4,4-dimethyl-1,2,3-trithiolane

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三硫杂环戊烷
• 英文名称: 4,4-dimethyl-1,2,3-trithiolane
• 英文别名: 4,4-dimethyltrithiolane
• 化学式: C₄H₈S₃
• 分子量: 152.306
• InChiKey: ULEVNDQGMDVFAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  75.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,4-dimethyl-1,2,3-trithiolane 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 3.0h， 以0.7 g的产率得到2-methyl-1,2-propanedithiol
  参考文献：
  名称：

  Identification, Synthesis, and Conformation of Tri- and Tetrathiacycloalkanes from Marine Bacteria

  摘要：

  [GRAPHICS]Seven new cyclic natural polysulfides 1-7 were identified in extracts of two bacterial Cytophaga strains (CFB-phylum) isolated from biofilms from the North Sea. Their structures are based on mono- and dimeric-cyclization products of 2-methylpropane-1,2- dithiol 8, which was also present in the extract in trace amounts. The structures were deduced by analysis of their mass spectra and confirmed by synthesis. The H-1 NMR spectra of some these compounds suggested a high flexibility of the trithiepane and tetrathiocane systems. Therefore, their conformation was further analyzed by DFT calculations and dynamic NMR spectroscopy. While thiepane 4 possesses a twist-chair lowest energy conformation, its isomers 2 and 3 adopt a chairlike conformation, as does the tetrathiocane 5. In contrast, tetrathiocane 6 favors again a twisted chair conformation.

  DOI：

  10.1021/jo070048w
• 作为产物：
  描述：

  2-chloro-1-((2-chloro-2-methylpropyl)disulfanyl)-2-methylpropane 在 sodium hydrogensulfide 作用下， 以 甲醇 为溶剂， 以25%的产率得到3,3,8,8-tetramethyl-1,2,5,6-tetrathiocane
  参考文献：
  名称：

  Identification, Synthesis, and Conformation of Tri- and Tetrathiacycloalkanes from Marine Bacteria

  摘要：

  [GRAPHICS]Seven new cyclic natural polysulfides 1-7 were identified in extracts of two bacterial Cytophaga strains (CFB-phylum) isolated from biofilms from the North Sea. Their structures are based on mono- and dimeric-cyclization products of 2-methylpropane-1,2- dithiol 8, which was also present in the extract in trace amounts. The structures were deduced by analysis of their mass spectra and confirmed by synthesis. The H-1 NMR spectra of some these compounds suggested a high flexibility of the trithiepane and tetrathiocane systems. Therefore, their conformation was further analyzed by DFT calculations and dynamic NMR spectroscopy. While thiepane 4 possesses a twist-chair lowest energy conformation, its isomers 2 and 3 adopt a chairlike conformation, as does the tetrathiocane 5. In contrast, tetrathiocane 6 favors again a twisted chair conformation.

  DOI：

  10.1021/jo070048w

文献信息

• Identification, Synthesis, and Conformation of Tri- and Tetrathiacycloalkanes from Marine Bacteria
  作者：Paul Sobik、Jörg Grunenberg、Katalin Böröczky、Hartmut Laatsch、Irene Wagner-Döbler、Stefan Schulz

  DOI：10.1021/jo070048w

  日期：2007.5.1

  [GRAPHICS]Seven new cyclic natural polysulfides 1-7 were identified in extracts of two bacterial Cytophaga strains (CFB-phylum) isolated from biofilms from the North Sea. Their structures are based on mono- and dimeric-cyclization products of 2-methylpropane-1,2- dithiol 8, which was also present in the extract in trace amounts. The structures were deduced by analysis of their mass spectra and confirmed by synthesis. The H-1 NMR spectra of some these compounds suggested a high flexibility of the trithiepane and tetrathiocane systems. Therefore, their conformation was further analyzed by DFT calculations and dynamic NMR spectroscopy. While thiepane 4 possesses a twist-chair lowest energy conformation, its isomers 2 and 3 adopt a chairlike conformation, as does the tetrathiocane 5. In contrast, tetrathiocane 6 favors again a twisted chair conformation.