trimethyl(4-nitro-1,3,4-triphenylbut-1-enyloxy)silane

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: trimethyl(4-nitro-1,3,4-triphenylbut-1-enyloxy)silane
• 英文别名: trimethyl-[(Z)-4-nitro-1,3,4-triphenylbut-1-enoxy]silane
• 化学式: C₂₅H₂₇NO₃Si
• 分子量: 417.58
• InChiKey: PLALWGLAMICZBF-CLCOLTQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.68
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  三甲基溴硅烷 、 4-nitro-1,3,4-triphenyl-butan-1-one 在 三乙胺 、 水 作用下， 以 二氯甲烷 、 Petroleum ether 为溶剂， 反应 168.0h， 以51%的产率得到trimethyl(4-nitro-1,3,4-triphenylbut-1-enyloxy)silane
  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

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.