8-chloro-2-methyl-3,5-dihydro-2H-1,5-benzothiazepin-4-one | 110766-90-0

• 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-chloro-2-methyl-3,5-dihydro-2H-1,5-benzothiazepin-4-one
• CAS: 110766-90-0
• 化学式: C₁₀H₁₀ClNOS
• 分子量: 227.714
• InChiKey: HAWVHDBPMSNRGO-UHFFFAOYSA-N

物化性质

• 熔点：
  220-222 °C(Solv: ethanol (64-17-5))
• 沸点：
  389.7±42.0 °C(Predicted)
• 密度：
  1.279±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  8-chloro-2-methyl-3,5-dihydro-2H-1,5-benzothiazepin-4-one 在 乙酸铵 、 氢氧化钾 、 四丁基溴化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 生成 8-Chloro-2,5-dimethyl-4,5-dihydro-6-thia-3,10b-diaza-benzo[e]azulene
  参考文献：
  名称：

  Studies on annulated 1,4-benzothiazines and 1,5-benzothiazepines. IX. Imidazo [2,1-d][1,5] benzothiazepines: synthesis and in vitro benzodiazepine receptor affinity

  摘要：

  The synthesis of three series of 1- and 2-substituted imidazo[2,1-d][1,5]benzothiazepines is accomplished starting from 1,5-benzothiazepin-4-ones. All the synthesized compounds were evaluated for their affinity for the benzodiazepine receptor, testing their ability to displace [H-3]Flunitrazepam from bovine brain membrane protein. A few of the tested compounds showed good affinity, in particular compound 9a (K-i = 43.00 nM). The GABA-ratio of the active compounds suggests an antagonist or partial agonist activity. The data obtained allow us to draw some comments on the structure-activity relationships.

  DOI：

  10.1016/0223-5234(96)88253-5
• 作为产物：
  描述：

  β-丁内酯 、 2-氨基-5-氯噻吩 在 乙酸酐 作用下， 生成 8-chloro-2-methyl-3,5-dihydro-2H-1,5-benzothiazepin-4-one
  参考文献：
  名称：

  A Convenient One-Pot Synthesis of 2,3-Dihydro-1,5-benzothiazepin-4(5H)-ones

  摘要：

  本文介绍了一种改进的 1,5-苯并硫氮杂卓酮衍生物的一步法合成方法。通过在无水吡啶中与ß-丙二醇内酯或ß-丁内酯反应，然后用乙酸酐处理，可方便地将 2-氨基苯硫酚转化为 2,3-二氢-1,5-苯并硫氮杂卓-4(5H)-酮。注意到了一些取代基的影响。

  DOI：

  10.1055/s-1987-28062

文献信息

• Ambrogi; Grandolini; Rossi, Farmaco, Edizione Scientifica, 1987, vol. 42, # 8, p. 575 - 583
  作者：Ambrogi、Grandolini、Rossi、Tiralti

  DOI：——

  日期：——
• AMBROGI V.; GRANDOLINI G., SYNTHESIS,(1987) N 8, 724-726
  作者：AMBROGI V.、 GRANDOLINI G.

  DOI：——

  日期：——
• A Convenient One-Pot Synthesis of 2,3-Dihydro-1,5-benzothiazepin-4(5<i>H</i>)-ones
  作者：Valeria Ambrogi、Giuliano Grandolini

  DOI：10.1055/s-1987-28062

  日期：——

  An improved one-pot synthesis of 1,5-benzothiazepinone derivatives is described. 2-Aminobenzenethiols are conveniently converted into 2,3-dihydro-1,5-benzothiazepin-4(5H)-ones by reaction with ß-propiol-actone or ß-butyrolactone in anhydrous pyridine followed by treatment with acetic anhydride. Some substituent effects are noted.

  本文介绍了一种改进的 1,5-苯并硫氮杂卓酮衍生物的一步法合成方法。通过在无水吡啶中与ß-丙二醇内酯或ß-丁内酯反应，然后用乙酸酐处理，可方便地将 2-氨基苯硫酚转化为 2,3-二氢-1,5-苯并硫氮杂卓-4(5H)-酮。注意到了一些取代基的影响。
• Studies on annulated 1,4-benzothiazines and 1,5-benzothiazepines. IX. Imidazo [2,1-d][1,5] benzothiazepines: synthesis and in vitro benzodiazepine receptor affinity
  作者：V Ambrogi、G Grandolini、L Perioli、L Giusti、A Lucacchini、C Martini

  DOI：10.1016/0223-5234(96)88253-5

  日期：1995.1

  The synthesis of three series of 1- and 2-substituted imidazo[2,1-d][1,5]benzothiazepines is accomplished starting from 1,5-benzothiazepin-4-ones. All the synthesized compounds were evaluated for their affinity for the benzodiazepine receptor, testing their ability to displace [H-3]Flunitrazepam from bovine brain membrane protein. A few of the tested compounds showed good affinity, in particular compound 9a (K-i = 43.00 nM). The GABA-ratio of the active compounds suggests an antagonist or partial agonist activity. The data obtained allow us to draw some comments on the structure-activity relationships.