(3S,4R)-1-N-BOC-3-[(R)-1-methoxyethyl]-4-vinyl-2-azetidinone | 256371-23-0

• 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,4R)-1-N-BOC-3-[(R)-1-methoxyethyl]-4-vinyl-2-azetidinone
• 英文别名: tert-butyl (2R,3S)-2-ethenyl-3-[(1R)-1-methoxyethyl]-4-oxoazetidine-1-carboxylate
• CAS: 256371-23-0
• 化学式: C₁₃H₂₁NO₄
• 分子量: 255.314
• InChiKey: FPZCBMFDPZZJJV-OPRDCNLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  一氧化碳 、 (3S,4R)-1-N-BOC-3-[(R)-1-methoxyethyl]-4-vinyl-2-azetidinone 在 (nbd)Rh+[(η6-C6H5)B-(C6H5)3] 、 氢气 、 (2S,4S)-(-)-2,4-双(二苯基磷)戊烷 作用下， 以 苯 为溶剂， 70.0 ℃ 、8.27 MPa 条件下， 反应 24.0h， 生成 (3S,4R)-tert-butyl 3-[(R)-1-methoxyethyl]-2-oxo-4-[(R)-1-oxopropan-2-yl]azetidine-1-carboxylate
  参考文献：
  名称：

  Conventional and Tandem Hydroformylation

  摘要：

  过渡金属催化的氢甲酰化已成为合成醛的重要工具。在本文中，我们强调了几种均相和异相钌催化的氢甲酰化的合成应用实例，以及我们实验室开发的将氢甲酰化作为反应步骤的多步骤反应的几个实例。

  DOI：

  10.1055/s-0030-1258169
• 作为产物：
  描述：

  (3S,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl-4-vinyl-2-azetidinone] 在 4-二甲氨基吡啶 、 sodium hydroxide 、 四丁基氟化铵 、 四丁基碘化铵 、 三乙胺 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 17.5h， 生成 (3S,4R)-1-N-BOC-3-[(R)-1-methoxyethyl]-4-vinyl-2-azetidinone
  参考文献：
  名称：

  Regio- and Stereoselective Synthesis of Key 1-Methyl Carbapenem Intermediates via Hydroformylation Using a Zwitterionic Rhodium Catalyst

  摘要：

  The asymmetric hydroformylation of a 4-vinyl beta-lactam catalyzed by a rhodium catalyst with a chiral phosphine ligand was investigated. The catalytic system consisting of a zwitterionic rhodium catalyst, (NBD)Rh+(C6H5B-Ph3) 4, and (S,S)-2,4 bis(diphenylphosphino)pentane, (S,S)-BDPP, gave branched aldehydes in high regio- and stereoselectivity. The hydroformylated products are key intermediates in the synthesis of 1-methylcarbapenem antibiotics. Using (3S,4R)-3-[(R)-1-(tert-butyldimethyl-silyloxy)ethyl]-4-vinyl-2-azetidinone (5a) as the reactant afforded aldehydes in a 97:3 branched-to-linear ratio and 91:9 to beta- to alpha-branched isomers. The regio (branched/linear)- and stereoselectivity (beta/alpha) was >99:1 when (3S,4R)-1-N-BOC-3-[(R)-1-methoxyerhyl]-4-vinyl-2-azetidinone was used as the substrate (5q).

  DOI：

  10.1021/ja993080j

文献信息

• Conventional and Tandem Hydroformylation
  作者：Howard Alper、Maksym Vasylyev

  DOI：10.1055/s-0030-1258169

  日期：2010.9

  Transition-metal-catalyzed hydroformylation has become an essential tool for the synthesis of aldehydes. In this paper, we highlight several examples of synthetically useful applications of homogeneous and heterogeneous rhodium-catalyzed hydroformylation, as well as several examples of tandem processes involving hydroformylation as a reaction step developed in our laboratory.

  过渡金属催化的氢甲酰化已成为合成醛的重要工具。在本文中，我们强调了几种均相和异相钌催化的氢甲酰化的合成应用实例，以及我们实验室开发的将氢甲酰化作为反应步骤的多步骤反应的几个实例。
• Regio- and Stereoselective Synthesis of Key 1-Methyl Carbapenem Intermediates via Hydroformylation Using a Zwitterionic Rhodium Catalyst
  作者：H. S. Park、E. Alberico、H. Alper

  DOI：10.1021/ja993080j

  日期：1999.12.1

  The asymmetric hydroformylation of a 4-vinyl beta-lactam catalyzed by a rhodium catalyst with a chiral phosphine ligand was investigated. The catalytic system consisting of a zwitterionic rhodium catalyst, (NBD)Rh+(C6H5B-Ph3) 4, and (S,S)-2,4 bis(diphenylphosphino)pentane, (S,S)-BDPP, gave branched aldehydes in high regio- and stereoselectivity. The hydroformylated products are key intermediates in the synthesis of 1-methylcarbapenem antibiotics. Using (3S,4R)-3-[(R)-1-(tert-butyldimethyl-silyloxy)ethyl]-4-vinyl-2-azetidinone (5a) as the reactant afforded aldehydes in a 97:3 branched-to-linear ratio and 91:9 to beta- to alpha-branched isomers. The regio (branched/linear)- and stereoselectivity (beta/alpha) was >99:1 when (3S,4R)-1-N-BOC-3-[(R)-1-methoxyerhyl]-4-vinyl-2-azetidinone was used as the substrate (5q).