2-Benzoyl-1-(2-carbomethoxybenzyl)-1-cyan-1,2-dihydroisochinolin | 145103-18-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 2-Benzoyl-1-(2-carbomethoxybenzyl)-1-cyan-1,2-dihydroisochinolin
• 英文别名: 2-[[2-benzoyl-1-cyano-1,2-dihydroisoquinolin-1-yl]methyl]benzoic acid methyl ester
• CAS: 145103-18-0
• 化学式: C₂₆H₂₀N₂O₃
• 分子量: 408.456
• InChiKey: BIXQXMYHOLYLRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.56
• 重原子数：
  31.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  70.4
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-Benzoyl-1-(2-carbomethoxybenzyl)-1-cyan-1,2-dihydroisochinolin 在 氢氧化钾 、 水 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以80%的产率得到8 (H) Dibenzo-8-chinolizinon
  参考文献：
  名称：

  Synthese von Dibenzo[a,g]chinolizinen — Ein neuer Zugang zu Protoberberinen

  摘要：

  A novel synthesis to prepare dibenzo-8-quinolizinones 8 is reported using the intramolecular cyclisation of the benzylated Reissert compounds 6 for the key step. Methylation of 8 by methyllithium gives partial deoxygenated coralynes 10 which in turn can be reduced by NaBH4 yielding the 8-methyltetrahydro-protoberberines 11. The structures are assigned by NMR-spectroscopy.

  DOI：

  10.1007/bf00811549
• 作为产物：
  描述：

  2-溴甲基苯甲酸甲酯 、 2-苯甲酰基-1-氰基-1,2-二氢异喹啉 在 sodium hydroxide 、 十六烷基三甲基溴化铵 作用下， 以 苯 为溶剂， 反应 20.0h， 以77%的产率得到2-Benzoyl-1-(2-carbomethoxybenzyl)-1-cyan-1,2-dihydroisochinolin
  参考文献：
  名称：

  Synthese von Dibenzo[a,g]chinolizinen — Ein neuer Zugang zu Protoberberinen

  摘要：

  A novel synthesis to prepare dibenzo-8-quinolizinones 8 is reported using the intramolecular cyclisation of the benzylated Reissert compounds 6 for the key step. Methylation of 8 by methyllithium gives partial deoxygenated coralynes 10 which in turn can be reduced by NaBH4 yielding the 8-methyltetrahydro-protoberberines 11. The structures are assigned by NMR-spectroscopy.

  DOI：

  10.1007/bf00811549

文献信息

• Protoberberines from Reissert-Compounds VIII [1]. Oxazoloisoquinolines, New and Efficient Educts for the Synthesis of 8-Oxoprotoberberines
  作者：Eberhard Reimann、Fritz Grasberger、Kurt Polborn

  DOI：10.1007/s00706-003-0013-5

  日期：2003.6

   Certain benzylated oxazoloisoquinolinones readily available from Reissert compounds provided an efficient access to 8-oxoprotoberberines in three steps. A series of these new precursors as well as several oxoprotoberberines were prepared and the scope and limitation of this procedure were investigated.

   可从 Reissert 化合物轻松获得的某些苄基恶唑基异喹啉酮可通过 三个步骤有效地获得8-氧代小pro碱。制备了一系列这些新的前体以及几种氧代小ber碱，并研究了该方法的范围和局限性。
• Synthese von Dibenzo[a,g]chinolizinen — Ein neuer Zugang zu Protoberberinen
  作者：Eberhard Reimann、Helmut Benend

  DOI：10.1007/bf00811549

  日期：1992.10

  A novel synthesis to prepare dibenzo-8-quinolizinones 8 is reported using the intramolecular cyclisation of the benzylated Reissert compounds 6 for the key step. Methylation of 8 by methyllithium gives partial deoxygenated coralynes 10 which in turn can be reduced by NaBH4 yielding the 8-methyltetrahydro-protoberberines 11. The structures are assigned by NMR-spectroscopy.