cis-α-Nitro-β-(N-morpholino)stilbene | 128534-71-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: cis-α-Nitro-β-(N-morpholino)stilbene
• 英文别名: (Z)-α-Morpholino-β-nitrostilbene；cis-α-nitro-β-morpholinostilbene；(Z)-2-Morpholino-1-nitro-1,2-diphenylethene；2-morpholino-1-nitro-1,2-diphenylethene；4-[(Z)-2-nitro-1,2-diphenylethenyl]morpholine
• CAS: 128534-71-4
• 化学式: C₁₈H₁₈N₂O₃
• 分子量: 310.353
• InChiKey: KDVSIGSSTJQATR-ZCXUNETKSA-N

物化性质

• 熔点：
  204-205 °C
• 沸点：
  444.9±45.0 °C(Predicted)
• 密度：
  1.225±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  cis-α-Nitro-β-(N-morpholino)stilbene 在 一水合肼 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 0.33h， 以70%的产率得到1,2-dihydrazin-1,2-diphenylethene
  参考文献：
  名称：

  1,2-二硝基-和1-硝基-2-硫代乙烯与肼反应的特定特征

  摘要：

  DOI：

  10.1023/b:rujo.0000010199.56110.ab
• 作为产物：
  描述：

  吗啉 、 cis-1,2-dinitrostilbene 以 正己烷 为溶剂， 生成 cis-α-Nitro-β-(N-morpholino)stilbene
  参考文献：
  名称：

  Kinetics and mechanism of reaction of cis-?,?-dinitrostilbene with morpholine

  摘要：

  Reaction of cis-alpha,beta-dinitrostilbene (substrate) with morpholine (reagent) in n-hexane leads to cis-alpha-nitro-beta-morpholinostilbene (end product). The process is of first order with respect to the substrate and second order with respect to the reagent. Possible reaction mechanisms are analyzed, and it is established that the following are most probable on the basis of kinetic patterns and stereochemistry: development of a charge transfer complex having a hydrogen bond between the substrate nitro group and reagent amino group; reaction of the complex with a second reagent molecule and formation of a carbanion (this stage determines the overall reaction rate); and detachment of a nitrite ion from the nitrocarbanion and its protonation to form the end product.

  DOI：

  10.1007/bf00863913

文献信息

• Stereochemistry in Nucleophilic Vinylic Substitution of Activated Nitro Olefins
  作者：Kyong Pae Park、Hyun-Joon Ha

  DOI：10.1246/bcsj.63.3006

  日期：1990.10

  Each of E and Z-isomers of activated α,β-dinitro olefins and α-iodo-β-nitrostilbene reacted ith several different types of nucleophiles such as amines, thiocyanate, and p-toluenethiolate. Only Z-isomers of vinylic-substituted olefins with amines and thiocyanate were observed as products due to the attractive interactions between the nitro group of substrate and the nucleophile in the intermediate state

  活化的 α,β-二硝基烯烃和 α-碘-β-硝基二苯乙烯的 E 和 Z 异构体中的每一种都与几种不同类型的亲核试剂反应，如胺、硫氰酸盐和对甲苯硫醇盐。由于底物的硝基与中间状态的亲核试剂之间的吸引力相互作用，仅观察到带有胺和硫氰酸酯的乙烯基取代烯烃的 Z-异构体作为产物。p-Toluenethiolate 作为亲核试剂不能产生足够强的相互作用以产生单个 Z 产物，而是产生收敛的 (E) 和 (Z) 产物混合物。尽管如此，还是倾向于 Z 型配置。
• ——
  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.
• 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：——
• ?-Iodo-?-nitrostilbene in the reaction with morpholine and piperidine
  作者：Z. V. Todres、D. S. Ermekov

  DOI：10.1007/bf00864548

  日期：1992.5

  The reaction of alpha-iodo-beta-nitrostilbene with morpholine or piperidine yields alpha-nitro-beta-morpholino- or alpha-nitro-beta-piperidinostilbene. The reaction is regioselective and stereospecific: only the iodine, and not the nitro group, is substituted, the product obtained has a cis structure regardless of whether the initial substrate had a cis- or a transconfiguration. The prereaction stage probably includes the formation of a charge-transfer complex between substrate and reagent.
• Specific Features of Reaction between 1,2-Dinitro- and 1-Nitro-2-Thioethenes and Hydrazine
  作者：T. Yu. Kretser、N. V. Kuz'mina、E. S. Lipina、G. A. Berkova、V. M. Berestovitskaya

  DOI：10.1023/b:rujo.0000010199.56110.ab

  日期：2003.8