3-methyl-3-phenylcarbamoyl-acrylic acid | 80818-08-2

• 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: 3-methyl-3-phenylcarbamoyl-acrylic acid
• 英文别名: Citraconsaeure-mono-anilid；(Z)-4-anilino-3-methyl-4-oxobut-2-enoic acid
• CAS: 80818-08-2
• 化学式: C₁₁H₁₁NO₃
• 分子量: 205.213
• InChiKey: VAJPJRSEWCFQPT-FPLPWBNLSA-N

物化性质

• 沸点：
  443.3±37.0 °C(Predicted)
• 密度：
  1.281±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-methyl-3-phenylcarbamoyl-acrylic acid 以 氘代二甲亚砜 为溶剂， 生成 (Z)-2-Methyl-4-oxo-4-phenylaminobut-2-enoic acid
  参考文献：
  名称：

  胺对柠康酸酐的作用。（Z）-2-甲基-3-吡咯烷基羰基丙烯酸的X射线晶体结构

  摘要：

  柠康酸与15种伯胺和仲胺的反应得到了异丁烯二酸（2）和（3）的混合物，其中前者占主导地位。变暖时，更丰富的异构体重排为热力学稳定的N-取代的（Z）-2-甲基-3-氨基甲酰基丙烯酸（3）。通过X射线分析确认了吡咯烷化物（3q）的结构。描述了将吡咯烷化物转化为4-甲基-6-吡咯烷酮-1，3-恶嗪-2-酮（7）的失败尝试。

  DOI：

  10.1039/p19810002890
• 作为产物：
  描述：

  (Z)-(2-methyl-4-(4-nitrophenylamino)-4-oxo)but-2-enoic acid 以 四氢呋喃 为溶剂， 反应 26.0h， 生成 3-methyl-3-phenylcarbamoyl-acrylic acid
  参考文献：
  名称：

  Substituent effects on the regioselectivity of maleamic acid formation and hydrogen chloride addition to N-aryl maleimides

  摘要：

  伊托酸酐与芳胺反应生成一种取代基控制的区域异构体平衡混合物，包括(Z)-2-甲基-和(Z)-3-甲基-4-氧代-4-(芳胺基)丁-2-烯酸。电子供给基团有利于对C-5羰基的亲核攻击，而电子吸引基团的存在则增强了对C-2羰基攻击的偏好。将(Z)-2-甲基-和(Z)-3-甲基-4-氧代-4-(芳胺基)丁-2-烯酸与SOCl₂-Et₃N在THF中处理，得到相应的马来咪唑，产率较高；而在相同条件下，马来酸酐与芳胺的加成产物主要生成相应的3-氯-1-芳基吡咯烷-2,5-二酮和马来咪唑，比例依赖于取代基。

  DOI：

  10.3906/kim-1203-34

文献信息

• Succinimide and maleimide derivatives and their use as topoisomerase II catalytic inhibitors
  申请人：Topo Target ApS

  公开号：US20030032625A1

  公开（公告）日：2003-02-13

  Maleimide and succinimide derivatives were found to be effective topoisomerase II catalytic inhibitors. Due to this property, the maleimide and succinimide derivatives were investigated for their use as cytostatic agents and thus in the treatment of cancer. The compounds of the invention can be used in combination treatments with other cytostatic agents, such as topoisomerase II poisons. The maleimide and succinimide derivatives, due to their effective topoisomerase II catalytic inhibitory activity, are also useful as extravasation agents, such as upon administration of a topoisomerase II poison.

  Maleimide和succinimide衍生物被发现是有效的拓扑异构酶II催化抑制剂。由于这种特性，对maleimide和succinimide衍生物进行了研究，以评估它们作为细胞静止剂并在癌症治疗中的应用。该发明的化合物可与其他细胞静止剂（如拓扑异构酶II毒素）联合治疗。由于其有效的拓扑异构酶II催化抑制活性，maleimide和succinimide衍生物还可用作逸出剂，例如在给予拓扑异构酶II毒素后。
• SUCCINIMIDE AND MALEIMIDE DERIVATIVES AND THEIR USE AS TOPOISOMERASE II CATALYTIC INHIBITORS
  申请人：Jensen Buhl Peter

  公开号：US20070196360A1

  公开（公告）日：2007-08-23

  Maleimide and succinimide derivatives were found to be effective topoisomerase II catalytic inhibitors. Due to this property, the maleimide and succinimide derivatives were investigated for their use as cytostatic agents and thus in the treatment of cancer. The compounds of the invention can be used in combination treatments with other cytostatic agents, such as topoisomerase II poisons. The maleimide and succinimide derivatives, due to their effective topoisomerase II catalytic inhibitory activity, are also useful as extravasation agents, such as upon administration of a topoisomerase II poison.

