1'-[(N-benzylcarbamoyl)methyl]-1',3'-dihydro-3',3'-dimethyl-6-nitrospiro[1-benzopyran-2,2'-indole]

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1'-[(N-benzylcarbamoyl)methyl]-1',3'-dihydro-3',3'-dimethyl-6-nitrospiro[1-benzopyran-2,2'-indole]
• 英文别名: N-benzyl-2-(3',3'-dimethyl-6-nitrospiro[chromene-2,2'-indol]-1'(3'H)-yl)acetamide；N-benzyl-2-(3',3'-dimethyl-6-nitrospiro[chromene-2,2'-indole]-1'-yl)acetamide
• 化学式: C₂₇H₂₅N₃O₄
• 分子量: 455.513
• InChiKey: ASNIQXCCTHMPIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  87.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1'-[(N-benzylcarbamoyl)methyl]-1',3'-dihydro-3',3'-dimethyl-6-nitrospiro[1-benzopyran-2,2'-indole] 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 以38%的产率得到(5aSR,12RS,13RS)-12,13-dihydro-5a,13-methano-6,6-dimethyl-2-nitro-6H-1,3-benzoxazepino[3,2-a]indole-12-(N-benzylcarboxamide)
  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：

  1-benzyl-1,2,3,9a-tetrahydro-9,9,9a-trimethyl-9H-imidazo[1,2-a]indol-2-one 、 5-硝基水杨醛 以 溶剂黄146 为溶剂， 以39%的产率得到1'-[(N-benzylcarbamoyl)methyl]-1',3'-dihydro-3',3'-dimethyl-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

文献信息

• 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.