(Z)-methyl 3-chloroformylacrylate | 41502-62-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (Z)-methyl 3-chloroformylacrylate
• 英文别名: (Z)-methyl 4-chloro-4-oxobut-2-enoate；methoxy-4-oxobut-2-enoic acid chloride；methyl 4–chloro–4–oxo–2–(Z)–butenoate；(Z)-3-chlorocarbonyl acrylic acid methyl ester；Maleic monoacid chloride, methyl ester；methyl (Z)-4-chloro-4-oxobut-2-enoate
• CAS: 41502-62-9
• 化学式: C₅H₅ClO₃
• 分子量: 148.546
• InChiKey: JHDQHPJHLHKZDL-IHWYPQMZSA-N

物化性质

• 沸点：
  199.3±23.0 °C(Predicted)
• 密度：
  1.273±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-methyl 3-chloroformylacrylate 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 2-formylphenyl methyl fumarate
  参考文献：
  名称：

  Microwave-assisted solvent-free intramolecular 1,3-dipolar cycloaddition reactions leading to hexahydrochromeno[4,3-b]pyrroles: scope and limitations

  摘要：

  We report the microwave-assisted solvent-free synthesis of hexahydrochromeno[4,3-b]pyrroles. Intramolecular 1,3-dipolar cycloadditions proceed under these conditions within 15-40 min in 16-84% yields. An influence of the microwave irradiation upon various [3+2] cycloaddition reaction intermediates was studied. Additionally, a scope and limitations of these reactions including an influence of the dipolarophile geometry upon the cycloaddition selectivity and steric demands of the dipole upon its reactivity were also disclosed. These observations led us to postulate a preferable transition state of the reaction. Finally, an influence of the microwave irradiation to the isomerization of activated olefins was also described. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.10.074
• 作为产物：
  描述：

  顺丁烯二酸单甲酯 在 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 生成 (Z)-methyl 3-chloroformylacrylate
  参考文献：
  名称：

  分子内无碱催化维蒂希反应：苯并恶庚啶酮的合成

  摘要：

  通过无碱膦催化的Wittig反应开发了一种简单的两步合成苯并庚二酮的方法。使用3-甲基-1-苯基-2-膦-1-氧化物作为前催化剂，使用三甲氧基硅烷作为还原剂。另外，苯甲酸被用作催化剂以促进氧化膦的还原。机理研究表明，香豆素是副产物的形成，这是通过2D NMR实验确定的。报道了对所制备的苯并庚二酮的代谢活性测试的初步结果。

  DOI：

  10.1021/acs.joc.8b02789

文献信息

• Carboxylic Acid Compounds and Use Thereof
  申请人：Inoue Teruhiko

  公开号：US20070197512A1

  公开（公告）日：2007-08-23

  Provision of a superior URAT1 activity inhibitor effective for the treatment and the like of a pathology involving uric acid, such as hyperuricemia, gouty tophus, acute gouty arthritis, chronic gouty arthritis, gouty kidney, urinary lithiasis, renal dysfunction, coronary heart disease, ischemic cardiac diseases and the like. A URAT1 activity inhibitor containing a compound represented by the following formula [1] or a pharmaceutically acceptable salt thereof, or a solvate thereof as an active ingredient: wherein each symbol is as defined in the specification.

  提供一种优越的URAT1活性抑制剂，用于治疗与尿酸有关的病理，如高尿酸血症、痛风石、急性痛风性关节炎、慢性痛风性关节炎、痛风性肾病、尿路结石、肾功能障碍、冠心病、缺血性心脏病等。 一种包含下式[1]所表示的化合物或其药学上可接受的盐，或其溶剂化合物的URAT1活性抑制剂作为活性成分： 其中每个符号如规范中定义。
• Synthesis, DFT and antimicrobial activity assays in vitro for novel cis/trans-but-2-enedioic acid esters
  作者：Yan-Long Ma、Ru-Jin Zhou、Xing-Ye Zeng、Ya-Xiong An、Song-Shan Qiu、Li-Jun Nie

  DOI：10.1016/j.molstruc.2014.01.063

  日期：2014.4

  could be helpful to understand the various antimicrobial activities among these compounds. The antimicrobial activity of compound 6a was evaluated in vitro against Salmonella choleraesuis subsp. choleraesuis, Lactococcus lactis subsp. lactis and Saccharomyces cerevisiae by time–kill, and it was found that compound 6a exhibited significant microbiocidal activity against the three microorganisms.

