2-methyl-N-phenylpropan-1-imine oxide | 68702-72-7

• 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: 2-methyl-N-phenylpropan-1-imine oxide
• CAS: 68702-72-7
• 化学式: C₁₀H₁₃NO
• 分子量: 163.219
• InChiKey: URHRZFZRMKVXSO-FLIBITNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  28.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-methyl-N-phenylpropan-1-imine oxide 、 苯乙炔 在 CuI * pyridine potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以26%的产率得到1,3-diphenyl-4-propan-2-ylazetidin-2-one
  参考文献：
  名称：

  Copper-Catalyzed Reaction of Terminal Alkynes with Nitrones. Selective Synthesis of 1-Aza-1-buten-3-yne and 2-Azetidinone Derivatives

  摘要：

  Reaction of arylacetylenes with C,N-diarylnitrones using a catalyst system of CuI-dppe (dppe = 1,2-bis(diphenylphosphino)ethane) in the presence of potassium carbonate in DMF predominantly affords the corresponding 1,2,4-triaryl-1-aza- 1-buten-3-ynes in good yields. In contrast, the catalytic reaction using CuI in the presence of an excess amount of pyridine as the ligand gives 1,3,4-triaryl-2-azetidinones as the major products. The reaction with aliphatic terminal alkynes in place of arylacetylenes produces the latter products irrespective of the catalyst system used. Asymmetric induction is also observed in the reaction of phenylacetylene with alpha,N-diphenylnitrone to give 1,2,4-triphenyl-2-azetidinone in the presence of chiral bisoxazoline-type ligands.

  DOI：

  10.1021/jo00121a018
• 作为产物：
  描述：

  苯基羟胺 、 异丁醛 在 potassium carbonate 作用下， 以 乙醚 为溶剂， 反应 1.0h， 生成 2-methyl-N-phenylpropan-1-imine oxide
  参考文献：
  名称：

  Copper-Catalyzed Reaction of Terminal Alkynes with Nitrones. Selective Synthesis of 1-Aza-1-buten-3-yne and 2-Azetidinone Derivatives

  摘要：

  Reaction of arylacetylenes with C,N-diarylnitrones using a catalyst system of CuI-dppe (dppe = 1,2-bis(diphenylphosphino)ethane) in the presence of potassium carbonate in DMF predominantly affords the corresponding 1,2,4-triaryl-1-aza- 1-buten-3-ynes in good yields. In contrast, the catalytic reaction using CuI in the presence of an excess amount of pyridine as the ligand gives 1,3,4-triaryl-2-azetidinones as the major products. The reaction with aliphatic terminal alkynes in place of arylacetylenes produces the latter products irrespective of the catalyst system used. Asymmetric induction is also observed in the reaction of phenylacetylene with alpha,N-diphenylnitrone to give 1,2,4-triphenyl-2-azetidinone in the presence of chiral bisoxazoline-type ligands.

  DOI：

  10.1021/jo00121a018

文献信息

• Asymmetric Synthesis of β-Lactams through Copper-Catalyzed Alkyne-Nitrone Coupling with a Prolinol-Phosphine Chiral Ligand
  作者：Yurie Takayama、Takaoki Ishii、Hirohisa Ohmiya、Tomohiro Iwai、Martin C. Schwarzer、Seiji Mori、Tohru Taniguchi、Kenji Monde、Masaya Sawamura

  DOI：10.1002/chem.201702070

  日期：2017.6.22

  Prolinol–phosphine chiral ligands enabled highly enantioselective copper‐catalyzed intermolecular alkyne–nitrone coupling (Kinugasa reaction) to produce 1,3,4‐trisubstituted chiral β‐lactams. A high level of enantiocontrol was achieved not only with aryl‐ or alkenylacetylenes but also with alkylacetylenes, which were important but unfavorable substrates in the previously reported protocols. Two‐point

  脯氨醇-膦的手性配体使得高度对映选择性的铜催化的分子间炔-硝基偶联（Kinugasa反应）产生了1,3,4-三取代的手性β-内酰胺。不仅使用芳基或烯基乙炔，而且使用烷基乙炔都可以实现高水平的对映体控制，这在先前报道的方案中是重要的但不利的底物。提出了由OH-H···O和C（sp 3）-H··· O的氢键构成的手性配体与氮氧阴离子的两点氢键。
• A convenient route to azetidine-2,3-diones and cis-3β-amido azetidinones
  作者：Joseph J. Tufariello、Donald J.P. Pinto、Arnold S. Milowsky、Daniel V. Reinhardt

  DOI：10.1016/s0040-4039(00)96759-5

  日期：1987.1

  The synthesis of 3β-amido azetidinones, 8a and 8b, via azetidine-2,3-diones is described.

  描述了通过氮杂环丁烷-2，3-二酮合成3β-酰胺基氮杂环丁酮8a和8b。
• Gilbertson, Scott R.; Dawson, David P.; Lopez, Omar D., Journal of the American Chemical Society, 1995, vol. 117, # 15, p. 4431 - 4432
  作者：Gilbertson, Scott R.、Dawson, David P.、Lopez, Omar D.、Marshall, Kenneth Lee

  DOI：——

  日期：——
• AURICH, H. G.;EIDEL, J.;SCHMIDT, M., CHEM. BER., 1986, 119, N 1, 18-35
  作者：AURICH, H. G.、EIDEL, J.、SCHMIDT, M.

  DOI：——

  日期：——
• TUFARIELLO, JOSEPH J.;PINTO, DONALD J. P.;MILOWSKY, ARNOLD S.;REINHARDT, +, TETRAHEDRON LETT., 28,(1987) N 45, 5481-5484
  作者：TUFARIELLO, JOSEPH J.、PINTO, DONALD J. P.、MILOWSKY, ARNOLD S.、REINHARDT, +

  DOI：——

  日期：——