5,5'-dithiobis(4-isopropylthio-1,2-dithiol-3-thione)

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 5,5'-dithiobis(4-isopropylthio-1,2-dithiol-3-thione)
• 英文别名: 4-Propan-2-ylsulfanyl-5-[(4-propan-2-ylsulfanyl-5-sulfanylidenedithiol-3-yl)disulfanyl]dithiole-3-thione
• 化学式: C₁₂H₁₄S₁₀
• 分子量: 478.903
• InChiKey: SNXSVUAHWFYHFI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  267
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  丁炔二酸二甲酯 、 5,5'-dithiobis(4-isopropylthio-1,2-dithiol-3-thione) 以 苯 为溶剂， 反应 0.17h， 以69%的产率得到tetramethyl α,α'-dithiobis(6-isopropylthio-6-thiocarbonyl-1,4-dithiafulvalene-2,3-dicarboxylate)
  参考文献：
  名称：

  Synthesis of Sulfur-Rich 1,2- and 1,3-Dithiolo Disulfides and Thiodesaurines from Diisopropyl Sulfide

  摘要：

  The reaction of diisopropyl sulfide and S2Cl2 in chlorobenzene, in the presence of DABCO, gives 4-isopropylthio-5-isoplopyldithio-1,2-dithiole-3-thion (1) and the dimeric 5,5'-dithiobis(4-isopropylthio-1,2-dithiol-3-thione) (2). If the reaction is performed in the presence of diisopropyl disulfide at the last st-age of the reaction, disulfide 1 is selectively obtained. Some interconversions between 1 and 2 under UV irradiation are described, and a coherent set of reaction pathways far the formation of 1 and 2 are proposed. Treatment of 1 with DMAD in benzene gives the 1:1 adduct 9 in high yield; analogously the bisdithiolo disulfide 2 gives the 1:2 adduct 10, a very sulfur-rich molecule. Treatment of 1 with 1.27 equiv of triphenylphosphine in dicrhloromethane gives 4,5-di(isopropylthio)-1,2-dithiole-3-thione (11), but the treatment of 1 with 2 equiv of Ph3P affords thiodesaurine 12 (Z + E isomers), which was converted into desaurines 14 and 15 by treatment with nitrile oxide 16.

  DOI：

  10.1021/jo9825005
• 作为产物：
  描述：

  2,2'-硫代二丙烷 在 三乙烯二胺 、 二氯化二硫 作用下， 以 氯苯 为溶剂， 以19%的产率得到5,5'-dithiobis(4-isopropylthio-1,2-dithiol-3-thione)
  参考文献：
  名称：

  Synthesis of Sulfur-Rich 1,2- and 1,3-Dithiolo Disulfides and Thiodesaurines from Diisopropyl Sulfide

  摘要：

  The reaction of diisopropyl sulfide and S2Cl2 in chlorobenzene, in the presence of DABCO, gives 4-isopropylthio-5-isoplopyldithio-1,2-dithiole-3-thion (1) and the dimeric 5,5'-dithiobis(4-isopropylthio-1,2-dithiol-3-thione) (2). If the reaction is performed in the presence of diisopropyl disulfide at the last st-age of the reaction, disulfide 1 is selectively obtained. Some interconversions between 1 and 2 under UV irradiation are described, and a coherent set of reaction pathways far the formation of 1 and 2 are proposed. Treatment of 1 with DMAD in benzene gives the 1:1 adduct 9 in high yield; analogously the bisdithiolo disulfide 2 gives the 1:2 adduct 10, a very sulfur-rich molecule. Treatment of 1 with 1.27 equiv of triphenylphosphine in dicrhloromethane gives 4,5-di(isopropylthio)-1,2-dithiole-3-thione (11), but the treatment of 1 with 2 equiv of Ph3P affords thiodesaurine 12 (Z + E isomers), which was converted into desaurines 14 and 15 by treatment with nitrile oxide 16.

  DOI：

  10.1021/jo9825005

文献信息

• Synthesis of Sulfur-Rich 1,2- and 1,3-Dithiolo Disulfides and Thiodesaurines from Diisopropyl Sulfide
  作者：Charles W. Rees、Oleg A. Rakitin、Carlos F. Marcos、Tomás Torroba

  DOI：10.1021/jo9825005

  日期：1999.6.1

  The reaction of diisopropyl sulfide and S2Cl2 in chlorobenzene, in the presence of DABCO, gives 4-isopropylthio-5-isoplopyldithio-1,2-dithiole-3-thion (1) and the dimeric 5,5'-dithiobis(4-isopropylthio-1,2-dithiol-3-thione) (2). If the reaction is performed in the presence of diisopropyl disulfide at the last st-age of the reaction, disulfide 1 is selectively obtained. Some interconversions between 1 and 2 under UV irradiation are described, and a coherent set of reaction pathways far the formation of 1 and 2 are proposed. Treatment of 1 with DMAD in benzene gives the 1:1 adduct 9 in high yield; analogously the bisdithiolo disulfide 2 gives the 1:2 adduct 10, a very sulfur-rich molecule. Treatment of 1 with 1.27 equiv of triphenylphosphine in dicrhloromethane gives 4,5-di(isopropylthio)-1,2-dithiole-3-thione (11), but the treatment of 1 with 2 equiv of Ph3P affords thiodesaurine 12 (Z + E isomers), which was converted into desaurines 14 and 15 by treatment with nitrile oxide 16.