2-chloro-1-((2-chloro-2-methylpropyl)disulfanyl)-2-methylpropane | 16621-43-5

• 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: 2-chloro-1-((2-chloro-2-methylpropyl)disulfanyl)-2-methylpropane
• 英文别名: bis(2-methyl-2-chloropropyl) disulfide；bis-(2-chloro-2-methyl-propyl)-disulfane；Bis-(2-chlor-2-methyl-propyl)-disulfid；Disulfide, bis(2-chloro-2-methylpropyl)；2-chloro-1-[(2-chloro-2-methylpropyl)disulfanyl]-2-methylpropane
• CAS: 16621-43-5
• 化学式: C₈H₁₆Cl₂S₂
• 分子量: 247.253
• InChiKey: LGWXFHMMYPUWPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  50.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  异丁烯 在 二氯化二硫 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以52%的产率得到2-chloro-1-((2-chloro-2-methylpropyl)disulfanyl)-2-methylpropane
  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

• ——
  作者：I. V. Bodrikov、A. A. Sazhin、I. Yu. Shebelova、A. Yu. Subbotin、T. V. Rybalova、Yu. V. Gatilov、V. A. Barkhash

  DOI：10.1023/a:1020933005986

  日期：——

  In reaction of unsaturated compounds with sulfur dichloride in the presence of dimethyl sulfide radically new induced directions are realized: the reagent is involved as dimer or trimer (formation of di- and trisulfides). Alongside this process a conjugate chlorination occurred with participation of external nucleophiles, dimethyl sulfide and acetonitrile, furnishing sulfonium chlorides and N-substituted acetamides respectively. The relative importance of these alternative reactions depends on solvent, alkene structure, and order of reagents addition.
• US4217232A
  申请人：——

  公开号：US4217232A

  公开（公告）日：1980-08-12