5-phenyl-2,3,4,5-tetrahydrobenzo[f][1,4]thiazepine | 3358-17-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并硫平类
• 英文名称: 5-phenyl-2,3,4,5-tetrahydrobenzo[f][1,4]thiazepine
• 英文别名: 5-Phenyl-2,3,4,5-tetrahydro-1,4-benzothiazepin；5-Phenyl-2,3,4,5-tetrahydro-1,4-benzothiazepine
• CAS: 3358-17-6
• 化学式: C₁₅H₁₅NS
• 分子量: 241.357
• InChiKey: LSYWVVHWSXDAKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-formyl-5-phenyl-2,3,4,5-tetrahydrobenzo[f][1,4]thiazepine 在 盐酸 、 水 作用下， 以 乙醇 为溶剂， 反应 16.0h， 以80%的产率得到5-phenyl-2,3,4,5-tetrahydrobenzo[f][1,4]thiazepine
  参考文献：
  名称：

  使用改进的 Pictet-Spengler 反应短合成 5-取代-2,3,4,5-四氢苯并[f][1,4]硫氮杂

  摘要：

  5-Substituted-2,3,4,5-tetrahydrobenzo [f][1,4]thiazepines (6) were synthesized using a modified Pictet-Spengler reaction of N-formyliminium ion (4) as the key step. The cyclization of 4 was found to be affected by the acidity of the reaction media, which depended on the structure of the benzene ring. The cyclization of the substrates (4a-g) lacking an electron-donating substituent at the benzene ring proceeded smoothly by using a mixed acid catalyst of trifluoroacetic acid and a small amount of trifluoromethanesulfonic acid, thus giving N-formylbenzothiazepines (5a-g) in good yields. On the other hand, in the case of substrates (4h-j) with the OMe group at the benzene ring, although the cyclization proceeded by use of trifluoroacetic acid as the sole catalyst to give the products (5h-j), the mixed acid catalyst did not induce the cyclization reaction to any extent. The modified Pictet-Spengler reaction, which constitutes imination of 2-(phenylthio)ethanamine (la) with aldehydes (2), and formylation of the resulting imines (3), followed by the acid-catalyzed cyclization of N-formyliminium ion (4), could be carried out as a one-pot procedure, thus providing a convenient methodology for synthesizing various 5-substituted-2,3,4,5-tetrahydrobenzo [f] [1,4] thiazepines (6).

  DOI：

  10.3987/com-17-13705

文献信息

• COMBINATION THERAPY EMPLOYING ILEAL BILE ACID TRANSPORT INHIBITING BENZOTHIEPINES AND HMG Co-A REDUCTASE INHIBITORS
  申请人：G.D. SEARLE & CO.

  公开号：EP0971744A2

  公开（公告）日：2000-01-19
• [EN] COMBINATION THERAPY EMPLOYING ILEAL BILE ACID TRANSPORT INHIBITING BENZOTHIEPINES AND HMG Co-A REDUCTASE INHIBITORS<br/>[FR] TRAITEMENT ASSOCIE UTILISANT DES BENZOTHIEPINES INHIBITRICES DU TRANSPORT ILEAL DE L'ACIDE BILIAIRE ET DES INHIBITEURS DE LA HMG Co-A REDUCTASE
  申请人：——

  公开号：WO1998040375A2

  公开（公告）日：1998-09-17

  [EN] Provided are novel benzothiepines, derivatives, and analogs thereof; pharmaceutical compositions containing them; and methods of using these compounds and compositions in medicine, particularly in the prophylaxis and treatment of hyperlipidemic conditions such as those associated with atherosclerosis or hypercholesterolemia, in mammals. Also provided are compositions and methods for combination therapy employing ileal bile acid transport inhibitors and HMG Co-A reductase inhibitors for the treatment of hyperlipidemic conditions.
  [FR] La présente invention concerne des benzothiépines, certains de leurs dérivés et de leurs analogues. L'invention concerne également des compositions contenant ces benzothiépines, dérivés et analogues. L'invention concerne enfin des procédés permettant d'utiliser ces composés et compositions dans des médicaments, en particulier pour la prophylaxie et le traitement d'états hyperlipidémiques tels que ceux qui sont liés chez les mammifères à l'athérosclérose ou l'hypercholestérolémie. L'invention concerne en outre des compositions et des procédés applicables dans un traitement associé utilisant des benzothiépines inhibitrices du transport iléal de l'acide biliaire et des inhibiteurs de la HMG Co-A réductase pour le traitement d'états hyperlipidémique.