2-methyl-1,2-propanedithiol | 68281-07-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醇
• 英文名称: 2-methyl-1,2-propanedithiol
• 英文别名: 2-methylpropane-1,2-dithiol
• CAS: 68281-07-2
• 化学式: C₄H₁₀S₂
• 分子量: 122.255
• InChiKey: RSJZKUQJWIKWDY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methyl-1,2-propanedithiol 在 sodium hydroxide 、 potassium iodide 、 碘 作用下， 以 水 为溶剂， 反应 0.5h， 以23%的产率得到3,3,7,7-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：

  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

文献信息

• Catalytic Asymmetric Thioacetalization of Aldehydes
  作者：Benjamin List、Ji Kim、Aurélien Tap、Luping Liu

  DOI：10.1055/s-0036-1588083

  日期：——

  A catalytic enantioselective thioacetalization reaction has been developed. Various aldehydes react with unsymmetrical 1,3- or 1,2-dithiols to furnish chiral, enantioenriched thioacetals in excellent enantioselectivities upon treatment with a nitrated imidodiphosphoric acid catalyst. The transformation is assumed to proceed via a thionium ion intermediate.

  已经开发了催化对映选择性硫代缩醛化反应。各种醛与不对称的 1,3- 或 1,2- 二硫醇反应，在用硝化亚氨基二磷酸催化剂处理后，以优异的对映选择性提供手性、对映体富集的硫缩醛。假设转化是通过硫离子中间体进行的。
• 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.