(E)-1-morpholino-3-phenyl-1-propene | 118071-09-3

• 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: (E)-1-morpholino-3-phenyl-1-propene
• 英文别名: 4-[(E)-3-phenylprop-1-enyl]morpholine
• CAS: 118071-09-3
• 化学式: C₁₃H₁₇NO
• 分子量: 203.284
• InChiKey: XALYXNSFYNCQOO-XBXARRHUSA-N

物化性质

• 沸点：
  341.8±41.0 °C(Predicted)
• 密度：
  1.097±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 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：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-1-morpholino-3-phenyl-1-propene 在 甲醇 、 9-borabicyclo[3.3.1]nonane dimer 作用下， 生成 烯丙苯
  参考文献：
  名称：

  Hydroboration. 86. Convenient conversion of aldehydes and ketones into the corresponding alkenes via hydroboration of their enamines. A remarkably simple synthesis of either (Z)- or (E)-alkenes

  摘要：

  Aldehydes and ketones are converted into the corresponding alkenes via hydroboration of their enamines. Hydroboration of aldehyde enamines by 9-borabicyclo[3.3.1]nonane (9-BBN), followed by methanolysis, affords the corresponding terminal alkenes in 75-90% yields. Unsaturated aldehyde enamines produce the corresponding dienes under these conditions. Enamines derived from substituted cyclic ketones and heterocyclic ketones are readily accommodated in this reaction to afford the corresponding alkenes in very good yields. The synthesis of pure (Z)- or (E)-alkenes is readily achieved from the same acyclic ketone enamine by modification of the hydroboration-elimination procedure: (A) hydroboration by 9-BBN followed by methanolysis or (B) hydroboration by borane methyl sulfide (BMS) followed by methanolysis and hydrogen peroxide oxidation. Mechanistic rationale is provided.

  DOI：

  10.1021/jo00004a038
• 作为产物：
  描述：

  4-苯基-1-丁烯 在 4 A molecular sieve 、 臭氧 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 (E)-1-morpholino-3-phenyl-1-propene
  参考文献：
  名称：

  The reactions of the ozonides with secondary amines: An efficient and novel way to prepare tertiary amine from mono- and 1,1-di-substituted alkenes via corresponding ozonides

  摘要：

  DOI：

  10.1016/s0040-4039(00)73982-7

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。
• Synthesis of 4-nitromethylene-1,4-dihydropyrimidine derivatives as pyrimidine nucleoside analogues
  作者：Alessandro Contini、Emanuela Erba、Pasqualina Trimarco

  DOI：10.1016/j.tet.2008.09.079

  日期：2008.12

  4-dihydropyrimidine derivatives as pyrimidine nucleoside analogues was developed, starting from 3-nitropyran-2-one N-functionalized amidines. Primary amines were reacted with amidines yielding 4-nitromethylene-1,4-dihydropyrimidine derivatives. In an initial survey, several 4-nitromethylene-1,4-dihydropyrimidines turned into 4-nitromethylene-1,2,3,4-tetrahydropyrimidine derivatives under different reduction

  从3-硝基吡喃-2-酮N-官能化am开始，开发了作为嘧啶核苷类似物的4-硝基亚甲基-1,4-二氢嘧啶衍生物。使伯胺与am反应，得到4-硝基亚甲基-1,4-二氢嘧啶衍生物。在初步调查中，几种4-硝基亚甲基-1,4-二氢嘧啶在不同的还原条件下转变为4-硝基亚甲基1,2,3,4-四氢嘧啶衍生物。由于分子内氢键，还原反应还引起环外双键构型从（E）变化为（Z）。
• Boranes in Synthesis. 1. Asymmetric synthesis of β-amino alcohols. A facile conversion of enamines to the corresponding β-amino alcohols in high enantiomeric purity
  作者：Gary B. Fisher、Christian T. Goralski、Lawrence W. Nicholson、Bakthan Singaram

  DOI：10.1016/s0040-4039(00)61541-1

  日期：1993.11

  The asymmetric hydroboration of aldehyde enamines with dIpc2BH at 0 °C, followed by oxidation with NaOH(s)/H2O2, yields the corresponding β-amino alcohols in good yields and high enantiomeric excess.

  醛烯胺与d Ipc 2 BH在0°C下不对称氢硼化，然后用NaOH / H 2 O 2氧化，得到相应的β-氨基醇，收率高，对映体过量高。
• 3-Nitrocoumarin Amidines: A New Synthetic Strategy for Substituted [1]Benzopyrano[3,4-d]imidazol-4(3H)-ones
  作者：Egle M. Beccalli、Alessandro Contini、Pasqualina Trimarco

  DOI：10.1002/ejoc.200300109

  日期：2003.10

  A new synthesis of substituted [1]benzopyrano[3,4-d]imidazol-4(3H)-ones, starting from 3-nitrocoumarin N-functionalized amidines 3, has been developed. When the 3-nitro-amidines 3 were treated with NaBH4 in the presence of 10% palladium on charcoal, 2-substituted [1]benzopyrano[3,4-d]imidazol-4(3H)-ones 4 were produced. Structure elucidation of compounds 4 revealed that they exist as one of the three

  一种新的取代 [1] 苯并吡喃并 [3,4-d] 咪唑-4(3H)-酮的合成方法，从 3-硝基香豆素 N-功能化脒 3 开始，已被开发出来。当在 10% 钯炭存在下用 NaBH4 处理 3-硝基脒 3 时，产生了 2-取代的 [1] 苯并吡喃并 [3,4-d] 咪唑-4(3H)-酮 4。化合物 4 的结构解析表明它们作为三种可能的互变异构结构之一（即 4dα）存在。4d 烷基化得到 6，以及对 6 的 NOE 实验和能量计算允许鉴定 4 种衍生物的最有利结构。或者，通过亚磷酸三乙酯还原 3-硝基脒 3，通过氮烯中间体、环化和 [1.5] σ 移位，产生 2-吗啉代-3-烷基-[1] 苯并吡喃 [3,4-d]咪唑-4(3H)-酮 7.
• 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。