(Z)-S-6-hydroxyhex-3-enyl ethanethioate | 1578145-10-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硫代羧酸及其衍生物
• 英文名称: (Z)-S-6-hydroxyhex-3-enyl ethanethioate
• 英文别名: S-[(Z)-6-hydroxyhex-3-enyl] ethanethioate
• CAS: 1578145-10-4
• 化学式: C₈H₁₄O₂S
• 分子量: 174.264
• InChiKey: BLMOTVZPJNRCLR-IHWYPQMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-S-6-hydroxyhex-3-enyl ethanethioate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以82%的产率得到6(Z)-6-mercaptohex-3-en-1-ol
  参考文献：
  名称：

  Tuning the Reactivity of Oxygen/Sulfur by Acidity of the Catalyst in Prins Cyclization: Oxa- versus Thia-Selectivity

  摘要：

  An unprecedented oxa- versus thia-selectivity has been observed in Prins cyclization of 6-mercaptohex-3-en-1-ol with aldehydes. In the presence of a stoichiometric amount of strong Lewis or Bronsted acids, the reaction provides the hexahydro-2H-thieno[3,2-c]pyran skeleton predominantly via oxonium-Prins cyclization. In contrast, a catalytic amount of weak Lewis or Bronsted acids provides the hexahydro-2H-thiopyrano[4,3-b]furan preferentially through thionium-Prins cyclization.

  DOI：

  10.1021/jo402832t
• 作为产物：
  描述：

  <(Z)-6-(Tetrahydro-2H-pyranyloxy)-3-hexen-1-yl>-p-toluolsulfonat 在 Amberlyst-15 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 (Z)-S-6-hydroxyhex-3-enyl ethanethioate
  参考文献：
  名称：

  Tuning the Reactivity of Oxygen/Sulfur by Acidity of the Catalyst in Prins Cyclization: Oxa- versus Thia-Selectivity

  摘要：

  An unprecedented oxa- versus thia-selectivity has been observed in Prins cyclization of 6-mercaptohex-3-en-1-ol with aldehydes. In the presence of a stoichiometric amount of strong Lewis or Bronsted acids, the reaction provides the hexahydro-2H-thieno[3,2-c]pyran skeleton predominantly via oxonium-Prins cyclization. In contrast, a catalytic amount of weak Lewis or Bronsted acids provides the hexahydro-2H-thiopyrano[4,3-b]furan preferentially through thionium-Prins cyclization.

  DOI：

  10.1021/jo402832t