(E)-2-Morpholino-1-nitro-1-phenylethene | 591251-70-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-2-Morpholino-1-nitro-1-phenylethene
• 英文别名: (e)-2-Morpholino-1-nitro-1-phenyl-ethene；4-[(E)-2-nitro-2-phenylethenyl]morpholine
• CAS: 591251-70-6
• 化学式: C₁₂H₁₄N₂O₃
• 分子量: 234.255
• InChiKey: QKFXEPZSXAQHDN-ZRDIBKRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  58.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,3-dihydro-1,3-dimethyl-2-methylene-3-phenyl-1H-indole 、 (E)-2-Morpholino-1-nitro-1-phenylethene 在 cerium(III) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 360.0h， 以26%的产率得到(1'E,2'E)-2,3-dihydro-1,3-dimethyl-3-phenyl-2-[(3'-nitro-3'-phenyl)prop-2-enylidene]-1H-indole
  参考文献：
  名称：

  On the reactivity of some 2-methyleneindolines with β-nitroenamines, α-nitroalkenes, and 1,2-diaza-1,3-butadienes

  摘要：

  A study of the behaviour of some electron-rich 2-methyleneindolines (1-3) with different electron-poor reagents (formation of new carbon-carbon and nitrogen-carbon bonds) has furnished interesting results from both synthetic and the mechanistic viewpoints. Enamines 1-3 have been reacted with the beta-nitroenamines 4-7 (reaction CeCl3 center dot 7H(2)O promoted), giving the polymethine dyes 14-23. The same bases 1-3 have been nitroalkylated with the nitroolefins 8-10, furnishing the indolines 24-32, and the diastereoselectivity of the reaction has been thoroughly investigated. The most unexpected results derived from the first example of reaction of Fischer's bases with 1,2-diaza-1,3-butadienes. In fact, with 11-13, the 'unknown' indoline spirodihydropyrroles 33-40 were formed. Their structures were unambiguously assigned, and we determined, as an example, that of 33 by X-ray analysis. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.04.027
• 作为产物：
  描述：

  吗啉 、 2-(4-chlorophenylthio)-1-nitro-1-phenylethene 以 乙醚 为溶剂， 反应 0.83h， 以75%的产率得到(E)-2-Morpholino-1-nitro-1-phenylethene
  参考文献：
  名称：

  摘要：

  2-Arylthio- and 2-arylsulfonyl-1-nitro-1-phenylethenes react with an-tines to give the corresponding nitroenamines whose configuration (E or Z) depends on the amine structure. Primary amines gives rise to Z-nitroenamines, secondary cyclic amines with 2-arylthio-1-nitroalkenes form E-nitroenaniines, and with more reactive 2-arylsulfonyl-1-nitroalkenes E/Z-isomeric mixtures are obtained.

  DOI：

  10.1023/a:1023494629499

文献信息

• Nitroalkylation and nitroalkenylation reactions of γ-lactone enolates. A facile ring switch from polysubstituted γ-lactones to polysubstituted γ-lactams
  作者：C. Forzato、P. Nitti、G. Pitacco、E. Valentin、S. Morganti、E. Rizzato、D. Spinelli、C. Dell'Erba、G. Petrillo、C. Tavani

  DOI：10.1016/j.tet.2004.07.084

  日期：2004.11

  Michael addition of lithium enolates of gamma-butyrolactone 1 and alpha-methyl-gamma-butyrolactone 1' to (E)-1-nitropropene 2, (E)-beta-nitrostyrene 3 and (E)-2-vitro-1-phenylpropene 4 is described. Reactions of the lithium enolate of 1' with 2 and 4 occurred with high diasteroselectivity (80 and 92% d.e., respectively). Reactions of the zinc enolate of 1' with two beta-nitroenamines and two methylthiosubstituted 1-amino-2-vitro-1,3-dienes were also examined. Catalytic reduction of the nitroalkylated and nitroalkenylated products allowed the achievement of functionalized gamma-lactams and/or cyclic hydroxamic acids. (C) 2004 Elsevier Ltd. All rights reserved.
• Pavlova; Lipina; Kasem, Russian Journal of Organic Chemistry, 1999, vol. 35, # 9, p. 1321 - 1325
  作者：Pavlova、Lipina、Kasem、Kuz'mina

  DOI：——

  日期：——
• ——
  作者：N. V. Kuz'mina

  DOI：10.1023/a:1023494629499

  日期：——

  2-Arylthio- and 2-arylsulfonyl-1-nitro-1-phenylethenes react with an-tines to give the corresponding nitroenamines whose configuration (E or Z) depends on the amine structure. Primary amines gives rise to Z-nitroenamines, secondary cyclic amines with 2-arylthio-1-nitroalkenes form E-nitroenaniines, and with more reactive 2-arylsulfonyl-1-nitroalkenes E/Z-isomeric mixtures are obtained.
• On the reactivity of some 2-methyleneindolines with β-nitroenamines, α-nitroalkenes, and 1,2-diaza-1,3-butadienes
  作者：Orazio A. Attanasi、Gianfranco Favi、Paolino Filippone、Cristina Forzato、Gianluca Giorgi、Stefano Morganti、Patrizia Nitti、Giuliana Pitacco、Egon Rizzato、Domenico Spinelli、Ennio Valentin

  DOI：10.1016/j.tet.2006.04.027

  日期：2006.6

  A study of the behaviour of some electron-rich 2-methyleneindolines (1-3) with different electron-poor reagents (formation of new carbon-carbon and nitrogen-carbon bonds) has furnished interesting results from both synthetic and the mechanistic viewpoints. Enamines 1-3 have been reacted with the beta-nitroenamines 4-7 (reaction CeCl3 center dot 7H(2)O promoted), giving the polymethine dyes 14-23. The same bases 1-3 have been nitroalkylated with the nitroolefins 8-10, furnishing the indolines 24-32, and the diastereoselectivity of the reaction has been thoroughly investigated. The most unexpected results derived from the first example of reaction of Fischer's bases with 1,2-diaza-1,3-butadienes. In fact, with 11-13, the 'unknown' indoline spirodihydropyrroles 33-40 were formed. Their structures were unambiguously assigned, and we determined, as an example, that of 33 by X-ray analysis. (c) 2006 Elsevier Ltd. All rights reserved.