2-methyl-1-morpholinocyclopentadiene

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: 2-methyl-1-morpholinocyclopentadiene
• 英文别名: 4-(2-Methylcyclopenta-1,3-dien-1-yl)morpholine；4-(2-methylcyclopenta-1,3-dien-1-yl)morpholine
• 化学式: C₁₀H₁₅NO
• 分子量: 165.235
• InChiKey: NLQGGZKUBZYSNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,2,4,5-四嗪-3,6-二羧酸二甲酯 、 2-methyl-1-morpholinocyclopentadiene 以 乙腈 为溶剂， 以42%的产率得到4b-Methyl-8a-morpholin-4-yl-4a,4b,8a,9-tetrahydro-2H-2,3,6,7-tetraaza-fluorene-1,4,5,8-tetracarboxylic acid tetramethyl ester
  参考文献：
  名称：

  Tandem ‘inverse electron-demand’ Diels-Alder reactions of dienamines with a 1,2,4,5-tetrazine. A new azo-bridged ring system

  摘要：

  Reaction of (EE)-1-morpholino-2-methylpenta-1,3-diene la with dimethyl 1,2,4,5-tetrazine-3,6-di-carboxylate 2 in acetonitrile solution gives dimethyl 2,5-dimethyl-3-morpholino-8,9-diazatricyclo[2.2.2.0(2,6)]oct-8-ene-1,4-dicarboxylate 4a, in high yield (79%) and with high apparent diastereoselectivity; the 1-(4-methylpiperazino) analogue Ib similarly gives compound 4b (66%). Compounds 4a and 4b are the first recorded representatives of this bridged tricyclic ring system. In contrast 2-methyl-1-morpholinocyclopentadiene 5 reacts with 2 mol. equiv. of the tetrazine 2, giving the cyclopentadipyridazine 6. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10699-2

文献信息

• Tandem ‘inverse electron-demand’ Diels-Alder reactions of dienamines with a 1,2,4,5-tetrazine. A new azo-bridged ring system
  作者：András Kotschy、David M. Smith、Attila Cs. Bényei

  DOI：10.1016/s0040-4039(97)10699-2

  日期：1998.2

  Reaction of (EE)-1-morpholino-2-methylpenta-1,3-diene la with dimethyl 1,2,4,5-tetrazine-3,6-di-carboxylate 2 in acetonitrile solution gives dimethyl 2,5-dimethyl-3-morpholino-8,9-diazatricyclo[2.2.2.0(2,6)]oct-8-ene-1,4-dicarboxylate 4a, in high yield (79%) and with high apparent diastereoselectivity; the 1-(4-methylpiperazino) analogue Ib similarly gives compound 4b (66%). Compounds 4a and 4b are the first recorded representatives of this bridged tricyclic ring system. In contrast 2-methyl-1-morpholinocyclopentadiene 5 reacts with 2 mol. equiv. of the tetrazine 2, giving the cyclopentadipyridazine 6. (C) 1998 Elsevier Science Ltd. All rights reserved.