2-nitromethyl-4-oxo-4-phenyl-butyric acid methyl ester | 304887-56-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-nitromethyl-4-oxo-4-phenyl-butyric acid methyl ester
• 英文别名: α-Nitro-δ-oxo-δ-phenyl-butan-β-carbonsaeuremethylester；β'-Nitro-β-benzoyl-isobuttersaeuremethylester；β-Nitro-α-phenacyl-propionsaeuremethylester；2-Nitromethyl-4-oxo-4-phenyl-buttersaeure-methylester；Methyl 2-(nitromethyl)-4-oxo-4-phenylbutanoate
• CAS: 304887-56-7
• 化学式: C₁₂H₁₃NO₅
• 分子量: 251.239
• InChiKey: DDLBSDBZMHBYMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  89.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-nitromethyl-4-oxo-4-phenyl-butyric acid methyl ester 在 氟化铵 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 methyl (Z)-anti-2-(hydroxyiminomethyl)-4-oxo-4-phenylbut-2-enoate
  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：

  3-苯基丙酸甲酯 在 甲醇 、 氯仿 作用下， 生成 2-nitromethyl-4-oxo-4-phenyl-butyric acid methyl ester
  参考文献：
  名称：

  Kohler, Engelbrecht, Journal of the American Chemical Society, 1919, vol. 41, p. 766

  摘要：

  DOI：

文献信息

• Synthesis of β-Functionalized α,β-Unsaturated Oximes via Silylation of Nitro Compounds
  作者：Vitaly M. Danilenko、Alexander A. Tishkov、Sema L. Ioffe、Ilya M. Lyapkalo、Yury A. Strelenko、Vladimir A. Tartakovsky

  DOI：10.1055/s-2002-23539

  日期：——

  A general method for the synthesis of conjugated enoximes 2 via silylation of functionalized aliphatic nitro compounds 1 has been claborated. The configuration of obtained products has been determined by NMR spectroscopy.

  已经制定了通过官能化脂肪族硝基化合物 1 的甲硅烷基化合成共轭酶肟 2 的通用方法。所得产物的构型已通过核磁共振光谱确定。
• Synthesis of N,N-bis(silyloxy)enamines with a functionalized double bond
  作者：Alexander D. Dilman、Alexander A. Tishkov、Il’ya M. Lyapkalo、Sema L. Ioffe、Vadim V. Kachala、Yury A. Strelenko、Vladimir A. Tartakovsky

  DOI：10.1039/b004268o

  日期：——

  The general method for the double silylation of α- or β-functionalized aliphatic nitro compounds 1 leading to regio- and stereoselective formation of N,N-bis(silyloxy)enamines 3 with a functionalized double bond is elaborated. The configuration of obtained products is determined by NMR spectroscopy.

  详细阐述了 α- 或 β-官能化脂肪族硝基化合物 1 双硅烷基化，从而形成具有官能化双键的 N,N-双（硅烷氧基）烯胺 3 的区域和立体选择性的一般方法。 所获产物的构型由核磁共振光谱确定。
• Rice, Journal of the American Chemical Society, 1923, vol. 45, p. 231
  作者：Rice

  DOI：——

  日期：——