6ra24953a

  日期：——

  Protein kinase B (PknB) is an essential serine/threonine protein kinase required for Mycobacterium tuberculosis (M. tb) cell division and cell-wall biosynthesis. A high throughput screen using PknB identified a (E)-4-oxo-crotonic acid inhibitor, named YH-8, which was used as a scaffold for SAR investigations. A significant improvement in enzyme affinity was achieved. The results indicated that the

  蛋白激酶B（PknB）是结核分枝杆菌（M. tb）细胞分裂和细胞壁生物合成所必需的丝氨酸/苏氨酸蛋白激酶。使用PknB进行的高通量筛选鉴定出一种名为YH-8的（E）-4-氧代巴豆酸抑制剂，该抑制剂被用作SAR研究的支架。实现了酶亲和力的显着改善。结果表明，α，β-不饱和酮骨架和“反式”构型对于对抗PknB的活性至关重要。而且具有芳基的化合物，特别是在苯环上具有吸电子取代基的化合物，其效能是YH-8的四倍。
• Design, synthesis, and bioevaluation of a novel class of (E)-4-oxo-crotonamide derivatives as potent antituberculosis agents
  作者：Jinfeng Ren、Jian Xu、Guoning Zhang、Changliang Xu、LiLi Zhao、XueFu You、Yucheng Wang、Yu Lu、Liyan Yu、Juxian Wang

  DOI：10.1016/j.bmcl.2019.01.001

  日期：2019.2

  A series of novel (E)-4-oxo-2-crotonamide derivatives were designed and synthesized to find potent antituberculosis agents. All the target compounds were evaluated for their in vitro activity against Mycobacterium tuberculosis H37Rv(MTB). Results reveal that 4-phenyl moiety at part A and short methyl group at part C were found to be favorable. Most of the derivatives displayed promising activity against

  设计并合成了一系列新颖的（E）-4-氧代-2-巴豆酰胺衍生物，以寻找有效的抗结核药。评价所有目标化合物的抗结核分枝杆菌H37Rv（MTB）的体外活性。结果表明，发现A部分的4-苯基部分和C部分的短甲基是有利的。大多数衍生物显示出对MTB有希望的活性，MIC为0.125至4 µg / mL。尤其是，发现化合物IIIa16对MTB的MIC最佳活性为0.125μg/ mL，对耐药性临床MTB分离株的MIC最佳为0.05-0.48μg/ mL。
• Synthesis of 3-Benzoyl Acrylates/Acrylamides via Dehydrogenation of 3-Benzoyl Propionates/Propionamides Using IBX/p-TsOH
  作者：Ziyuan Li、Yiyun Wang、Changhua Tang、Jinyi Xu、Xiaoming Wu、Hequan Yao

  DOI：10.1002/cjoc.201090225

  日期：——

  Dehydrogenation by IBX/p‐TsOH is applied to the conversion of 3‐benzoyl propionates/propionamides to 3‐benzoyl acrylates/acrylamides in moderate to excellent yields. The reaction time for the dehydrogenation of 3‐benzoyl propionamides was remarkably shorter than that for the dehydrogenation of esters.

  IBX / p- TsOH进行的脱氢用于将3-苯甲酰基丙酸酯/丙酰胺以中等至极好的收率转化为3-苯甲酰基丙烯酸酯/丙烯酰胺。3-苯甲酰基丙酰胺脱氢的反应时间明显短于酯脱氢的反应时间。
• Tricyclic triazolobenzazepine derivatives, process for producing the same, and antiallergic agents
  申请人：——

  公开号：US20020137739A1

  公开（公告）日：2002-09-26

  Tricyclic triazolobenzazepine derivatives in the form of a prodrug are provided. The compounds according to the present invention are those represented by formula (I) and pharmacologically acceptable salts and solvates thereof. The compounds are useful as antiallergic agents and exhibit excellent bioavailability. 1 wherein R 1 represents hydrogen, OH, alkyl or phenyl alkyl, R 2 , R 3 , R 4 , and R 5 represent hydrogen, halogen, optionally protected hydroxyl, formyl, optionally substituted alkyl, alkenyl, alkoxy or the like, and Q represents a group selected from the following groups (i) to (iv), halogen, or alkoxy: 2

  本发明提供了以前药的三环三唑苯并戊二烯衍生物。根据本发明的化合物是由公式（I）表示的，并且是药理学上可接受的盐和溶剂化物。这些化合物可用作抗过敏剂，并表现出优异的生物利用度。其中R1代表氢，OH，烷基或苯基烷基，R2、R3、R4和R5代表氢，卤素，可选保护的羟基，甲酰基，可选取代的烷基，烯基，烷氧基或类似物，而Q代表从以下组（i）到（iv）中选择的一组，卤素或烷氧基。
• TRICYCLIC TRIAZOLOBENZAZEPINE DERIVATIVES, PROCESS FOR PRODUCING THE SAME, AND ANTIALLERGIC
  申请人：Meiji Seika Kaisha, Ltd.

  公开号：EP1026167A1

  公开（公告）日：2000-08-09

  Tricyclic triazolobenzazepine derivatives in the form of a prodrug are provided. The compounds according to the present invention are those represented by formula (I) and pharmacologically acceptable salts and solvates thereof. The compounds are useful as antiallergic agents and exhibit excellent bioavailability. wherein R1 represents hydrogen, OH, alkyl or phenyl alkyl, R2, R3, R4, and R5 represent hydrogen, halogen, optionally protected hydroxyl, formyl, optionally substituted alkyl, alkenyl, alkoxy or the like, and Q represents a group selected from the following groups (i) to (iv), halogen, or alkoxy:

  本发明提供了原药形式的三环三唑并氮杂卓衍生物。根据本发明的化合物是由式（I）代表的化合物及其药理学上可接受的盐和溶液。这些化合物可用作抗过敏剂，并具有良好的生物利用度。 其中 R1 代表氢、OH、烷基或苯基烷基、 R2、R3、R4 和 R5 代表氢、卤素、任选保护的羟基、甲酰基、任选取代的烷基、烯基、烷氧基或类似物，以及 Q 代表选自以下基团 (i) 至 (iv)、卤素或烷氧基：