11-(4-Chloro-phenyl)-12-oxa-10-thia-5-aza-dibenzo[a,g]azulene | 286464-95-7

• 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: 11-(4-Chloro-phenyl)-12-oxa-10-thia-5-aza-dibenzo[a,g]azulene
• 英文别名: 6-(4-Chlorophenyl)-[1]benzofuro[2,3-c][1,5]benzothiazepine
• CAS: 286464-95-7
• 化学式: C₂₁H₁₂ClNOS
• 分子量: 361.851
• InChiKey: GVFBCJUINYHDLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  11-(4-Chloro-phenyl)-12-oxa-10-thia-5-aza-dibenzo[a,g]azulene 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以65%的产率得到trans-2-(4''-chlorophenyl)-4-(2'-hydroxyphenyl)-2,3,4,5-tetrahydro-1,5-benzothiazepine
  参考文献：
  名称：

  An Unexpected Synthesis of Novel Oxygen-Bridged 1,5-Benzothiazepine Derivatives and their Reductive Five-Membered-Ring Opening

  摘要：

  A convenient procedure is reported for the preparation of benzofuro-annelated 2-phenyl-1,5-benzothiazepine derivatives by oxidative cyclocondensation of phenolic beta-diketones with o-aminothiophenol in DMSO. The regiochemistry of these compounds is proven by HMBC signals and the existence of a five-bond F-19,C-13-2 coupling. Surprisingly, treatment with LiAlH4 at room temperature led to a double reduction under opening of the five-membered ring. Refluxing such solutions with a higher amount of LiAlH4 gave rise to a further reduced derivative possessing the trans-configuration. All structures (regio- and stereochemistry) were assigned an the basis of NMR spectroscopic data.

  DOI：

  10.1007/s007060050320
• 作为产物：
  描述：

  1-(4-氯苯基)-3-(2-羟基苯基)丙烷-1,3-二酮 、 2-氨基苯硫醇 以 二甲基亚砜 为溶剂， 反应 5.0h， 以73.4%的产率得到11-(4-Chloro-phenyl)-12-oxa-10-thia-5-aza-dibenzo[a,g]azulene
  参考文献：
  名称：

  An Unexpected Synthesis of Novel Oxygen-Bridged 1,5-Benzothiazepine Derivatives and their Reductive Five-Membered-Ring Opening

  摘要：

  A convenient procedure is reported for the preparation of benzofuro-annelated 2-phenyl-1,5-benzothiazepine derivatives by oxidative cyclocondensation of phenolic beta-diketones with o-aminothiophenol in DMSO. The regiochemistry of these compounds is proven by HMBC signals and the existence of a five-bond F-19,C-13-2 coupling. Surprisingly, treatment with LiAlH4 at room temperature led to a double reduction under opening of the five-membered ring. Refluxing such solutions with a higher amount of LiAlH4 gave rise to a further reduced derivative possessing the trans-configuration. All structures (regio- and stereochemistry) were assigned an the basis of NMR spectroscopic data.

  DOI：

  10.1007/s007060050320