(Z)-4-(2,6-dimethylphenylamino)-4-oxobut-2-enoic acid | 31460-31-8

• 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: (Z)-4-(2,6-dimethylphenylamino)-4-oxobut-2-enoic acid
• 英文别名: (2,6-dimethylphenyl)maleamic acid；N-(2,6-dimethylphenyl)-maleamic acid；Maleinsaeure-mono-<2.6-dimethyl-anilid>；Maleinsaeure-mono-2,6-dimethyl-anilid；(Z)-4-(2,6-dimethylanilino)-4-oxobut-2-enoic acid
• CAS: 31460-31-8
• 化学式: C₁₂H₁₃NO₃
• 分子量: 219.24
• InChiKey: BDIUUKLMBSBKIT-SREVYHEPSA-N

物化性质

• 熔点：
  186 °C
• 沸点：
  436.3±45.0 °C(Predicted)
• 密度：
  1.243±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  (Z)-4-(2,6-dimethylphenylamino)-4-oxobut-2-enoic acid 在 四丁基氢氧化铵 作用下， 以 甲醇 、 水 为溶剂， 生成 N-(2,6-dimethylphenyl)-maleamic acid tetrabutylammonium salt
  参考文献：
  名称：

  N-Phenyl-maleic acid amides for regulating the growth and development of

  摘要：

  本发明揭示了一种方法和组合物，用于调节植物的生长和发育，特别是用于瘦果和幼果，促进和促进果实脱离，并加速和调节果实成熟，通过使用公式##STR1##的N-苯基-马来酸酰胺或其盐，其中R.sub.1和R.sub.2彼此独立地为氢，卤素或具有1-4个碳原子的烷基。

  公开号：

  US04125398A1
• 作为产物：
  描述：

  马来酸酐 、 2,6-二甲基苯胺 以 氯仿 为溶剂， 生成 (Z)-4-(2,6-dimethylphenylamino)-4-oxobut-2-enoic acid
  参考文献：
  名称：

  含有细胞毒性 1,4-dioxo-2-butenyl 药效团的芳胺衍生物

  摘要：

  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

  DOI：

  10.1016/j.bmcl.2010.01.098

文献信息

• Palladium-Catalyzed Silane/Siloxane Reductions in the One-Pot Conversion of Nitro Compounds into Their Amines, Hydroxylamines, Amides, Sulfon­amides, and Carbamates
  作者：Robert Maleczka、Ronald Rahaim

  DOI：10.1055/s-2006-950231

  日期：——

  A combination of palladium(II) acetate, aqueous potassi- um fluoride, and polymethylhydrosiloxane (PMHS) facilitates the room-temperature reduction of aromatic nitro compounds to anilines. These reactions tend to be quick (30 min), high-yielding, and tolerate a range of other functional groups. Replacement of PMHS/KF with triethylsilane allows for the reduction of aliphatic nitro compounds to their

  醋酸钯 (II)、氟化钾水溶液和聚甲基氢硅氧烷 (PMHS) 的组合有助于在室温下将芳香族硝基化合物还原为苯胺。这些反应往往快速（30 分钟）、高产，并且可以耐受一系列其他官能团。用三乙基硅烷代替 PMHS/KF 可以将脂肪族硝基化合物还原为相应的羟胺。根据底物的不同，这两种条件都可以将产物胺原位转化为酰胺、磺酰胺和氨基甲酸酯。
• Rapid and Facile Synthesis of Isomaleimides: Dehydration of Maleamic Acids using Methanesulfonyl Chloride
  作者：Mitchell P. Croatt、Khyarul Alam、Elvis C. McFee

  DOI：10.1055/s-0041-1737414

  日期：2022.7

  The dehydration of maleamic acids using methanesulfonyl chloride as a dehydrating agent to selectively and rapidly (<15 min) generate isomaleimides is reported. A variety of maleamic acid derivatives produce the corresponding isomaleimides in good to excellent yields. Adaptation of this protocol under flow synthesis allows for similar efficiency and decreased reaction times (13 seconds residence time)

  报道了使用甲磺酰氯作为脱水剂对马来酸进行脱水，以选择性和快速（<15 分钟）生成异马来酰亚胺。多种马来酸衍生物以良好至优异的产率生产相应的异马来酰亚胺。在流动合成下对该协议的适应允许类似的效率和减少的反应时间（13 秒的停留时间）。还可以在两步、一瓶操作中将马来酸酐转化为所需的异马来酰亚胺。
• Preparation process of N-substituted monochlorosuccinimide
  申请人：MITSUI TOATSU CHEMICALS, Inc.

  公开号：EP0349259A1

  公开（公告）日：1990-01-03

  N-substituted monochlorosuccinimides e.g., N-phenylmonochlorosuccinimide, can be prepared in a high yield by reacting a maleamic acid, e.g., N-phenylmaleamic acid, with phosgene in the presence of a catalyst,e.g., dimethylformamide .

  在催化剂（如二甲基甲酰胺）存在下，马来酰胺酸（如 N-苯基马来酰胺酸）与光气反应，可以高产率制备 N-取代的单氯丁二酰亚胺（如 N-苯基单氯丁二酰亚胺）。
• Syntheses of 4-(3,5-Bisphenylmethylene-4-oxo-piperidin-1-yl)-4-oxo-but-2<b><i>Z</i></b>-enoic Acid Arylamides as Candidate Cytotoxic Agents
  作者：Amitabh Jha、Jonathan R. Dimmock

  DOI：10.1081/scc-120017198

  日期：2003.1.5

  The title compounds were designed and synthesized as candidate cytotoxic agents. They were synthesized by reacting 3,5-bisphenylmethylene-piperidin-4-one with the appropriate 3-arylcarbamoylacrylic acids. These reactions follow an unusual mechanism and deviate from the previously reported reactions on similar substrates.
• Curcumin-inspired cytotoxic 3,5-bis(arylmethylene)-1-(N-(ortho-substituted aryl)maleamoyl)-4-piperidones: A novel group of topoisomerase II alpha inhibitors
  作者：Amitabh Jha、Katherine M. Duffield、Matthew R. Ness、Sujatha Ravoori、Gabrielle Andrews、Khushwant S. Bhullar、H.P. Vasantha Rupasinghe、Jan Balzarini

  DOI：10.1016/j.bmc.2015.08.023

  日期：2015.10

  Three series of novel 3,5-bis(arylmethylene)-1-(N-(ortho-substituted aryl)maleamoyl)-4-piperidones, designed as simplified analogs of curcumin with maleic diamide tether, were synthesized and bioevaluated. These compounds displayed potent cytotoxicity towards human Molt 4/C8 and CEM T-lymphocytes as well as murine L1210 leukemic cells. In contrast, the related N-arylmaleamic acids possessed little or no cytotoxicity in these three screens. Design of these compounds was based on molecular modeling studies performed on a related series of molecule in a previous study. Representative title compounds were found to be significantly potent in inhibiting the activity of topoisomerase II alpha indicating the possible mode of action of these compounds. These compounds were also potent antioxidants in vitro and attenuated the AAPH triggered peroxyl radical production in human fibroblasts. Various members of these series were also well tolerated in both in vitro and in vivo toxicity analysis. (C) 2015 Elsevier Ltd. All rights reserved.