(E)-N-[2-(4-Methoxyphenyl)ethenyl]morpholine | 72680-71-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (E)-N-[2-(4-Methoxyphenyl)ethenyl]morpholine
• 英文别名: (E)-1-(p-methoxyphenyl)-2-morpholino-ethene；4-(4-methoxy-styryl)-morpholine；4-[(E)-2-(4-methoxyphenyl)ethenyl]morpholine
• CAS: 72680-71-8
• 化学式: C₁₃H₁₇NO₂
• 分子量: 219.283
• InChiKey: SVHPZXXVQXCXIN-VOTSOKGWSA-N

物化性质

• 熔点：
  84-86 °C(Solv: methanol (67-56-1); water (7732-18-5))
• 沸点：
  373.6±42.0 °C(Predicted)
• 密度：
  1.149±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-N-[2-(4-Methoxyphenyl)ethenyl]morpholine 生成 4-[2-bromo-2-(4-methoxyphenyl)ethylidene]morpholin-4-ium;bromide
  参考文献：
  名称：

  CRISPI, G.;GIACCONI, P.;ROSSI, E.;STRADI, R., SYNTHESIS, BRD, 1982, N 9, 787-788

  摘要：

  DOI：
• 作为产物：
  描述：

  4-[(二苯基磷酰)甲基]吗啉 在 potassium hydride 作用下， 生成 (E)-N-[2-(4-Methoxyphenyl)ethenyl]morpholine
  参考文献：
  名称：

  通过霍纳-维蒂希反应进行烯胺合成

  摘要：

  芳族和脂族醛可通过与-吗啉代甲基二苯基膦氧化物（）的Horner-Wittig反应转化为它们的同源烯胺。

  DOI：

  10.1016/s0040-4039(01)86312-7

文献信息

• Substituted coumarin amidines: useful building blocks for the preparation of [1]benzopyrano[4,3-b]pyridin-5-one and [1]benzopyrano[4,3-d]pyrimidin-5-one derivatives
  作者：Egle M. Beccalli、Alessandro Contini、Pasqualina Trimarco

  DOI：10.1016/j.tet.2005.03.050

  日期：2005.5

  synthesis of [1]benzopyrano[4,3-b]pyridin-5-ones 4a–f and 4g–j starting from 3-formylcoumarin and 3-cyanocoumarin N-functionalized amidines 3a–f and 3g–j, respectively, was reported. The ring-closure reaction mechanism, under basic or acidic media, was proposed. Furthermore, the reaction of 3-formylamidines 3a,c–f with ammonium acetate gave good yields of 2-substituted [1]benzopyrano[4,3-d]pyrimidin-5-ones

  的[1]苯并吡喃并[4,3-合成b ]吡啶-5-酮4A - ˚F和4克- Ĵ从3- formylcoumarin和3-氰基香豆素起始ñ -官能化脒3A - ˚F和3克- Ĵ，分别是报告。提出了在碱性或酸性介质下的闭环反应机理。此外，3-甲酰idine3a，c - f与乙酸铵的反应产生了2-取代的[1]苯并吡喃并[4,3 - d ]嘧啶-5-酮7的良好收率。
• New synthetic approach to [1]benzopyrano[4,3-b]pyridin-5-one derivatives
  作者：Egle M. Beccalli、Alessandro Contini、Pasqualina Trimarco

  DOI：10.1016/j.tetlet.2004.03.009

  日期：2004.4

  A new synthesis of [1]benzopyrano[4,3-b]pyridin-5-ones 4 was developed starting from 3-formyl-coumarin N-functionalized amidines 3. The reaction is based likely on the intramolecular cyclocondensation of the C-α amidinic carbanion in basic medium on the formyl group.

  从3-甲酰基香豆素N-官能化am 3开始，开发了[1]苯并吡喃并[4,3 - b ]吡啶-5-酮4的新合成方法。该反应很可能是基于在甲酰基的碱性介质中C-α氨基碳负离子的分子内环缩合。
• ν-Triazolines. Part 42. Study on the reactivity of 4,5-dihydro-1-(6-methyl-2-oxo-2H-pyran-4-yl)-5-morpholino-ν-triazoles. Synthetic approach to pyrano[4,3-b]pyrrol-4(1H)-ones
  作者：Emanuela Erba、Donato Pocar、Pasqualina Trimarco

  DOI：10.1039/b008531f

  日期：——

  Pyrolysis of 4-aryl-5-morpholino-4,5-dihydrotriazoles 3 affords two products: pyrano[4,3-b]pyrrol-4(1H)-ones 4 and arylacetamidines 5. The reaction mechanism of this transformation is discussed and reaction conditions optimized to enhance the formation of pyrrole-fused pyran-2-one derivatives 4. 2-Aminoaziridines are considered to be key intermediates in this transformation.

  4-芳基-5-吗啉代-4,5-二氢三唑 3 的热解得到两种产物：吡喃并[4,3-b]吡咯-4(1H)-酮 4 和芳基乙脒 5。讨论了该转化的反应机理并优化反应条件以增强吡咯稠合吡喃-2-酮衍生物4的形成。2-氨基氮丙啶被认为是该转化中的关键中间体。
• Inverse electron demand hetero-Diels–Alder reaction in preparing 1,4-benzodioxin from o-quinone and enamine
  作者：Jinsong Zhang、Chris Taylor、Erich Bowman、Leo Savage-Low、Michael W. Lodewyk、Larry Hanne、Guang Wu

  DOI：10.1016/j.tetlet.2013.09.013

  日期：2013.11

  A process for synthesizing 1,4-benzodioxin, through oxidation of a phenol to an o-quinone followed by treatment with an enamine, has been developed. Adduct stereochemistry is found to be retained via this one-pot reaction. The method uses hypervalent iodine reagent under mild conditions and is compatible with a wide scope of phenols and enamines. Published by Elsevier Ltd.
• The First Rhodium-Catalyzed Anti-Markovnikov Hydroamination: Studies on Hydroamination and Oxidative Amination of Aromatic Olefins
  作者：M. Beller、H. Trauthwein、M. Eichberger、C. Breindl、J. Herwig、T. E. Müller、O. R. Thiel

  DOI：10.1002/(sici)1521-3765(19990401)5:4<1306::aid-chem1306>3.0.co;2-4

  日期：1999.4.1

  The first transition-metal-catalyzed regiospecific anti-Markovnikov hydroamination of aromatic olefins is reported. Styrene and substituted styrenes react with secondary aliphatic amines, especially morpholine and N-arylpiperazines, in the presence of cationic rhodium complexes to give 2-aminoethenylbenzene and 2-aminoethylbenzene derivatives. Cationic [Rh(cod)(2)]+BF4- and various phosphines (1:2-mixture) were employed as in situ catalysts. According to labeling experiments, there is no evidence that the hydroamination is a consecutive hydrogenation of a previously formed enamine. Hydroamination with simple secondary amines, for example piperidine, can also be achieved by the use of a higher olefin concentration and higher reaction temperatures than those given in previously published reaction procedures. Kinetic investigations of the major reaction pathway reveal that the reaction rate of the oxidative amination and the hydroamination is dependent on the styrene and on the catalyst concentration, and independent of the amine concentration. Experiments that employed deuterium-labeled amines (N-D) provided evidence that the mechanism involves an amine-activating pathway, The substituents on the styrene, the phosphine ligand, and the solvent influence the yield of the aminations and the enamine:alkylamine ratio.