β-nitro-β-phenoxy-α-phenylstyrene | 97807-45-9

• 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: β-nitro-β-phenoxy-α-phenylstyrene
• 英文别名: 1-nitro-1-phenoxy-2,2-diphenylethylene；(2-Nitro-2-phenoxy-1-phenylethenyl)benzene
• CAS: 97807-45-9
• 化学式: C₂₀H₁₅NO₃
• 分子量: 317.344
• InChiKey: DAZHVEOHGCNDFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  丙基溴化镁 、 β-nitro-β-phenoxy-α-phenylstyrene 反应 0.17h， 生成 1-nitro-1-phenoxy-2,2-diphenylpentane
  参考文献：
  名称：

  β-硝基苯乙烯与格利雅（Grignard）或有机锂试剂的反应生成硝基烷，羟肟基卤化物和一氧化氮

  摘要：

  β型硝基苯乙烯1或2与格氏或有机锂试剂反应在乙醚或THF溶液由1,4-加成中间nitronates以产生甲。当用稀盐酸处理A时，获得高产率的硝基烷3（和肟4）或5。当将中间体A缓慢加入到冰冷的浓氢卤酸中时，可以分离出羟甲酰卤6、8或一氧化氮7。如果从基材1a产生的硝酸盐观察到相同的产物6和/或7。将β-硝基苯乙烯2加入到85％的H 2 SO 4水溶液中，但是当β-硝基苯乙烯2与格氏试剂反应并在相同条件下进行后处理时，仅产生水解的羧酸9。腈氧化物7可与烯烃或炔烃进行1，3-偶极环加成反应以生成2-异恶唑啉或异恶唑。据报道，通过分子内一氧化氮-烯烃环加成反应可以一锅合成[n，3,0]双环（n = 3或4）化合物23-27。

  DOI：

  10.1016/s0040-4020(97)10356-8
• 作为产物：
  描述：

  1,1-diphenyl-2,2-dinitroethylene 、 potassium phenolate 以49%的产率得到
  参考文献：
  名称：

  RUSSELL, G. A.;DEDOLPH, D., J. ORG. CHEM., 1985, 50, N 20, 3878-3881

  摘要：

  DOI：

文献信息

• Reactions of ethyl phosphites with .beta.-nitrostyrenes. The role of nitrosoalkenes as intermediates
  作者：Glen A. Russell、Ching Fa Yao

  DOI：10.1021/jo00050a026

  日期：1992.11

  3-Phenyl-2-substituted-indoles are formed in high yields in the reaction of Ph2C=C(R)NO2 (R = H, Me, Ph) with (EtO)3P at 150-degrees-C while reaction with (EtO)2PO-/(EtO)2P(O)H at room temperature forms the aziridines 1 with R = H, Me, Ph. 2,2-Diphenyl-3-substituted-2H-azirines formed by deoxygenation of the Michael-type adducts are postulated as intermediates. Reactions of PhCH=C(R)NO2 (R = H, Me, Ph) with (EtO)3P at 150-degrees-C or (EtO)2PO-/(EtO)2P(O)H at room temperature give products resulting from the addition of the phosphorus nudeophile at the benzylidene carbon atom. Evidence for the formartion of cyclic structures with pentacoordinated phosphorus atoms is presented for the reaction of Ph2C=C(Me)NO2 with (EtO)2PO-/EtO)2P(O)H and for PhCH=C(R)NO2 (R = H, Me, Ph) with (EtO)3P. The Michael-type adducts PhCH[P(O)(OEt)2]CH(R)NO2 (R = Me, Ph) undergo reaction upon treatment with aqueous base at 80-100-degrees-C followed by acidification to yield the 3-(diethoxyphosphinyl)-2-R-N-hydroxyindoles. 4-(Diethoxyphosphinyl)-3-R-4H-1,2-benzoxazines (13, R = Me, Ph) are formed by reaction with 85% H2SO4 Of the adducts of PhCH=C(R)NO2 with (EtO)2PO (R = Me) or (EtO)3P (R = Ph).