2-(2-Propyl-[1,3]dioxan-5-ylmethylsulfanyl)-benzothiazole | 355423-25-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 2-(2-Propyl-[1,3]dioxan-5-ylmethylsulfanyl)-benzothiazole
• 英文别名: 2-[(2-Propyl-1,3-dioxan-5-yl)methylsulfanyl]-1,3-benzothiazole
• CAS: 355423-25-5
• 化学式: C₁₅H₁₉NO₂S₂
• 分子量: 309.453
• InChiKey: OWGWHAJOKHFLGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  84.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(2-Propyl-[1,3]dioxan-5-ylmethylsulfanyl)-benzothiazole 在 lithium aluminium tetrahydride 、 ammonium molybdate 、 双氧水 、 sodium hydride 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 水 、 甲苯 为溶剂， 反应 87.5h， 生成 (1R,4S)-4,6-Dimethyl-5-[(E)-2-(2-propyl-[1,3]dioxan-5-yl)-vinyl]-2-oxa-bicyclo[2.2.2]oct-5-ene
  参考文献：
  名称：

  Detours en route to a total synthesis of (+)-cassiol

  摘要：

  A synthesis of the antiulcerogenic compound (+)-cassiol 1b has been achieved in 43% yield starting with lactol (S)-2 and sulfone 26. This short and efficient synthesis features the one-pot Julia olefination reaction of the sodium anion of (S)-2 with 26, through the key intermediate (-)-9. This synthesis has been developed as a result of exploratory experiments including different olefination reactions on 2. An attempt to synthesize the intermediate 9 by an intramolecular aldol condensation approach of the open chain precursor 4 is also described. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00082-x
• 作为产物：
  描述：

  (2-Propyl-[1,3]dioxan-5-yl)-methanol 在 氢氧化钾 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 72.0h， 生成 2-(2-Propyl-[1,3]dioxan-5-ylmethylsulfanyl)-benzothiazole
  参考文献：
  名称：

  Detours en route to a total synthesis of (+)-cassiol

  摘要：

  A synthesis of the antiulcerogenic compound (+)-cassiol 1b has been achieved in 43% yield starting with lactol (S)-2 and sulfone 26. This short and efficient synthesis features the one-pot Julia olefination reaction of the sodium anion of (S)-2 with 26, through the key intermediate (-)-9. This synthesis has been developed as a result of exploratory experiments including different olefination reactions on 2. An attempt to synthesize the intermediate 9 by an intramolecular aldol condensation approach of the open chain precursor 4 is also described. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00082-x