(E)-6-mercaptohex-3-en-1-ol | 1578145-12-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醇
• 英文名称: (E)-6-mercaptohex-3-en-1-ol
• 英文别名: (E)-6-sulfanylhex-3-en-1-ol
• CAS: 1578145-12-6
• 化学式: C₆H₁₂OS
• 分子量: 132.227
• InChiKey: KBDZDBWFJTWBBL-OWOJBTEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  8
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  21.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-6-mercaptohex-3-en-1-ol 、 对硝基苯甲醛 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 0.42h， 以100%的产率得到(E)-2-(4-nitrophenyl)-4,5,8,9-tetrahydro-1,3-oxathionine
  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：

  (E)-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85%的产率得到(E)-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