diisopropyl (Z+E)-2,2'-(1,3-dithiethane-2,4-diylidene)-bis<2-(isopropylthio)dithionoacetate> | 233685-27-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: diisopropyl (Z+E)-2,2'-(1,3-dithiethane-2,4-diylidene)-bis<2-(isopropylthio)dithionoacetate>
• CAS: 233685-27-3
• 化学式: C₁₈H₂₈S₈
• 分子量: 500.948
• InChiKey: RBLBRPXSDAUUAS-LAKJNZHXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.25
• 重原子数：
  26.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  diisopropyl (Z+E)-2,2'-(1,3-dithiethane-2,4-diylidene)-bis<2-(isopropylthio)dithionoacetate> 在 三乙胺 、 氯代肟基乙酸乙酯 作用下， 以 四氢呋喃 为溶剂， 以11%的产率得到(S,S)-diisopropyl (Z)-2,2'-(1,3-dithiethane-2,4-diylidene)-bis<2-(isopropylthio)thioacetate>
  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：

  4,5-diisopropylthio-1,2-dithiole-3-thione 在 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以83%的产率得到diisopropyl (Z+E)-2,2'-(1,3-dithiethane-2,4-diylidene)-bis<2-(isopropylthio)dithionoacetate>
  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