6-amino-8-(4-methylphenyl)-2-methyl-7-nitro-1,2,3,4-tetrahydroisoquinoline-5-carbonitrile | 1269507-27-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: 6-amino-8-(4-methylphenyl)-2-methyl-7-nitro-1,2,3,4-tetrahydroisoquinoline-5-carbonitrile
• 英文别名: 6-amino-2-methyl-8-(4-methylphenyl)-7-nitro-3,4-dihydro-1H-isoquinoline-5-carbonitrile
• CAS: 1269507-27-8
• 化学式: C₁₈H₁₈N₄O₂
• 分子量: 322.367
• InChiKey: MTYKEHMPGMXXOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  98.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-甲基-4-哌啶酮 、 (E)-2-(4-methylphenyl)-1-nitroethene 、 丙二腈 在 吗啉 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以78%的产率得到6-amino-8-(4-methylphenyl)-2-methyl-7-nitro-1,2,3,4-tetrahydroisoquinoline-5-carbonitrile
  参考文献：
  名称：

  A three-component domino protocol for the facile synthesis of highly functionalized tetrahydroisoquinolines by creation of their benzene ring

  摘要：

  A simple and efficient one-pot synthesis of novel 6-amino-8-aryl-2-methyl/benzyl-7-nitro-1,2,3,4-tetrahydroisoquinoline-5-carbonitriles from the reaction of 1-methyl/benzylpiperidin-4-one with beta-nitrostyrenes and malononitrile in the presence of morpholine is described. This transformation proceeds through the creation of three C=C bonds, leading to a new benzene ring, and presumably occurs via a domino sequence involving Knoevenagel, Michael, Thorpe-Ziegler, and dehydrogenation reactions. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.12.052

文献信息

• A three-component domino protocol for the facile synthesis of highly functionalized tetrahydroisoquinolines by creation of their benzene ring
  作者：Kamaraj Balamurugan、Veerappan Jeyachandran、Subbu Perumal、J. Carlos Menéndez

  DOI：10.1016/j.tet.2010.12.052

  日期：2011.2

  A simple and efficient one-pot synthesis of novel 6-amino-8-aryl-2-methyl/benzyl-7-nitro-1,2,3,4-tetrahydroisoquinoline-5-carbonitriles from the reaction of 1-methyl/benzylpiperidin-4-one with beta-nitrostyrenes and malononitrile in the presence of morpholine is described. This transformation proceeds through the creation of three C=C bonds, leading to a new benzene ring, and presumably occurs via a domino sequence involving Knoevenagel, Michael, Thorpe-Ziegler, and dehydrogenation reactions. (C) 2010 Elsevier Ltd. All rights reserved.