2-(1-acetylazetidin-3-yl)thio-1,3-thiazoline | 1181809-06-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: 2-(1-acetylazetidin-3-yl)thio-1,3-thiazoline
• 英文别名: 1-[3-(4,5-Dihydro-1,3-thiazol-2-ylsulfanyl)azetidin-1-yl]ethanone；1-[3-(4,5-dihydro-1,3-thiazol-2-ylsulfanyl)azetidin-1-yl]ethanone
• CAS: 1181809-06-2
• 化学式: C₈H₁₂N₂OS₂
• 分子量: 216.328
• InChiKey: FOCCZIORJUNFDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  83.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(1-acetylazetidin-3-yl)thio-1,3-thiazoline 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 以75%的产率得到1-acetylazetidine-3-thiol
  参考文献：
  名称：

  Reaction of 1-Azabicyclo[1.1.0]butane with Activated Amides

  摘要：

  1-Azabicyclo[1.1.0]butane (ABB, 1) reacted with 3-acyl-1,3-thiazolidine-2-thiones (7,11a-m) in the presence of a catalytic amount of Mg(OTf)(2) to give the corresponding 2-(1-acylazetidin-3-yl)thio-1,3-thiazolines (8,12a-m). It was hypothesized that this reaction is primarily influenced by a steric bulkiness of acyl groups in 3-acyl-1,3-thiazolidine-2-thiones. Resulting compounds (8, 12k) were readily converted to thiols (13,14), and azetidine-3-thiol hydrochloride (15), which is the key intermediate of 1-(1,3-thiazolin-2-yl)azetidine-3-thiol hydrochloride (4) useful for the preparation of a new oral 1 beta-methylcarbapenem antibiotic L-084, was obtained quantitatively by hydrolysis of 14.

  DOI：

  10.3987/com-09-11677
• 作为产物：
  描述：

  1-氮杂双环[1.1.0]丁烷 、 3-乙酰基噻唑烷-2-硫酮 在 magnesium triflate 作用下， 以 四氢呋喃 为溶剂， 以57%的产率得到2-(1-acetylazetidin-3-yl)thio-1,3-thiazoline
  参考文献：
  名称：

  Reaction of 1-Azabicyclo[1.1.0]butane with Activated Amides

  摘要：

  1-Azabicyclo[1.1.0]butane (ABB, 1) reacted with 3-acyl-1,3-thiazolidine-2-thiones (7,11a-m) in the presence of a catalytic amount of Mg(OTf)(2) to give the corresponding 2-(1-acylazetidin-3-yl)thio-1,3-thiazolines (8,12a-m). It was hypothesized that this reaction is primarily influenced by a steric bulkiness of acyl groups in 3-acyl-1,3-thiazolidine-2-thiones. Resulting compounds (8, 12k) were readily converted to thiols (13,14), and azetidine-3-thiol hydrochloride (15), which is the key intermediate of 1-(1,3-thiazolin-2-yl)azetidine-3-thiol hydrochloride (4) useful for the preparation of a new oral 1 beta-methylcarbapenem antibiotic L-084, was obtained quantitatively by hydrolysis of 14.

  DOI：

  10.3987/com-09-11677

文献信息

• Reaction of 1-Azabicyclo[1.1.0]butane with Activated Amides
  作者：Kazuhiko Hayashi、Eiko Kujime、Hajime Katayama、Shigeki Sano、Yoshimitsu Nagao

  DOI：10.3987/com-09-11677

  日期：——

  1-Azabicyclo[1.1.0]butane (ABB, 1) reacted with 3-acyl-1,3-thiazolidine-2-thiones (7,11a-m) in the presence of a catalytic amount of Mg(OTf)(2) to give the corresponding 2-(1-acylazetidin-3-yl)thio-1,3-thiazolines (8,12a-m). It was hypothesized that this reaction is primarily influenced by a steric bulkiness of acyl groups in 3-acyl-1,3-thiazolidine-2-thiones. Resulting compounds (8, 12k) were readily converted to thiols (13,14), and azetidine-3-thiol hydrochloride (15), which is the key intermediate of 1-(1,3-thiazolin-2-yl)azetidine-3-thiol hydrochloride (4) useful for the preparation of a new oral 1 beta-methylcarbapenem antibiotic L-084, was obtained quantitatively by hydrolysis of 14.