4-amino-5,5-diethyl-5H-1,2-oxathiole-2,2-dioxide | 195370-98-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 4-amino-5,5-diethyl-5H-1,2-oxathiole-2,2-dioxide
• 英文别名: 5,5-Diethyl-2,2-dioxooxathiol-4-amine
• CAS: 195370-98-0
• 化学式: C₇H₁₃NO₃S
• 分子量: 191.251
• InChiKey: DNSFUDCWFDCCQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  77.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-amino-5,5-diethyl-5H-1,2-oxathiole-2,2-dioxide 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以70%的产率得到5,5-diethyl-4-oxo-1,2-oxathiolane-2,2-dioxide
  参考文献：
  名称：

  Synthesis of 4-Amino-5H-1,2-oxathiole 2,2-Dioxides by Cyclization of Cyanohydrin Mesylates. New Routes to β-Amino and β-Keto Sulfonic Acids

  摘要：

  DOI：

  10.1021/jo9707242
• 作为产物：
  描述：

  2-乙基-2-羟基丁腈 在 sodium hydride 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 72.5h， 生成 4-amino-5,5-diethyl-5H-1,2-oxathiole-2,2-dioxide
  参考文献：
  名称：

  Synthesis of 4-Amino-5H-1,2-oxathiole 2,2-Dioxides by Cyclization of Cyanohydrin Mesylates. New Routes to β-Amino and β-Keto Sulfonic Acids

  摘要：

  DOI：

  10.1021/jo9707242

文献信息

• 4-Benzyloxy-γ-Sultone Derivatives: Discovery of a Novel Family of Non-Nucleoside Inhibitors of Human Cytomegalovirus and Varicella Zoster Virus
  作者：Sonia De Castro、Carlos García-Aparicio、Graciela Andrei、Robert Snoeck、Jan Balzarini、María-José Camarasa、Sonsoles Velázquez

  DOI：10.1021/jm8014662

  日期：2009.3.26

  We report the synthesis and antiviral activity of a new family of non-nucleoside antivirals, derived from the 4-keto-1,2-oxathiole-2,2-dioxide (beta-keto-gamma-sultone) heterocyclic system. Several 4- and 5-substituted-5H-1,2-oxathiole-2,2-dioxide derivatives were found to have a selective inhibitory activity against human cytomegalovirus (HCMV) and varicella zoster virus (VZV) replication in vitro, being inactive against a variety of other DNA and RNA viruses. A structure-activity relationship (SAR) study showed that the presence of a benzyl at the 5 position and a benzyloxy substituent at the 4 position are a prerequisite for anti-HCMV and VZV activity. The novel compounds do not show cross-resistance against a wide variety of mutant drug-resistant HCMV strains, pointing to a novel mechanism of antiviral action.
• Synthesis of 4-Amino-5<i>H</i>-1,2-oxathiole 2,2-Dioxides by Cyclization of Cyanohydrin Mesylates. New Routes to β-Amino and β-Keto Sulfonic Acids
  作者：László Poszávácz、Gyula Simig

  DOI：10.1021/jo9707242

  日期：1997.10.1