(Z,Z,Z,Z)-1,2,5,6,9,10,13,14-octathiacyclohexadeca-3,7,11,15-tetraene

• 分子结构分类: 有机化合物 - 有机硫化合物 - 有机二硫化物
• 英文名称: (Z,Z,Z,Z)-1,2,5,6,9,10,13,14-octathiacyclohexadeca-3,7,11,15-tetraene
• 英文别名: (3Z,7Z,11Z,15Z)-1,2,5,6,9,10,13,14-octathiacyclohexadeca-3,7,11,15-tetraene
• 化学式: C₈H₈S₈
• 分子量: 360.68
• InChiKey: ZOQNXVFZKNWMJV-JCJVRDIZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  202
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  1,2,5,6-tetrathiocin 以 氯仿 、 乙腈 为溶剂， 反应 4.5h， 以76%的产率得到(Z,Z,Z,Z)-1,2,5,6,9,10,13,14-octathiacyclohexadeca-3,7,11,15-tetraene
  参考文献：
  名称：

  Synthesis, Structure, and Ring Conversion of 1,2-Dithiete and Related Compounds

  摘要：

  3,4-Bis(methoxycarbonyl)-1,2-dithiete (6), 3,4,7,8-tetrakis(methoxycarbonyl)-1,2,5,6-tetrathiocin (8), and (Z,ZZ,Z)-3,4,7,8, 11,12,15,16-octakis(methoxycarbonyl)-1,2,5,6,9, 10, 13,14-octathiacyclohexadeca-3,7,11,15-tetraene (9) were synthesized by oxidation of titanocene dithiolene complex 4 with sulfuryl chloride, and the crystal structures of 6 and 8 were characterized by X-ray crystallographic analysis which revealed planar and twist geometries, respectively. Tetrathiocin 1, 11, and 12, and 16-membered cyclic compound 3 were also obtained by oxidation of the corresponding dithiolate or dithiolene complex. Dithiete 6 underwent tetramerization selectively to give 16-membered cyclic product 9 even at room temperature. Ring conversion reactions also proceeded among the 4-, 8-, and 16-membered unsaturated cyclic compounds possessing disulfide bonds under various conditions, such as in polar solvent or in the presence of silica gel. The ring-size selectivity of these ring conversion reactions was studied using ab initio molecular orbital calculations.

  DOI：

  10.1021/jo9806714

文献信息

• Synthesis and Reactions of 1,2-Dithiete and Related Compounds
  作者：Toshio Shimizu、Hideyuki Murakami、Yukako Kobayashi、Kazuko Iwata、Nobumasa Kamigata

  DOI：10.1080/10426509908546506

  日期：1999.1

  obtained by oxidation of titanocene dithiolene complex with sulfuryl chloride, and the crystal structures of 1 and 2 were determined by X-ray crystallographic analysis. Novel ring conversion reaction among the compounds was found under various conditions, such as in non-polar solvent, in polar solvent, and in the presence of silica-gel.

  双(甲氧基羰基)-1,2-二硫醚1、环状二聚体2和四聚体3是由二茂钛二硫烯配合物与磺酰氯氧化得到的，1和2的晶体结构由X射线晶体分析确定。在各种条件下，如在非极性溶剂、极性溶剂和硅胶存在下，发现了化合物之间新的环转化反应。
• Shimizu, Toshio; Iwata, Kazuko; Kamigata, Nobumasa, Angewandte Chemie, 1996, vol. 108, # 20, p. 2505 - 2507
  作者：Shimizu, Toshio、Iwata, Kazuko、Kamigata, Nobumasa

  DOI：——

  日期：——
• Shimizu, Toshio; Iwata, Kazuko; Murakami, Hideyuki, Phosphorus, Sulfur and Silicon and the Related Elements, 1997, vol. 120, p. 457 - 458
  作者：Shimizu, Toshio、Iwata, Kazuko、Murakami, Hideyuki、Kamigata, Nobumasa

  DOI：——

  日期：——
• Shimizu, Toshio; Iwata, Kazuko; Kamigata, Nobumasa, Angewandte Chemie, <hi>1996</hi>, vol. 108, # 20, p. 2505 - 2507
  作者：Shimizu, Toshio、Iwata, Kazuko、Kamigata, Nobumasa

  DOI：——

  日期：——
• Shimizu, Toshio; Iwata, Kazuko; Murakami, Hideyuki, Phosphorus, Sulfur and Silicon and the Related Elements, <hi>1997</hi>, vol. 120, p. 457 - 458
  作者：Shimizu, Toshio、Iwata, Kazuko、Murakami, Hideyuki、Kamigata, Nobumasa

  DOI：——

  日期：——