2-methoxy-2-butenedioic acid dimethyl ester | 26579-97-5

• 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: 2-methoxy-2-butenedioic acid dimethyl ester
• 英文别名: dimethyl 2-methoxymaleate；dimethyl 2-methoxy-butendioate；Dimethyl 2-methoxybut-2-enedioate
• CAS: 26579-97-5
• 化学式: C₇H₁₀O₅
• 分子量: 174.153
• InChiKey: ZJAIMWVOOJQLEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  2-methoxy-2-butenedioic acid dimethyl ester 在 盐酸 作用下， 生成 2-氧代琥珀酸二甲酯
  参考文献：
  名称：

  Diels; Meyer, Justus Liebigs Annalen der Chemie, 1934, vol. 513, p. 129,144

  摘要：

  DOI：
• 作为产物：
  描述：

  甲醇 、 全氟丁二烯 在 sodium 作用下， 生成 2-methoxy-2-butenedioic acid dimethyl ester
  参考文献：
  名称：

  Dedek,V.; Kovac,M., Collection of Czechoslovak Chemical Communications, 1979, vol. 44, p. 2660 - 2671

  摘要：

  DOI：

文献信息

• Isolable Gold(I) Complexes Having One Low-Coordinating Ligand as Catalysts for the Selective Hydration of Substituted Alkynes at Room Temperature without Acidic Promoters
  作者：Antonio Leyva、Avelino Corma

  DOI：10.1021/jo802558e

  日期：2009.3.6

  Hydration of a wide range of alkynes to the corresponding ketones has been afforded in high yields at room temperature by using gold(I)−phosphine complexes as catalyst, with no acidic cocatalysts required. Suitable substrates covering alkyl and aryl terminal alkynes, enynes, internal alkynes, and propargylic alcohols, including enantiopure forms, are cleanly transformed to the corresponding ketones

  通过使用金（I）-膦配合物作为催化剂，无需酸性助催化剂，即可在室温下高收率地将各种炔烃水合为相应的酮。覆盖烷基和芳基末端炔烃，烯炔，内部炔烃和炔丙醇的合适底物，包括对映体纯形式，以接近定量的收率干净地转化为相应的酮。保留存在于底物中的酸不稳定基团。催化活性强烈取决于与金（I）中心配位的膦的性质以及抗衡阴离子AuSPhosNTf 2的柔软度显示更好的活动。在动力学研究的基础上，提出了一种可行的炔烃通过缩酮中间体水合的机理。所描述的催化系统应提供基于汞的方法的有效替代方法，并在合成程序中有用。
• A green and rapid approach for the stereoselective vinylation of phenol, thiol and amine derivatives in water
  作者：Yaghoub Sarrafi、Marzieh Sadatshahabi、Kamal Alimohammadi、Mahmood Tajbakhsh

  DOI：10.1039/c1gc15625j

  日期：——

  The stereoselective formation of C–O, C–S and C–N bonds by the reaction of phenols, thiols and amines with activated alkynes is described. The reactions are successfully conducted in water with excellent yields at room temperature. The lack of organic solvent use in the work-up procedure, the short reaction time and the environmentally benign mild reaction conditions are advantages of this method.

  通过酚、硫醇和胺与活化炔烃的反应，实现了C−O、C−S和C−N键的选择性立体形成。这些反应在室温下水相中以优异的产率成功进行。该方法的优势在于后处理过程中无需使用有机溶剂、反应时间短以及温和的环境友好型反应条件。
• A convenient synthesis of alkyl-2-(2-imino-4-oxothiazolidin-5-ylidene)acetate derivatives involving an electrogenerated base of acetonitrile
  作者：Najoua Sbei、Baya Haouas、Monia Chebbi、Youssef Ben Smida、Youssef Arfaoui、Khaled Boujlel、Mohamed Lamine Benkhoud

  DOI：10.1080/17415993.2016.1259416

  日期：2017.3.4

  ABSTRACT We report a simple method for the synthesis of alkyl-2-(2-imino-4-oxothiazolidin-5-ylidene) acetate derivatives 3 in good yields under mild conditions. The electrogenerated cyanomethyl base (EGB), obtained from electroreduction of acetonitrile-0.1 M TBABF4, assists the reaction between thiourea derivatives 1 and dialkyl acetylene dicarboxylate 2. The expected products, 3/4, and the structure

  摘要 我们报告了一种在温和条件下以良好收率合成烷基-2-(2-imino-4-oxothiazolidin-5-ylidene) 乙酸酯衍生物 3 的简单方法。从乙腈-0.1 M TBABF4 的电还原获得的电生成的氰甲基碱 (EGB) 有助于硫脲衍生物 1 和乙炔二羧酸二烷基酯 2 之间的反应。预期的产物 3/4 和从 X 射线衍射获得的结构证实主要产物是五元杂环3。此外，基于从量子计算获得的热力学和动力学数据，提出了解释反应途径的机制。图形概要
• Phyllostictine A: total synthesis, structural verification and determination of substructure responsible for plant growth inhibition
  作者：Martin Riemer、Veselina V. Uzunova、Nastja Riemer、Guy J. Clarkson、Nicole Pereira、Richard Napier、Michael Shipman

  DOI：10.1039/c8cc03349h

  日期：——

  fungal metabolite and its (6S,7R,8S)-stereochemistry. Both synthetic PA and an analogue containing the 5-methylene-1,5-dihydro-2H-pyrrol-2-one nucleus exhibit μM inhibitory activity in root growth assays against Arabidopsis thaliana, indicating that this heterocyclic subunit is key to the herbicidal activity of the natural product.

  首次报道了叶霉碱 A (PA) 的全合成，证实了这种真菌代谢物的结构及其 (6 S ,7 R ,8 S )-立体化学。合成的 PA 和含有 5-methylene-1,5-dihydro-2 H -pyrrol-2-one 核的类似物在针对拟南芥的根生长试验中均表现出 μM 抑制活性，表明该杂环亚基是除草活性的关键的天然产物。
• The crystal structure of [Mo(NCS)(CO)2(η3-C3H5)(NCMe)2]·MeCN and the reactions of {Mo(CO)2(η3-C3H5)+} containing species with symmetric alkynes
  作者：Jonathan W Goodyear、Clive W Hemingway、Ross W Harrington、Matthew R Wiseman、Brian J Brisdon

  DOI：10.1016/s0022-328x(02)01981-2

  日期：2002.12

  In the solid-state [Mo(NCS)(CO)(2)(eta(3) -C3H5)(NCMe)(2)] (.) MeCN (1) contains a pseudo-octahedral arrangement of ligands about molybdenum, with carbonyls and nitriles in the equatorial plane and an N-bonded thiocyanate 3 group trans to the allyl ligand. In refluxing methanol or acetonitrile both 1, and the analogous chloro-complex [MoCl(CO)(2)(eta(3)-C3H5)(NCMe)(2)] (2) catalytically convert PhCdropCPh to a mixture of hexaphenylbenzene and E,E-1,2,3,4-tetraphenylbutadiene. By contrast MeO(2)CCdropCCO(2)Me is not oligomerised. In methanol, complex 2 dimerises 1,4-diphenylbutadiyne to Z,E-1,4,5,8-tetraphenyl-1,7-octa-3,5-diene-1,7-diyne, whereas in the presence of base both the complex and the diyne, react preferentially with the solvent to generate the [Mo-2(CO)(4)(eta(3)- C3H5)(2)(OMe)(3)](-) anion and Z-1,4-diphenyl-3-methoxy-but-3-ene-1-yne, respectively. (C) 2002 Elsevier Science B.V. All rights reserved.