(3S,4S)-3-pentyl-1,4-diphenylazetidin-2-one | 1380590-96-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (3S,4S)-3-pentyl-1,4-diphenylazetidin-2-one
• CAS: 1380590-96-4
• 化学式: C₂₀H₂₃NO
• 分子量: 293.409
• InChiKey: UXERSUYTIPCXDL-RBUKOAKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-庚炔 、 N-(benzylidene)aniline N-oxide 在 (CuOTf)*toluene 、 (3aR,8bS)-2-[2-[(3aR,8bS)-4,8b-dihydro-3aH-indeno[1,2-d][1,3]oxazol-2-yl]-1-[(4S)-4-tert-butyl-4,5-dihydro-1,3-oxazol-2-yl]propan-2-yl]-4,8b-dihydro-3aH-indeno[1,2-d][1,3]oxazole 、 二环己胺 作用下， 以 乙腈 为溶剂， 反应 11.5h， 生成 (3S,4S)-3-pentyl-1,4-diphenylazetidin-2-one 、 (3R,4R)-3-pentyl-1,4-diphenylazetidin-2-one
  参考文献：
  名称：

  Tris(oxazoline)/copper-catalyzed coupling of alkynes with nitrones: a highly enantioselective access to β-lactams

  摘要：

  Chiral tris(oxazoline)/Cu(I) complexes are demonstrated as a type of efficient catalysts for the asymmetric Kinugasa reaction of terminal alkynes with C-arylnitrones, providing a highly enantio- and diastereoselective access to optically active beta-lactams. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.04.049

文献信息

• Copper-Catalyzed Reaction of Terminal Alkynes with Nitrones. Selective Synthesis of 1-Aza-1-buten-3-yne and 2-Azetidinone Derivatives
  作者：Masahiro Miura、Masahiro Enna、Kazumi Okuro、Masakatsu Nomura

  DOI：10.1021/jo00121a018

  日期：1995.8

  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.
• Tris(oxazoline)/copper-catalyzed coupling of alkynes with nitrones: a highly enantioselective access to β-lactams
  作者：Jiang-Hua Chen、Sai-Hu Liao、Xiu-Li Sun、Qi Shen、Yong Tang

  DOI：10.1016/j.tet.2012.04.049

  日期：2012.6

  Chiral tris(oxazoline)/Cu(I) complexes are demonstrated as a type of efficient catalysts for the asymmetric Kinugasa reaction of terminal alkynes with C-arylnitrones, providing a highly enantio- and diastereoselective access to optically active beta-lactams. (C) 2012 Elsevier Ltd. All rights reserved.