3,6-dithiabicyclo<3.1.0.>hexane | 19858-20-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二噻烷
• 英文名称: 3,6-dithiabicyclo<3.1.0.>hexane
• 英文别名: 3,6-Dithiabicyclo[3.1.0]hexane
• CAS: 19858-20-9
• 化学式: C₄H₆S₂
• 分子量: 118.224
• InChiKey: NJARSZHQRQZJER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  6
• 可旋转键数：
  0
• 环数：
  2.0
• 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

• 作为产物：
  描述：

  (2S)-2-[(2S)-环氧乙烷-2-基]环氧乙烷 在 硫脲 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以25%的产率得到3,6-dithiabicyclo<3.1.0.>hexane
  参考文献：
  名称：

  Synthesis of [4,5-Bis(hydroxymethyl)-1,3-dithiolan-2-yl]nucleosides as Potential Inhibitors of HIV¹

  摘要：

  The synthesis of [4,5-bis(hydroxymethyl)-1,3-dithiolan-2-yl]nucleosides is described. (2S,3S)-1,2: 3,4-Diepoxybutane (13) was reacted with potassium thiocyanate to give (2R,3R)-1,2:3,4-diepithiobutane (14). Thiiranering opening with acetate followed by deacetylation gave (2R,3R)-2,3-dithiothreitol (19) which was silylated and treated with trimethyl orthoformate to give the 2-methoxy-1,3-dithiolane 20. Condensation of 20 with silylated thymine, uracil, N-4-benzoylcytosine and 6-chloropurine using a modified Vorbruggen procedure, followed by deprotection, gave the nucleoside analogues. Compounds 26, 28, and 30 were found to be inactive when tested for anti-HIV activity in vitro.

  DOI：

  10.1021/jo952228o

文献信息

• Synthesis of [4,5-Bis(hydroxymethyl)-1,3-dithiolan-2-yl]nucleosides as Potential Inhibitors of HIV¹
  作者：Jonas Brånalt、Ingemar Kvarnström、Björn Classon、Bertil Samuelsson

  DOI：10.1021/jo952228o

  日期：1996.1.1

  The synthesis of [4,5-bis(hydroxymethyl)-1,3-dithiolan-2-yl]nucleosides is described. (2S,3S)-1,2: 3,4-Diepoxybutane (13) was reacted with potassium thiocyanate to give (2R,3R)-1,2:3,4-diepithiobutane (14). Thiiranering opening with acetate followed by deacetylation gave (2R,3R)-2,3-dithiothreitol (19) which was silylated and treated with trimethyl orthoformate to give the 2-methoxy-1,3-dithiolane 20. Condensation of 20 with silylated thymine, uracil, N-4-benzoylcytosine and 6-chloropurine using a modified Vorbruggen procedure, followed by deprotection, gave the nucleoside analogues. Compounds 26, 28, and 30 were found to be inactive when tested for anti-HIV activity in vitro.