dimethyl 2-methyl-1-(2-thienyl)-2,3,4,5-tetrahydrocyclopenta[c]azepine-6,8-dicarboxylate | 1175710-67-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: dimethyl 2-methyl-1-(2-thienyl)-2,3,4,5-tetrahydrocyclopenta[c]azepine-6,8-dicarboxylate
• 英文别名: dimethyl 2-methyl-1-thiophen-2-yl-4,5-dihydro-3H-cyclopenta[c]azepine-6,8-dicarboxylate
• CAS: 1175710-67-4
• 化学式: C₁₈H₁₉NO₄S
• 分子量: 345.419
• InChiKey: MWYYXLXIKQAKIM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  56.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  在 N,N'-二环己基碳二亚胺 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以85%的产率得到dimethyl 2-methyl-1-(2-thienyl)-2,3,4,5-tetrahydrocyclopenta[c]azepine-6,8-dicarboxylate
  参考文献：
  名称：

  Formation of [5.5]cyclopentadienidophanes by macrocyclization of [3-(methylammonio)propyl]cyclopentadienides under Mannich conditions

  摘要：

  2-Acyl-1,4-bis(methoxycarbonyl)-3-13-(methylammonio)propyl]cyclopentadienides 1 and aqueous formaldehyde can undergo a double Mannich reaction leading to the bisbetainic 2,12-diazonia[5,5](1,3)cyclopentadienidophanes 2. The success of this macrocyclization reaction seems to depend on the length of the omega-ammonioalkyl chain and the individual acyl substituent. In the cases of omega-(methylammonio)butyl and (omega)-(methylammonio)pentyl chains, as well as with omega-ammoniopropyl derivatives bearing particularly electron-rich 4-methoxybenzoyl or 2-furoyl substituents, a mixture of oligomers is formed. On the other hand, DCC-assisted cyclocondensation of 1b,d (acyl=4-methoxybenzoyl and thiophene-2-carbonyl, respectively) occurs only intramolecularly, leading to the bicyclic 6-aminopentafulvenes 4b,d in good yields. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.05.014