N-phenyl-maleamic acid methyl ester | 80167-50-6

• 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: N-phenyl-maleamic acid methyl ester
• 英文别名: N-Phenyl-maleamidsaeure-methylester；Methyl-maleanilat；Methyl maleanilate；methyl (Z)-4-anilino-4-oxobut-2-enoate
• CAS: 80167-50-6
• 化学式: C₁₁H₁₁NO₃
• 分子量: 205.213
• InChiKey: YKDPLKWAVZDAJU-FPLPWBNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-phenyl-maleamic acid methyl ester 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 反应 10.0h， 以90%的产率得到methyl (E)-4-oxo-4-(phenylamino)but-2-enoate
  参考文献：
  名称：

  N-Bromosuccinimide-dibenzoyl peroxide/azabisisobutyronitrile: a reagent for Z- to E-alkene isomerization

  摘要：

  N-Bromosuccinimide-dibenzoyl peroxide/azobisisobutyronitrile is used to carry out several types of Z- to E-alkene isomerizations. The NBS-bromination conditions are sufficient for both allylic bromination and alkene isomerization. When the allylic hydrogens are not available in substrates, only the isomerization of the alkene takes place. The present conditions for isomerization of carbon-carbon double bonds are mild and efficient. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)01054-8
• 作为产物：
  描述：

  苯胺 在 potassium carbonate 、 对甲苯磺酸 作用下， 以 neat (no solvent, solid phase) 为溶剂， 反应 0.17h， 生成 N-phenyl-maleamic acid methyl ester
  参考文献：
  名称：

  Kumar, Padam Praveen; Rama Devi; Dubey, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2013, vol. 52, # 8, p. 1166 - 1171

  摘要：

  DOI：

文献信息

• Derivatives of aryl amines containing the cytotoxic 1,4-dioxo-2-butenyl pharmacophore
  作者：Amitabh Jha、Chandrani Mukherjee、Ashok K. Prasad、Virinder S. Parmar、Manjula Vadaparti、Umashankar Das、Erik De Clercq、Jan Balzarini、James P. Stables、Anuraag Shrivastav、Rajendra K. Sharma、Jonathan R. Dimmock

  DOI：10.1016/j.bmcl.2010.01.098

  日期：2010.3

  Several series of compounds containing the 1,4-dioxo-2-butenyl moiety have been prepared as candidate cytotoxins, including the methyl N-arylmaleamates, methyl N-arylfumaramates, and N-arylmaleimides. In addition, the N-arylisomaleimides were synthesized which are the structural isomers of N-arylmaleimides. These compounds were evaluated against human Molt 4/C8 and CEM T-lymphocytes as well as murine

  已制备了若干系列含有 1,4-二氧-2-丁烯基部分的化合物作为候选细胞毒素，包括N-芳基马来酸甲酯、N-芳基富马酸甲酯和N-芳基马来酰亚胺。此外，合成了N-芳基异马来酰亚胺，它是N-芳基马来酰亚胺的结构异构体。这些化合物针对人 Molt 4/C8 和 CEM T 淋巴细胞以及鼠 L1210 细胞进行了评估。N-芳基富马酸甲酯显示出最高的细胞毒性效力，尤其是甲基N-(3,4-二氯苯基)富马酸盐对 L1210 细胞的作用是马法兰的六倍，在 Molt 4/C8 试验中与该药物等效。通过使用模型苄基硫醇对代表性化合物进行硫醇化来证明所研究化合物的亲电性。甲基ñ - （3,4-二氯苯基）fumaramate和甲基ñ - （4-氯苯基）马来酰胺酸抑制人Ñ -myristoyltransferase，可能的分子靶标，在高微摩尔范围。QSAR 和分子建模揭示了许多分子的不同结构特征与细胞毒性效力之间的一些
• Process for producing unsaturated dicarboxylic acid imide compound
  申请人：MATSUSHITA ELECTRIC WORKS, LTD.

  公开号：EP0387381A1

  公开（公告）日：1990-09-19

  A process for producing an unsaturated di­carboxylic acid imide compound of formula (I): wherein D represents a divalent organic group having at least one carbon/carbon double bond; R¹ represents an n-­valent organic group having at least one carbon atom; and n is an integer of 1 or above, which comprises reacting an unsaturated amide acid compound of formula (II): wherein D, R¹, and n are as defined above, with an orthoester of formula (III): R²-C⁅OR³]₃      (III) wherein R² and R³, which may be the same or different, each represents a monovalent organic group having at least one carbon atom, to form an unsaturated dicarboxylic acid amide acid ester compound of formula (IV): wherein D, R¹, R³, and n are as defined above, and then imidating the compound of formula (IV).

  一种制备式（I）的不饱和二羧酸酰亚胺化合物的方法：其中D表示至少具有一个碳/碳双键的二价有机基团；R¹表示至少具有一个碳原子的n价有机基团；n为1或以上的整数；包括将式（II）的不饱和酰胺酸化合物与式（III）的正酯发生反应：R²-C⁅OR³]₃      （III），其中R²和R³，可以相同也可以不同，每个都表示至少具有一个碳原子的一价有机基团，形成式（IV）的不饱和二羧酸酰胺酸酯化合物：其中D，R¹，R³和n如上定义，然后对式（IV）的化合物进行亚胺化。
• Kumar, Padam Praveen; Reddy, Y. Dathu; Kumari, Y. Bharathi, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2014, vol. 53, # 4, p. 392 - 398
  作者：Kumar, Padam Praveen、Reddy, Y. Dathu、Kumari, Y. Bharathi、Devi, B. Rama、Dubey

  DOI：——

  日期：——
• Gupta; Wagh, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2006, vol. 45, # 3, p. 697 - 702
  作者：Gupta、Wagh

  DOI：——

  日期：——
• Easwar, Srinivasan; Argade, Narshinha P., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2002, vol. 41, # 9, p. 1899 - 1901
  作者：Easwar, Srinivasan、Argade, Narshinha P.

  DOI：——

  日期：——