Methyl 5-[3-[(5-methoxycarbonyl-2-sulfanylidene-1,3-dithiol-4-yl)sulfanyl]propylsulfanyl]-2-sulfanylidene-1,3-dithiole-4-carboxylate | 146581-55-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: Methyl 5-[3-[(5-methoxycarbonyl-2-sulfanylidene-1,3-dithiol-4-yl)sulfanyl]propylsulfanyl]-2-sulfanylidene-1,3-dithiole-4-carboxylate
• CAS: 146581-55-7
• 化学式: C₁₃H₁₂O₄S₈
• 分子量: 488.764
• InChiKey: NYMLJUHWVIUQBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  269
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  Methyl 5-[3-[(5-methoxycarbonyl-2-sulfanylidene-1,3-dithiol-4-yl)sulfanyl]propylsulfanyl]-2-sulfanylidene-1,3-dithiole-4-carboxylate 在 mercury(II) diacetate 、 溶剂黄146 作用下， 以 氯仿 为溶剂， 反应 6.0h， 以80%的产率得到4,4'-propane-1,3-diyldithiobis(5-methoxycarbonyl-1,3-dithiol-2-one)
  参考文献：
  名称：

  An Efficient Synthesis of New-Long-Chain Substituted Tetrathiafulvalene Derivatives Involving Two Tetrathiafulvalene Moieties

  摘要：

  通过缩合二硫代二丙烯双（1,3-二硫杂环戊烯-2-三苯基鏻）高氯酸盐和2-乙基硒-4-十七烷基-1,3-二硫杂环戊烯四氟硼酸盐，并在三乙胺存在下，合成了由两个四硫富瓦烯部分通过二硫代二丙烯桥连接的长链取代基衍生物。通过在亚磷酸三乙酯存在下，将相应的1,3-二硫杂环戊烯-2-酮和1,3-二硫杂环戊烯-2-硫酮衍生物偶联，合成了由十六烷基二硫代二丙烯取代基的衍生物。

  DOI：

  10.1055/s-1997-1412
• 作为产物：
  描述：

  methyl 5-mercapto-2-thioxo-1,3-dithiole-4-carboxylate 、 1,3-二溴丙烷 在 sodium methylate 作用下， 生成 Methyl 5-[3-[(5-methoxycarbonyl-2-sulfanylidene-1,3-dithiol-4-yl)sulfanyl]propylsulfanyl]-2-sulfanylidene-1,3-dithiole-4-carboxylate
  参考文献：
  名称：

  Synthesis and properties of new bridged tetrathiafulvalenes

  摘要：

  The condensation reaction of dithiole phosphonium perchlorates 17 and 18a-c with 2-ethylselenodithiolium tetrafluoroborate 16 in the presence of triethylamine was employed for the high-yield synthesis of four new donors 7a-c, 9 of the tetrathiafulvalene series. The carbomethoxy groups of 7a-c were removed by basic hydrolysis followed by decarboxylation to give 8a-c. Electrochemical studies for seven new TTFs were carried out. An unusual effect resulting in an decrease of the first oxidation potential was observed for 7b. Some properties of the starting 4-mercapto-5-carbomethoxy-1,3-dithiole-2-thione (10) are reported.

  DOI：

  10.1021/jo00058a012

文献信息

• An Efficient Synthesis of New-Long-Chain Substituted Tetrathiafulvalene Derivatives Involving Two Tetrathiafulvalene Moieties
  作者：I. Sudmale、A. Puplovskis、A. Edzina、O. Neilands、V. Khodorkovsky

  DOI：10.1055/s-1997-1412

  日期：1997.7

  Derivatives involving two tetrathiafulvalene moieties linked by an alkylenedithio bridge and long-chain substituents were synthesized by the condensation of alkylenedithiobis(1,3-dithiole-2-triphenylphosphonium) perchlorates and 2-ethylseleno-4-heptadecyl-1,3-dithiolium tetrafluoroborate in the presence of triethylamine. The derivative involving a hexadecyclethylenedithio substituent was synthesized by the coupling of the corresponding 1,3-dithiol-2-one and 1,3-dithiole-2-thione derivatives in the presence of triethyl phosphite.

  通过缩合二硫代二丙烯双（1,3-二硫杂环戊烯-2-三苯基鏻）高氯酸盐和2-乙基硒-4-十七烷基-1,3-二硫杂环戊烯四氟硼酸盐，并在三乙胺存在下，合成了由两个四硫富瓦烯部分通过二硫代二丙烯桥连接的长链取代基衍生物。通过在亚磷酸三乙酯存在下，将相应的1,3-二硫杂环戊烯-2-酮和1,3-二硫杂环戊烯-2-硫酮衍生物偶联，合成了由十六烷基二硫代二丙烯取代基的衍生物。
• Synthesis and properties of new bridged tetrathiafulvalenes
  作者：Ineta V. Sudmale、Gregory V. Tormos、Vladimir Yu. Khodorkovsky、Alma S. Edzina、Ojars J. Neilands、Michael P. Cava

  DOI：10.1021/jo00058a012

  日期：1993.3

  The condensation reaction of dithiole phosphonium perchlorates 17 and 18a-c with 2-ethylselenodithiolium tetrafluoroborate 16 in the presence of triethylamine was employed for the high-yield synthesis of four new donors 7a-c, 9 of the tetrathiafulvalene series. The carbomethoxy groups of 7a-c were removed by basic hydrolysis followed by decarboxylation to give 8a-c. Electrochemical studies for seven new TTFs were carried out. An unusual effect resulting in an decrease of the first oxidation potential was observed for 7b. Some properties of the starting 4-mercapto-5-carbomethoxy-1,3-dithiole-2-thione (10) are reported.
• Preparation of two stereoisomers of the macrocyclic electron donor tetramethoxycarbonyl[5.5]-tetrathiafulvalenophane with bridges containing two sulfur atoms
  作者：O. Neiland、V. Khodorkovskii、M. Utinans、I. Sudmale

  DOI：10.1007/bf02252102

  日期：1999.7