  摘要 合成了六种新型顺/反-but-2-烯二酸酯，以发现可以杀死食品相关细菌和真菌的新型生物活性分子。通过熔点、LC-MS、1H NMR和13C NMR分析它们的结构。4-(甲氧羰基)苯基富马酸乙酯(6b)也通过单晶X射线衍射表征。通过测量最小抑菌浓度 (MIC) 在体外评估它们的抗菌活性。与单一的富马酸单甲酯和 4-羟基苯甲酸甲酯相比，这些化合物对所有 8 种微生物都具有更强的抗菌活性。在抗菌和抗真菌化合物中，4-(甲氧基羰基)苯基富马酸甲酯(6a)表现出最好的抗菌活性。这些化合物的电子特性是通过密度泛函理论 (DFT) 方法计算的，基组为 6-31G (d, p)。DFT 研究表明分子静电势 (MEP) 图、ELUMO、能隙、电负性和亲电指数有助于了解这些化合物之间的各种抗菌活性。在体外评估了化合物 6a 对猪霍乱沙门氏菌亚种的抗菌活性。猪霍乱，乳酸乳球菌亚种。通过时间杀死乳酸菌和酿酒酵母，发现化合物
• Sequential [3 + 2] and [4 + 2] Cycloadditions for Stereoselective Synthesis of a Novel Polyheterocyclic Scaffold
  作者：Qing Lu、Xin, Huang、Gonghua Song、Chung-Ming Sun、Jerry P. Jasinski、Amanda C. Keeley、Wei Zhang

  DOI：10.1021/co400026s

  日期：2013.7.8

  A strategy of combining [3 + 2] cycloaddition and intramolecular Diels-Alder reaction is developed for the synthesis of a novel polycyclic scaffold with skeletal and substitutional diversities. Intermediates generated from stereoselective [3 + 2] cycloaddition of azomethine ylides and maleimides were derivatized for intramolecular Diels-Alder reaction of furan to form highly condensed heterocyclic

  开发了一种结合[3 + 2]环加成反应和分子内Diels-Alder反应的策略，用于合成具有骨架和取代多样性的新型多环支架。由偶氮甲亚胺和马来酰亚胺的立体选择性[3 + 2]环加成反应生成的中间体被衍生化，用于呋喃的分子内Diels-Alder反应，形成高度缩合的杂环产物，为外消旋的单一非对映异构体。
• New features of the intramolecular Diels Alder route to hydroisoindoles
  作者：John M. Mellor、Alison M. Wagland

  DOI：10.1016/s0040-4039(00)96724-8

  日期：1987.1

  Regio- and stereo- controlled routes to functionalised hydroisoindoles have been developed by reaction of aminodienes with unsaturated anhydrides or acid chlorides and subsequent elaboration of the Diels Alder adducts.

  通过氨基二烯与不饱和酸酐或酰氯的反应以及随后对Diels Alder加合物的精制，已经开发出了区域和立体控制的功能化氢异吲哚途径。
• NOVEL AMIDE DERIVATIVE FOR INHIBITING THE GROWTH OF CANCER CELLS
  申请人：Lee Kwang-Ok

  公开号：US20100179120A1

  公开（公告）日：2010-07-15

  The present invention provides a novel amide derivative and a pharmaceutically acceptable salt thereof which selectively and effectively inhibits the growth of cancer cells induced by the overexpression of an epidermal growth factor receptor and also prevents the development of drug resistance caused by the mutation of EGFR tyrosine kinase, and a pharmaceutical composition comprising same as an active ingredient.

  本发明提供了一种新型酰胺衍生物及其药学上可接受的盐，该酰胺衍生物能够选择性和有效地抑制由表皮生长因子受体过度表达引起的癌细胞生长，并且还能够防止由EGFR酪氨酸激酶突变引起的药物耐受性的发展。本发明还提供了一种包含该酰胺衍生物作为活性成分的药物组合物。