dimethyl (Z)-2-(phenylthio)-2-butenedioate | 59790-38-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: dimethyl (Z)-2-(phenylthio)-2-butenedioate
• 英文别名: (Phenylthio)fumarsaeure-dimethylester；dimethyl 2-(phenylthio)fumarate；dimethyl phenylsulfanylfumarate；dimethyl 2-phenylthiofumarate；Dimethyl phenylthiofumarate；(Z)-phenylthiylmaleic acid dimethyl ester；dimethyl (Z)-2-phenylsulfanylbut-2-enedioate
• CAS: 59790-38-4
• 化学式: C₁₂H₁₂O₄S
• 分子量: 252.291
• InChiKey: PGZIZNVJOBVEDX-NTMALXAHSA-N

物化性质

• 沸点：
  364.1±42.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 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 (Z)-2-(phenylthio)-2-butenedioate 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以81%的产率得到dimethyl 2-(phenylsulfinyl)fumarate
  参考文献：
  名称：

  Preparation of dimethyl 2-phenylthiomaleate dimethyl 2-phenylthiofumarate, and their sulfoxides

  摘要：

  DOI：

  10.1021/jo00155a033
• 作为产物：
  描述：

  马来酸二甲酯 在 三乙胺 N-氯代丁二酰亚胺 、 三乙胺 作用下， 以 四氯化碳 、 苯 为溶剂， 反应 110.0h， 生成 dimethyl (Z)-2-(phenylthio)-2-butenedioate
  参考文献：
  名称：

  Preparation of dimethyl 2-phenylthiomaleate dimethyl 2-phenylthiofumarate, and their sulfoxides

  摘要：

  DOI：

  10.1021/jo00155a033

文献信息

• Sulfonium Ylides by (3+2) Cycloaddition of Arynes with Vinyl Sulfides: Stereoselective Synthesis of Highly Substituted Alkenes
  作者：Yuanming Li、Christian Mück-Lichtenfeld、Armido Studer

  DOI：10.1002/anie.201608144

  日期：2016.11.7

  of in situ generated arynes with vinyl sulfides provides benzannulated sulfonium ylides in a (3+2) cycloaddition. Trapping of the intermediate ylides with electrophiles (proton transfer or a second aryne addition) and subsequent β‐elimination give rise to di‐, tri‐, or tetrasubstituted alkenes with high stereoselectivity. Experimental studies and DFT calculations provide insight into the mechanisms of

  原位生成的芳烃与乙烯基硫化物的反应可在（3 + 2）环加成反应中提供苯甲酰化sulf化烷基化ides。用亲电子试剂（质子转移或第二个芳烃加成）捕集中间亚烷基并随后进行β-消除反应会生成具有高立体选择性的二，三或四取代烯烃。实验研究和DFT计算可洞悉这些级联反应的机理。
• Generation of Nonstabilized Thiazolium and 2-Methylthiazolium Methylides
  作者：Otohiko Tsuge、Shuji Kanemasa、Satoru Kuraoka

  DOI：10.1246/bcsj.58.1570

  日期：1985.5

  Desilylation of 3-(trimethylsilylmethyl)thiazolium triflates including 2-methyl derivatives with CsF generates the corresponding thiazolium methylides which are trapped with acetylenic and olefinic dipolarophiles. This paper presents the first example for the generation of nonstabilized thiazolium methylides including 2-methyl derivatives.

  3-（三甲基甲硅烷基甲基）噻唑鎓三氟甲磺酸盐与 CsF 的脱甲硅烷基化反应产生相应的噻唑鎓甲基化物，这些甲基化物被炔属和烯属偶极亲和体捕获。本文介绍了生成不稳定噻唑鎓甲基化物（包括 2-甲基衍生物）的第一个例子。
• 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。
• Water-promoted regioselective hydrothiolation of alkynes
  作者：Sukalyan Bhadra、Brindaban C. Ranu

  DOI：10.1139/v09-130

  日期：2009.11

  Water promotes hydrothiolation of unactivated alkynes efficiently without any catalyst or additive. The reaction at room temperature furnishes vinyl sulfides with high regioselectivity via anti-Markovnikov addition. The terminal alkynes provide dithiolanes at 80 °C by bis-addition. The reactions are very clean and high yielding.

  在不使用任何催化剂或添加剂的情况下，水能有效地促进未活化炔烃的氢硫化反应。反应在室温下进行，通过反马尔科夫尼科夫加成法生成具有高区域选择性的乙烯基硫化物。末端炔烃在 80 °C 时通过双加成反应生成二硫环戊烷。反应非常干净，产率高。
• 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。