3-Benzoyl-2,3-diphenylnitropropan | 4983-78-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 3-Benzoyl-2,3-diphenylnitropropan
• 英文别名: 4-Nitro-1,2,3-triphenylbutan-1-one
• CAS: 4983-78-2
• 化学式: C₂₂H₁₉NO₃
• 分子量: 345.398
• InChiKey: KRVOIZXLPAEPOT-UHFFFAOYSA-N

物化性质

• 沸点：
  520.2±50.0 °C(Predicted)
• 密度：
  1.192±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  62.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  三甲基溴硅烷 、 3-Benzoyl-2,3-diphenylnitropropan 在 三乙胺 、 水 作用下， 以 二氯甲烷 、 Petroleum ether 为溶剂， 反应 336.0h， 以51%的产率得到2-[N,N-bis(trimethylsilyloxy)amino]-3,4,5-triphenyl-2,3-dihydrofuran
  参考文献：
  名称：

  摘要：

  Silylation of gamma-nitro ketones of the general formula (RCOCH)-C-1(R-2)CH(R-3)CH(R-4)NO2 proceeded stereoselectively to give 2-[N,N-bis(trimethylsilyloxy)amino]-2,3-dihydrofurans, conjugated enoximes, silylation products of the carbonyl group or both functional groups, or N, N-bis(trimethylsilyloxy)enamine depending on the nature and positions of the substituents in the carbon skeleton. Dihydrofuran derivatives are formed for R-1 = Ar or cyclo-C3H5. Enoximes are generated as the silylation products of the starting ketones with enhanced P-proton mobility (R-3 CO2Me or 4-NO2C6H4). The presence of an alkyl group at the carbonyl function (R-1 = Alk) is favorable for the formation of enoximes. Finally, the introduction of a substituent at the a position with respect to the nitro group (R-4 = Me, CO2Me, or Ph) leads to the formation of silyl enolates. Under the action of NH4F in MeOH, dihydrofurans can be transformed into substituted furans in moderate yields.

  DOI：

  10.1023/a:1023958806825
• 作为产物：
  描述：

  β-硝基苯乙烯 、 1-morpholino-1,2-diphenylethene 生成 3-Benzoyl-2,3-diphenylnitropropan
  参考文献：
  名称：

  Reaction of Enamines with Nitro Olefins¹

  摘要：

  DOI：

  10.1021/jo01023a066

文献信息

• ——
  作者：K. P. Birin

  DOI：10.1023/a:1023958806825

  日期：——

  Silylation of gamma-nitro ketones of the general formula (RCOCH)-C-1(R-2)CH(R-3)CH(R-4)NO2 proceeded stereoselectively to give 2-[N,N-bis(trimethylsilyloxy)amino]-2,3-dihydrofurans, conjugated enoximes, silylation products of the carbonyl group or both functional groups, or N, N-bis(trimethylsilyloxy)enamine depending on the nature and positions of the substituents in the carbon skeleton. Dihydrofuran derivatives are formed for R-1 = Ar or cyclo-C3H5. Enoximes are generated as the silylation products of the starting ketones with enhanced P-proton mobility (R-3 CO2Me or 4-NO2C6H4). The presence of an alkyl group at the carbonyl function (R-1 = Alk) is favorable for the formation of enoximes. Finally, the introduction of a substituent at the a position with respect to the nitro group (R-4 = Me, CO2Me, or Ph) leads to the formation of silyl enolates. Under the action of NH4F in MeOH, dihydrofurans can be transformed into substituted furans in moderate yields.
• Reaction of Enamines with Nitro Olefins¹
  作者：Martin E. Kuehne、Louise Foley

  DOI：10.1021/jo01023a066

  日期：1965.12