dimethyl 2-(methylthio)fumarate | 76706-91-7

• 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: dimethyl 2-(methylthio)fumarate
• 英文别名: dimethyl (Z)-2-methylsulfanylbut-2-enedioate
• CAS: 76706-91-7
• 化学式: C₇H₁₀O₄S
• 分子量: 190.22
• InChiKey: XYTLVUMBYITHKO-PLNGDYQASA-N

物化性质

• 沸点：
  275.6±30.0 °C(Predicted)
• 密度：
  1.200±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 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：
  77.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dimethyl 2-(methylthio)fumarate 在 18-冠醚-6 、 二苯基甲烷 、 potassium hydride 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 23.17h， 生成 1-Azabicyclo[3.2.0]heptane-2,3-dicarboxylic acid,6-[1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]-3-(methylthio)-7-oxo-,disodium salt
  参考文献：
  名称：

  从青霉素到青霉素和碳青霉烯。V通过（3 + 2）环化合成卡宾布南骨架

  摘要：

  碳青霉烯衍生物是通过新型的（3 + 2）环化2） 4-碘甲基-2-氮杂环丁烷酮（1和6）和2-硫取代的富马酸二甲酯衍生物（2，R = CH 3，C 6 H 5）制备的。

  DOI：

  10.1016/s0040-4039(01)91547-3
• 作为产物：
  描述：

  3-benzoyl-1,2-dicarbomethoxy-3,5-dihydro-5-(methylthio)indolizine 生成 dimethyl 2-(methylthio)fumarate 、 3-benzoyl-1,2-dicarbomethoxy-3,5-dihydro-5-hydroxyindolizine
  参考文献：
  名称：

  Cycloaddition reactions of pyridinium and related azomethine ylides

  摘要：

  The Rh(H)-catalyzed reaction of alpha-diazoacetophenone in the presence of 2-(methylthio)pyridine and dimethyl acetylenedicarboxylate gave 3-benzoyl-1,2-dicarbomethoxy-3,5-dihydro-5-(methylthio)-indolizine. The formation of the cycloadduct proceeds via a pyridinium ylide formed by attack of the nitrogen lone pair on the electrophilic keto carbenoid. A related cyclization occurred using 1-diazo-3-[(2-pyridyl)thio]-2-propanone. The Rh(II)-catalyzed reaction of 1-(3'-diazoacetonyl)-2-pyridone with DMAD was also found to give cycloadducts derived from an azomethine ylide. The initial reaction involves generation of the expected carbonyl ylide dipole by intramolecular cyclization of the keto carbenoid onto the oxygen atom of the amide group. A subsequent proton exchange generates the thermodynamically more stable azomethine ylide which is trapped by DMAD. Azomethine ylide cycloadducts derived from keto carbenoid cyclization onto a thiobenzoxazole are also formed. When 1-diazo-3-[(2-benzoxazolyl)thio]-2-propanone was used, the initially formed cycloadduct underwent a subsequent 1,3-sigmatropic thio shift. An analogous cyclization occurred using 2-(4-diazo-3-oxobutyl)benzoxazole. In addition to undergoing dipolar cycloaddition, the highly stabilized dipole formed from this benzoxazole loses a proton to produce a cyclic ketene N,O-acetal. This compound reacts further with DMAD to eventually produce a novel phenolic lactam whose structure was established by an X-ray crystal structure analysis.

  DOI：

  10.1021/jo00057a029

文献信息

• From Penicillin to Penem and Carbapenem. IX. C₁-Unit Introduction and the Carbapenam Synthesis from the Penicillin Molecule
  作者：Katsumi Fujimoto、Yuji Iwano、Koichi Hirai

  DOI：10.1246/bcsj.59.1887

  日期：1986.6

  An effective method for (R)-1-hydroxyethylation of benzyl bis(phenylseleno)penicillanate is described. The hydroxyethylated product was transformed into the 4-methylsulfonyl- and 4-phenylsulfonyl-2-azetidinone derivatives. These monocyclic compounds were reacted with potassium cyanide under two-phase conditions to give the 4-cyano-2-azetidinone derivative (C1-unit introduction) in high yield. The cyano group was then converted into the iodomethyl group. Using the 4-iodomethyl-2-azetidinone derivative an isopenam derivative was synthesized. Furthermore, carbapenam derivative were also constructed by a novel [3+2] cyclization reaction between 4-iodomethyl-2-azetidinone and dimethyl 2-methylthio- and 2-phenylthiofumarate.

  本研究描述了一种有效的方法，用于(R)-1-羟乙基化双(苯基硒)青霉烷酸苄酯。羟乙基化产物转化为 4-甲磺酰基和 4-苯磺酰基-2-氮杂环丁酮衍生物。在两相条件下，这些单环化合物与氰化钾反应，得到高产率的 4-氰基-2-氮杂环丁酮衍生物（C1-单位引入）。氰基随后转化为碘甲基。利用 4-碘甲基-2-氮杂环丁酮衍生物合成了异培南衍生物。此外，通过 4-iodomethyl-2-azetidinone 与 2-甲硫基和 2-苯硫基富马酸二甲酯之间的新型 [3+2] 环化反应，还合成了碳青霉烯类衍生物。
• Feit, Ben-Ami; Haag, Brigitte; Kast, Juergen, Journal of the Chemical Society. Perkin transactions I, 1986, p. 2027 - 2036
  作者：Feit, Ben-Ami、Haag, Brigitte、Kast, Juergen、Schmidt, Richard R.

  DOI：——

  日期：——
• VEDEJS, E.;WEST, F., J. ORG. CHEM., 1983, 48, N 24, 4773-4774
  作者：VEDEJS, E.、WEST, F.

  DOI：——

  日期：——