methyl 2-thia-8-oxa-dibenzo[e,h]azulene-1-carboxylate | 1198602-39-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噁庚英
• 英文名称: methyl 2-thia-8-oxa-dibenzo[e,h]azulene-1-carboxylate
• CAS: 1198602-39-9
• 化学式: C₁₈H₁₂O₃S
• 分子量: 308.357
• InChiKey: SDFDINSPAFYNML-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.97
• 重原子数：
  22.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl 2-thia-8-oxa-dibenzo[e,h]azulene-1-carboxylate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 1.0h， 以95%的产率得到(2-thia-8-oxa-dibenzo[e,h]azulen-1-yl)methanol
  参考文献：
  名称：

  2,8-Dithia-dibenzo[e,h]azulenes and Their 8-Oxa Analogs. Synthesis and Anti-inflammatory Activity

  摘要：

  Synthesis of 2,8-dithia-dibenzo[e,h]azulenes (111, X = S) and their 8-oxa analogs (111, X = 0),1 two novel classes of fused heterocyclic compounds, is described. Starting 11H-dibenzo[b,f]thiepin-10-one, 11H-dibenzo[b,f]oxepin-10-one and its 2-chloro derivative (1a-c) were oxidized to 1,2-diketones (2a-c) which subsequently reacted with 2,2'-dimethyl thiodiglycolate to form fused thiophene ring by Hinsberg cyclization reaction. Substituents at positions C(l) and C(3) were then further transformed in order to obtain aminoalkoxy derivatives 8-11. Structures of regioisomers 6c and 6d were elucidated using two-dimensional NMR techniques. All compounds with tetracyclic skeleton were tested in vitro for their anti-inflammatory activity.

  DOI：

  10.3987/com-09-11755
• 作为产物：
  描述：

  monomethyl 2-thia-8-oxa-dibenzo[e,h]azulene-1,3-dicarboxylate 在 铜 作用下， 以62%的产率得到methyl 2-thia-8-oxa-dibenzo[e,h]azulene-1-carboxylate
  参考文献：
  名称：

  2,8-Dithia-dibenzo[e,h]azulenes and Their 8-Oxa Analogs. Synthesis and Anti-inflammatory Activity

  摘要：

  Synthesis of 2,8-dithia-dibenzo[e,h]azulenes (111, X = S) and their 8-oxa analogs (111, X = 0),1 two novel classes of fused heterocyclic compounds, is described. Starting 11H-dibenzo[b,f]thiepin-10-one, 11H-dibenzo[b,f]oxepin-10-one and its 2-chloro derivative (1a-c) were oxidized to 1,2-diketones (2a-c) which subsequently reacted with 2,2'-dimethyl thiodiglycolate to form fused thiophene ring by Hinsberg cyclization reaction. Substituents at positions C(l) and C(3) were then further transformed in order to obtain aminoalkoxy derivatives 8-11. Structures of regioisomers 6c and 6d were elucidated using two-dimensional NMR techniques. All compounds with tetracyclic skeleton were tested in vitro for their anti-inflammatory activity.

  DOI：

  10.3987/com-09-11755