Methyl 1,4,5-trimethyl-1,2,3,4,4a,5,8,8a,octahydropyrido[2,3-b]pyrazine-7-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: Methyl 1,4,5-trimethyl-1,2,3,4,4a,5,8,8a,octahydropyrido[2,3-b]pyrazine-7-carboxylate
• 英文别名: methyl (4aR,8aS)-1,4,5-trimethyl-3,4a,8,8a-tetrahydro-2H-pyrido[2,3-b]pyrazine-7-carboxylate
• 化学式: C₁₂H₂₁N₃O₂
• 分子量: 239.318
• InChiKey: QJDNCLKLLYBSCD-WDEREUQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  36
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  甲基1-甲基-1,4-二氢-3-吡啶羧酸酯 、 N,N'-二甲基乙二胺 在 碘 、 sodium carbonate 作用下， 以 四氢呋喃 为溶剂， 生成 Methyl 1,4,5-trimethyl-1,2,3,4,4a,5,8,8a,octahydropyrido[2,3-b]pyrazine-7-carboxylate
  参考文献：
  名称：

  Vicinal diamination of 1,4-dihydropyridines

  摘要：

  在仲胺存在下，碘与N-烷基-1,4-二氢吡啶1的亲电相互作用可立体选择性生成相应的反式-2,3-二氨基-1,2,3,4-四氢吡啶2，收率令人满意（79-94%）；该方法可用于合成哌啶、吡咯烷、吗啉和哌嗪衍生物。

  DOI：

  10.1039/a807776b

文献信息

• Introduction of Heteroatom-Based Substituents into 1,4-Dihydropyridines by Means of a Halogen-Mediated, Oxidative Protocol: Diamination, Sulfonylation, Sulfinylation, Bis-Sulfanylation, and Halo-Phosphonylation Processes
  作者：Rodolfo Lavilla、Rakesh Kumar、Oscar Coll、Carme Masdeu、Alessandro Spada、Joan Bosch、Enric Espinosa、Elies Molins

  DOI：10.1002/(sici)1521-3765(20000515)6:10<1763::aid-chem1763>3.0.co;2-r

  日期：2000.5.15

  The natural tendency of 1,4-dihydropyridines to undergo "biomimetic" oxidation to afford pyridinium salts can be switched off and, through the use of reagents that interact electrophilically with the enamine moiety present in the heterocyclic system, it is possible to promote alternative oxidations. In this way, efficient regio- and stereocontrolled synthetic methods have been developed that lead to diversely substituted di- and tetrahydropyridines. These include iodoazidation, diamination, bis-sulfonamidation, sulfonylation, sulfinylation, thiocyanation, sulfanylation, bis-sulfanylation, and halo-phosphonylation processes.