2,2-dimethyl-3-(morpholin-4-ylmethyl)penta-3,4-dienal | 862591-75-1

• 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: 2,2-dimethyl-3-(morpholin-4-ylmethyl)penta-3,4-dienal
• 英文别名: 2,2-dimethyl-3-(morpholinomethyl)penta-3,4-dienal
• CAS: 862591-75-1
• 化学式: C₁₂H₁₉NO₂
• 分子量: 209.288
• InChiKey: UGXGYGSBIVGBIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,2-dimethyl-3-(morpholin-4-ylmethyl)penta-3,4-dienal 在 盐酸羟胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以80%的产率得到2,2-dimethyl-3-(morpholinomethyl)penta-3,4-dienal oxime
  参考文献：
  名称：

  Allenyloxime—a new source of heterocyclizations to stable cyclic nitrones

  摘要：

  A variety of conditions including reductive and/or basic reagents in aqueous or alcoholic solution was applied to 2,2-dimethylpenta-3,4-dienal oxime. Formation of various five-membered heterocycles with excellent chemical selectivity was observed. Most of the reactions yielded cyclic nitrones with stable dipolar structure and unique functionalities present. All products of cyclization were isolated and fully characterized. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.07.113
• 作为产物：
  描述：

  4-{4-[(2-methylprop-1-en-1-yl)oxy]but-2-yn-1-yl}morpholine 以78%的产率得到2,2-dimethyl-3-(morpholin-4-ylmethyl)penta-3,4-dienal
  参考文献：
  名称：

  通过热引发分子内交叉环加成 3-取代的高烯基醛连氮的稠合四环杂环

  摘要：

  研究了热引发的 3-取代对称高烯基吖嗪 (5) 的分子内交叉环加成反应。它们的环化导致了有趣的新稠合杂环系统，该系统由四个五元环和两个氮杂原子组成 (6)。吖嗪的制备基于高烯基醛 (4) 与肼反应的应用。高烯醛 (4) 通过新的 N,N-二取代 4-[(2-methylprop-1-en-1-yl)oxy]but-2-yn)-1-胺 (3a-f) 的克莱森重排制备由 2-methylprop-1-en-1-yl prop-2-yn-1-yl 醚 (2) 通过曼尼希反应制备。该反应的成功基于改进的 1-氯-2-甲基丙基丙-2-炔-1-基醚 (1) 合成的无溶剂程序及其转化为完全可分离的 2-甲基丙-1-烯-1-基高产率的丙-2-炔-1-基醚(2)。

  DOI：

  10.1002/ejoc.200400814

文献信息

• Substituted homoallenyl aldehydes and their derivatives. Part 2: Azines
  作者：Juraj Galeta、Stanislav Man、Aneta Valoušková、Milan Potáček

  DOI：10.2478/s11696-012-0238-z

  日期：2013.1.1

  This paper deals with the preparation of a variously substituted non-symmetrical azine set. The starting molecule for their preparation was a protected hydrazone. The protection was performed applying Zwierzak’s method. This procedure is based on the transfer of hydrazine to diethylhydrazidophosphate, which reacts with aldehydes to produce protected hydrazones. In the second step of the procedure, under the action of sodium hydride, the addition of another aldehyde affords non-symmetrical azines in the reaction with the protected hydrazine. The procedure was shown to be a useful and effective method. In this, the second part of our study, we present results devoted to the preparation and full identification of non-symmetrical azines.

  摘要：本文介绍了一种制备多取代非对称吖啶衍生物的方法。制备这些化合物的起始分子是受保护的酰肼。保护是采用Zwierzak方法进行的。该过程基于将肼转移给二乙基肼磷酸酯，后者与醛反应产生受保护的酰肼。在该过程的第二步中，在氢氧化钠的作用下，通过与受保护的酰肼反应，另一个醛的加成得到了非对称吖啶衍生物。该过程被证明是一种有用和有效的方法。在我们的研究的第二部分中，我们介绍了关于制备和完全鉴定非对称吖啶衍生物的结果。
• Fused Tetracyclic Heterocycles by Thermally Initiated Intramolecular Criss-Cross Cycloaddition of 3-Substituted Homoallenylaldazines
  作者：Hana Zachová、Stanislav Man、Marek Nečas、Milan Potáček

  DOI：10.1002/ejoc.200400814

  日期：2005.6

  A thermally initiated intramolecular criss-cross cycloaddition of 3-substituted symmetrical homoallenyl azines (5) was searched. Their cyclization led to interesting new fused heterocyclic systems consisting of four five-membered rings with two nitrogen heteroatoms (6). The preparation of azines was based on application of homoallenylaldehydes (4) in reaction with hydrazine. The homoallenylaldehydes

  研究了热引发的 3-取代对称高烯基吖嗪 (5) 的分子内交叉环加成反应。它们的环化导致了有趣的新稠合杂环系统，该系统由四个五元环和两个氮杂原子组成 (6)。吖嗪的制备基于高烯基醛 (4) 与肼反应的应用。高烯醛 (4) 通过新的 N,N-二取代 4-[(2-methylprop-1-en-1-yl)oxy]but-2-yn)-1-胺 (3a-f) 的克莱森重排制备由 2-methylprop-1-en-1-yl prop-2-yn-1-yl 醚 (2) 通过曼尼希反应制备。该反应的成功基于改进的 1-氯-2-甲基丙基丙-2-炔-1-基醚 (1) 合成的无溶剂程序及其转化为完全可分离的 2-甲基丙-1-烯-1-基高产率的丙-2-炔-1-基醚(2)。
• Allenyloxime—a new source of heterocyclizations to stable cyclic nitrones
  作者：Marian Buchlovič、Stanislav Man、Milan Potáček

  DOI：10.1016/j.tet.2008.07.113

  日期：2008.10

  A variety of conditions including reductive and/or basic reagents in aqueous or alcoholic solution was applied to 2,2-dimethylpenta-3,4-dienal oxime. Formation of various five-membered heterocycles with excellent chemical selectivity was observed. Most of the reactions yielded cyclic nitrones with stable dipolar structure and unique functionalities present. All products of cyclization were isolated and fully characterized. (C) 2008 Elsevier Ltd. All rights reserved.