(Z,Z)-bis(2-methoxycarbonylvinyl) sulfide | 16135-28-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (Z,Z)-bis(2-methoxycarbonylvinyl) sulfide
• 英文别名: methyl (Z)-3-[(Z)-3-methoxy-3-oxo-1-propenyl]sulfanyl-2-propenoate；cis,cis-dimethyl 3,3'-thiodiacrylate；Dimethyl-cis,cis-thiodiacrylat；cis.cis-Dimethyl-(3.3'-thiodiacrylat)；Di-(cis-β-methoxycarbonylvinyl)-sulfid；methyl (Z)-3-[(Z)-3-methoxy-3-oxoprop-1-enyl]sulfanylprop-2-enoate
• CAS: 16135-28-7
• 化学式: C₈H₁₀O₄S
• 分子量: 202.231
• InChiKey: HVMQICOARZGTLQ-GLIMQPGKSA-N

物化性质

• 沸点：
  279.1±25.0 °C(Predicted)
• 密度：
  1.198±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  77.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (Z,Z)-3,3'-硫代二丙烯酸二乙酯 在 sodium hydroxide 作用下， 生成 (Z,Z)-bis(2-methoxycarbonylvinyl) sulfide
  参考文献：
  名称：

  Cain,E.N.; Warrener,R.N., Australian Journal of Chemistry, 1970, vol. 23, p. 51 - 72

  摘要：

  DOI：

文献信息

• Acetylenic esters. Part III. Reactions of thiocarbonyl compounds with methyl propiolate, methyl methylpropiolate, and methyl phenylpropiolate
  作者：G. Dallas、J. W. Lown、J. C. N. Ma

  DOI：10.1039/j39680002510

  日期：——

  Non-terminal acetylenic esters react with many thiocarbonyl compounds to form heterocycles or 1 : 1 addition products. Propiolic esters in most cases form isomeric mixtures of dimethyl 3,3′-thiodiacrylates (I). The stereochemical course of the thiolic nucleophilic additions may be controlled for preparative purposes by changes in solvent polarity. All three stereoisomers of (I) have been prepared.

  非末端炔属酯与许多硫代羰基化合物反应形成杂环或1：1加成产物。在大多数情况下，丙酸酯形成3,3'-硫代二丙烯酸二甲酯（I）的异构体混合物。为了制备目的，可以通过改变溶剂极性来控制巯基亲核加成的立体化学过程。（I）的所有三种立体异构体均已制备。与顺式-不同，3-（1,1-二甲基-3-苯基-2-异硫脲基）丙烯酸甲酯的反式异构体完全重排为四取代的硫脲。
• Nucleophilic attack of 2-sulfinyl acrylates: A mild and general approach to sulfenic acid anions
  作者：Suneel P. Singh、Jennifer S. O'Donnell、Adrian L. Schwan

  DOI：10.1039/b917217c

  日期：——

  An increasing number of reactions of sulfenic acid anions are being demonstrated in the literature. As such, mild, general and reliable means for the generation of sulfenates are due. In the current paper, an addition/elimination of 2-sulfinyl acrylates using various nucleophiles is demonstrated and evaluated as a protocol for alkane- and arenesulfenate generation. Cyclohexanethiolate, methoxide and

  文献中已证明亚磺酸阴离子的反应越来越多。因此，应采用温和，通用和可靠的方法生成亚磺酸盐。在当前的论文中，使用各种亲核试剂证明了丙烯酸2-亚磺酰基酯的添加/消除作用，并作为生成链烷烃和芳烃磺酸盐的方法进行了评估。环己烷硫醇盐，甲醇盐和正丁基锂在反应中各有优点，硫醇盐是一种温和，选择性和有效的试剂，可从丙烯酸2-亚磺酰基酯中释放出亚硫酸盐。认识到每个亲核试剂的添加/消除的立体特异性，并且提供了对硫醇盐和甲醇盐的特异性的解释。
• An efficient solvent-tuning approach for the rapid synthesis of thiazolidinone derivatives and the selective synthesis of 2-amino-4H-1,3-thiazin-4-one and dimethyl 3,3′-thiodiacrylates
  作者：Garima Choudhary、Rama Krishna Peddinti

  DOI：10.1016/j.tetlet.2014.08.032

  日期：2014.10

  Green synthetic approach has been developed for the rapid generation of thiazolidinone derivatives as crystallized products under catalyst-free conditions in water by polarity adjustment with ethyl lactate as a co-solvent in excellent yields. Additionally, interesting findings on the synthesis of 2-amino-4H-1,3-thiazin-4-one and dimethyl 3,3'-thiodiacrylates have been reported. (C) 2014 Elsevier Ltd. All rights reserved.
• Stereoselective Metal-Free Reaction of Imidazoles with Isothiocyanates Involving Cyanophenylacetylene: A Shortcut to N-(Z-Alkenyl)imidazole-2-carbothioamides
  作者：Boris Trofimov、Ludmila Andriyankova、Lina Nikitina、Kseniya Belyaeva、Anastasiya Mal'kina、Andrei Afonin、Igor Ushakov

  DOI：10.1055/s-0031-1290442

  日期：2012.9

  N-(Z)-(2-Cyano-1-phenylethenyl)imidazole-2-carbothioamides have been synthesized in up to 91% yield by the new reaction between 1-substituted imidazoles and isothiocyanates in the presence of cyanophenylacetylene under catalyst-and solvent-free conditions at room temperature. The reaction proceeds via zwitterion-carbene intermediates which are trapped by isothiocyanates to form the zwitterion with ambident N-S anionic site, which then undergoes stereo- and regioselective migration of the alkenyl moiety.
• Drozd, V. N.; Petrov, M. L.; Popova, O. A., Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, # 6, p. 1082 - 1087
  作者：Drozd, V. N.、Petrov, M. L.、Popova, O. A.、Vyazgin, A. S.

  DOI：——

  日期：——