8-Fluoro-2,3-dihydro-5H-benzo[B][1,4]thiazepin-4-one | 1239723-17-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并硫氮卓类
• 英文名称: 8-Fluoro-2,3-dihydro-5H-benzo[B][1,4]thiazepin-4-one
• 英文别名: 8-fluoro-3,5-dihydro-2H-1,5-benzothiazepin-4-one
• CAS: 1239723-17-1
• 化学式: C₉H₈FNOS
• 分子量: 197.233
• InChiKey: DCCPCYAGFHFTPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  bis(2-amino-5-fluorophenyl)disulfide 在 ammonium thioglycolate 、 对甲苯磺酸 作用下， 以 邻二甲苯 、 N,N-二甲基甲酰胺 为溶剂， 生成 8-Fluoro-2,3-dihydro-5H-benzo[B][1,4]thiazepin-4-one
  参考文献：
  名称：

  A Simple and Efficient Method for Synthesis of Benzothiazepine Derivatives

  摘要：

  A series of 1,5-benzothiazepines were synthesized using disulfides and alpha,beta-unsaturated carbonyl or nitrite compounds as reaction substrates. After reductive cleavage of the S-S bond of disulfides, the resulting thiols were reacted with alpha,beta-unsaturated carbonyl or nitrite compounds to generated seven-membered heterocyclic compounds. In the presence of ammonium thioglycolate, the Michael reaction occurred between disulfides (1) and 4-methyl-3-penten-2-one to give 2,2,4-trymethyl-3H-1,5-benzothiazepine derivatives in good yields. When ethyl acrylate or acrylonitrile was used as the Michael acceptor, 90-99% of (2-amino-phenylsulfanyl)propionitriles (3) and/or 92-99% of (2-amino-phenylsulfanyl)propionic acid ethyl esters (4) were produced. Subsequently, the 1,5-benzothiazepine compounds 5 and 6 were obtained due to the cyclization reaction.

  DOI：

  10.3987/com-10-12100

文献信息

• A Simple and Efficient Method for Synthesis of Benzothiazepine Derivatives
  作者：Tetsuo Miyakoshi、Saori Itabashi、Rong Lu

  DOI：10.3987/com-10-12100

  日期：——

  A series of 1,5-benzothiazepines were synthesized using disulfides and alpha,beta-unsaturated carbonyl or nitrite compounds as reaction substrates. After reductive cleavage of the S-S bond of disulfides, the resulting thiols were reacted with alpha,beta-unsaturated carbonyl or nitrite compounds to generated seven-membered heterocyclic compounds. In the presence of ammonium thioglycolate, the Michael reaction occurred between disulfides (1) and 4-methyl-3-penten-2-one to give 2,2,4-trymethyl-3H-1,5-benzothiazepine derivatives in good yields. When ethyl acrylate or acrylonitrile was used as the Michael acceptor, 90-99% of (2-amino-phenylsulfanyl)propionitriles (3) and/or 92-99% of (2-amino-phenylsulfanyl)propionic acid ethyl esters (4) were produced. Subsequently, the 1,5-benzothiazepine compounds 5 and 6 were obtained due to the cyclization reaction.