2-[N,N-bis(trimethylsilyloxy)amino]-3-(4-methoxyphenyl)-5-(4-tolyl)-2,3-dihydrofuran

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-[N,N-bis(trimethylsilyloxy)amino]-3-(4-methoxyphenyl)-5-(4-tolyl)-2,3-dihydrofuran
• 英文别名: (2S,3R)-3-(4-methoxyphenyl)-5-(4-methylphenyl)-N,N-bis(trimethylsilyloxy)-2,3-dihydrofuran-2-amine
• 化学式: C₂₄H₃₅NO₄Si₂
• 分子量: 457.717
• InChiKey: DZQQRBYTFPTSFB-VWNXMTODSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.32
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  40.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[N,N-bis(trimethylsilyloxy)amino]-3-(4-methoxyphenyl)-5-(4-tolyl)-2,3-dihydrofuran 在 氟化铵 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以51%的产率得到4-(4-methoxyphenyl)-2-(4-tolyl)furan
  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：

  三甲基溴硅烷 、 3-(4-甲氧基苯基)-1-(4-甲基苯基)-4-硝基-1-丁酮 在 三乙胺 、 水 作用下， 以 二氯甲烷 、 Petroleum ether 为溶剂， 反应 168.0h， 以92%的产率得到2-[N,N-bis(trimethylsilyloxy)amino]-3-(4-methoxyphenyl)-5-(4-tolyl)-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

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.