9,9,9a-Trimethyl-1-naphthalen-1-ylmethyl-9,9a-dihydro-1H-imidazo[1,2-a]indol-2-one | 117237-27-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 9,9,9a-Trimethyl-1-naphthalen-1-ylmethyl-9,9a-dihydro-1H-imidazo[1,2-a]indol-2-one
• 英文别名: 9,9,9a-trimethyl-1-(naphthalen-1-ylmethyl)-9,9a-dihydro-1H-imidazo[1,2-a]indol-2(3H)-one；3a,4,4-trimethyl-3-(naphthalen-1-ylmethyl)-1H-imidazo[1,2-a]indol-2-one
• CAS: 117237-27-1
• 化学式: C₂₄H₂₄N₂O
• 分子量: 356.467
• InChiKey: BFFIRSYGRILEQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  9,9,9a-Trimethyl-1-naphthalen-1-ylmethyl-9,9a-dihydro-1H-imidazo[1,2-a]indol-2-one 、 5-硝基水杨醛 以 溶剂黄146 为溶剂， 以60%的产率得到1',3'-dihydro-3',3'-dimethyl-1'-[[N-(1-naphthylmethyl)carbamoyl]methyl]-6-nitrospiro[1-benzopyran-2,2'-indole]
  参考文献：
  名称：

  Cyclization of Nitrospirobenzopyrans to Bridged Benzoxazepino[3,2-a]indoles

  摘要：

  Condensation of 1-substituted 1,2,3,9a-tetrahydro-9H-imidazo[1,2-a]indol-2-ones with 5-nitrosalicylaldehyde afforded 1'-[(N-monosubstituted carbamoyl)methyl]indoline nitrospirobenzopyrans. Treatment of the latter with strong base led to the formation of a mixture of cis/trans-5a,13-methano-1,3-benzoxazepino[3,2-a]indoles. Results of semiempirical calculations gave evidence that such a transformation of nitrospirobenzopyrans to bicyclic indole derivatives could proceed via a single transition state, where the negatively charged carbon atom attacks the vinylic double bond of the spiropyran system.

  DOI：

  10.1007/s00706-005-0504-7
• 作为产物：
  描述：

  9,9,9a-Trimethyl-1,2,3,9a-tetrahydro-9H-imidazo<1,2-a>indol-2-one 、 (氯甲基)萘 在 氢氧化钾 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以51%的产率得到9,9,9a-Trimethyl-1-naphthalen-1-ylmethyl-9,9a-dihydro-1H-imidazo[1,2-a]indol-2-one
  参考文献：
  名称：

  Alkylation of 1,2,3,9a-tetrahydro-9H-imidazo[1,2-a]indol-2-ones

  摘要：

  DOI：

  10.1007/bf00475563

文献信息

• SHACHKUS, A. A.;DEGUTIS, YU. A., XIMIYA GETEROTSIKL. SOED.,(1988) N 1, 49-53
  作者：SHACHKUS, A. A.、DEGUTIS, YU. A.

  DOI：——

  日期：——
• Cyclization of Nitrospirobenzopyrans to Bridged Benzoxazepino[3,2-a]indoles
  作者：Neringa Kleizienė、Virginė Amankavičienė、Ulf Berg、Carsten Schicktanz、Klaus Schlothauer、Algirdas Šačkus

  DOI：10.1007/s00706-005-0504-7

  日期：2006.8

  Condensation of 1-substituted 1,2,3,9a-tetrahydro-9H-imidazo[1,2-a]indol-2-ones with 5-nitrosalicylaldehyde afforded 1'-[(N-monosubstituted carbamoyl)methyl]indoline nitrospirobenzopyrans. Treatment of the latter with strong base led to the formation of a mixture of cis/trans-5a,13-methano-1,3-benzoxazepino[3,2-a]indoles. Results of semiempirical calculations gave evidence that such a transformation of nitrospirobenzopyrans to bicyclic indole derivatives could proceed via a single transition state, where the negatively charged carbon atom attacks the vinylic double bond of the spiropyran system.
• Alkylation of 1,2,3,9a-tetrahydro-9H-imidazo[1,2-a]indol-2-ones
  作者：A. A. Shachkus、Yu. A. Degutis

  DOI：10.1007/bf00475563

  日期：1988.1