  Maleimide和succinimide衍生物被发现是有效的拓扑异构酶II催化抑制剂。由于这种特性，研究了maleimide和succinimide衍生物作为细胞静止剂的用途，因此用于癌症的治疗。该发明的化合物可以与其他细胞静止剂，如拓扑异构酶II毒素，组合使用。由于其有效的拓扑异构酶II催化抑制活性，maleimide和succinimide衍生物也可用作外渗剂，例如在给予拓扑异构酶II毒素时。
• Maleamic and Citraconamic Acids, Methyl Esters, and Imides
  作者：NARIMAN B. MEHTA、ARTHUR P. PHILLIPS、(MRS.) FLORENCE FU LUI、RONALD E. BROOKS

  DOI：10.1021/jo01076a038

  日期：1960.6
• [EN] SUCCINIMIDE AND MALEIMIDE DERIVATIVES AND THEIR USE AS TOPOISOMERASE II CATALYTIC INHIBITORS<br/>[FR] DERIVES DE SUCCINIMIDE ET DE MALEIMIDE ET LEUR UTILISATION COMME INHIBITEURS CATALYTIQUES DE LA TOPOISOMERASE II
  申请人：TOPO TARGET APS

  公开号：WO2002078679A2

  公开（公告）日：2002-10-10

  Maleimide and succinimide derivatives were found to be effective topoisomerase II catalytic inhibitors. Due to this property, the maleimide and succinimide derivatives were investigated for their use as cytostatic agents and thus in the treatment of cancer. The compounds of the invention can be used in combination treatments with other cytostatic agents, such as topoisomerase II poisons. The maleimide and succinimide derivatives, due to their effective topoisomerase II catalytic inhibitory activity, are also useful as extravasation agents, such as upon administration of a topoisomerase II poison. Formula (I), wherein -J- is selected from the group consisting of (A) and (B). A compound of formula (II) for use as medicament. A compound of formula (III).
• Substituent effects on the regioselectivity of maleamic acid formation and hydrogen chloride addition to N-aryl maleimides
  作者：YELİZ FATURACI、NECDET COŞKUN

  DOI：10.3906/kim-1203-34

  日期：——

  Itaconic anhydride reacts with aryl amines to give a substituent controlled equilibrium mixture of regioisomeric (Z)-2-methyl- and (Z)-3-methyl-4-oxo-4-(arylamino)but-2-enoic acids. Electron-donating groups favor nucleophilic attack on C-5 carbonyl, while the presence of electron-withdrawing groups enhances the bias for attack on C-2 carbonyl. The treatment of (Z)-2-methyl- and (Z)-3-methyl-4-oxo-4-(arylamino)but-2-enoic acids with SOCl_2-Et_3N in THF provided the corresponding maleimides in high yields while under the same conditions the maleic anhydride aryl amine addition products gave predominately the corresponding 3-chloro-1-arylpyrrolidine-2,5-diones and maleimides in substituent dependent ratio.

  伊托酸酐与芳胺反应生成一种取代基控制的区域异构体平衡混合物，包括(Z)-2-甲基-和(Z)-3-甲基-4-氧代-4-(芳胺基)丁-2-烯酸。电子供给基团有利于对C-5羰基的亲核攻击，而电子吸引基团的存在则增强了对C-2羰基攻击的偏好。将(Z)-2-甲基-和(Z)-3-甲基-4-氧代-4-(芳胺基)丁-2-烯酸与SOCl₂-Et₃N在THF中处理，得到相应的马来咪唑，产率较高；而在相同条件下，马来酸酐与芳胺的加成产物主要生成相应的3-氯-1-芳基吡咯烷-2,5-二酮和马来咪唑，比例依赖于取代基。