4-Amino-2,3-dihydro<1,5>benzothiazepine | 104004-37-7

• 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: 4-Amino-2,3-dihydro<1,5>benzothiazepine
• 英文别名: 4-amino-2,3-dihydro-1,5-benzothiazepine；2,3-dihydro-1,5-benzothiazepin-4-amine；2,3-Dihydro-1,5-benzothiazepin-4-amin
• CAS: 104004-37-7
• 化学式: C₉H₁₀N₂S
• mdl: MFCD02710537
• 分子量: 178.258
• InChiKey: QRDGQTGQFSOTOP-UHFFFAOYSA-N

物化性质

• 熔点：
  118-119 °C
• 沸点：
  350.0±45.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  63.7
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-Amino-2,3-dihydro<1,5>benzothiazepine 在 水 、 碳酸氢钠 作用下， 以 乙醇 为溶剂， 反应 20.0h， 以55%的产率得到2,3-二氢-1,5-苯并硫氮杂卓-4(5H)-酮
  参考文献：
  名称：

  一种新的杂环系统：咪唑并[2,1-d] [1,5]苯并硫氮杂pine。由4-氨基-2,3-二氢-1,5-苯并噻氮平合成

  摘要：

  描述了4-氨基-2,3-二氢-1,5-苯并噻氮平的合成及其向新杂环咪唑并[2,1- d ] [1,5]苯并噻氮平的转化。

  DOI：

  10.1002/jhet.5570220439
• 作为产物：
  描述：

  双(2-氨基苯基)二硫 在 盐酸 、 ammonium thioglycolate 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 4-Amino-2,3-dihydro<1,5>benzothiazepine
  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

• Palagiano; Arenare; De Caprariis, Il Farmaco, 1996, vol. 51, # 7, p. 483 - 491
  作者：Palagiano、Arenare、De Caprariis、Grandolini、Ambrogi、Perioli、Filippelli、Falcone、Rossi

  DOI：——

  日期：——
• 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.
• Studien zur Chemie von O,N- und S,N-haltigen Heterocyclen, 14. Mitt. Tricyclische 1,5-Benzothiazepine aus 2,3-Dihydro-1,5-benzothiazepin-4-amin
  作者：Thomas Erker、Herbert Bartsch

  DOI：10.1007/bf00810933

  日期：1992.11

  Starting from 2,3-dihydro-1,5-benzothiazepin-4-amine (1) tricyclic 1,5-benzothiazepines were obtained. Reaction with ethyl bromopyruvat and ethyl aminoacetate hydrochloride led to the imidazo[2,1-d][1,5]benzothiazepines 3 and 6, respectively. The triazolo derivative 8 was prepared by treatment of 1 with triethyl orthoacetate/ammonia, followed by oxidative cyclization with sodium hypochlorite.
• WALIA, JASJIT, S.;WALIA, AMRIK, S.;LANKIN, D. C.;PETTERSON, R. C.;SINGH, +, J. HETEROCYCL. CHEM., 1985, 22, N 4, 1117-1119
  作者：WALIA, JASJIT, S.、WALIA, AMRIK, S.、LANKIN, D. C.、PETTERSON, R. C.、SINGH, +

  DOI：——

  日期：——
• 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.