[(2S,3S)-3-(benzylcarbamoyl)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(4-methoxyphenyl)-4-oxoazetidin-3-yl] 2-bromoacetate | 1393596-14-9

• 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: [(2S,3S)-3-(benzylcarbamoyl)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(4-methoxyphenyl)-4-oxoazetidin-3-yl] 2-bromoacetate
• CAS: 1393596-14-9
• 化学式: C₂₅H₂₇BrN₂O₇
• 分子量: 547.403
• InChiKey: LPMZZPMSYPTIHY-QVNIBDNGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [(2S,3S)-3-(benzylcarbamoyl)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(4-methoxyphenyl)-4-oxoazetidin-3-yl] 2-bromoacetate 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以52 mg的产率得到(1S,4S)-8-benzyl-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-(4-methoxyphenyl)-5-oxa-2,8-diazaspiro[3.5]nonane-3,6,9-trione
  参考文献：
  名称：

  Regio- and Diastereoselective Synthesis of β-Lactam-Triazole Hybrids via Passerini/CuAAC Sequence

  摘要：

  Passerini (P-3CR) and Passerini-Smiles reactions were investigated in azetidine-2,3-diones, affording the corresponding 3,3-disubstituted-beta-lactams with complete diastereoselectivity in high yields. The study has been carried out using different isocyanides, carboxylic acids, and phenols showing the scope of both reactions. In addition, the regioselective synthesis of highly functionalized beta-lactam-triazole hybrids has been developed via a Passerini/CuAAC sequence. Interestingly, the use of dialkynes/diazides or trialkynes/triazides as linkers in the CuAAC step has allowed the synthesis of C-2 and C-3 symmetric beta-lactam-triazole hybrids, respectively.

  DOI：

  10.1021/jo301113g
• 作为产物：
  描述：

  苄异腈 、 溴乙酸 、 (S)-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(4-methoxyphenyl)azetidine-2,3-dione 以 二氯甲烷 为溶剂， 反应 1.5h， 以49%的产率得到[(2S,3S)-3-(benzylcarbamoyl)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(4-methoxyphenyl)-4-oxoazetidin-3-yl] 2-bromoacetate
  参考文献：
  名称：

  Regio- and Diastereoselective Synthesis of β-Lactam-Triazole Hybrids via Passerini/CuAAC Sequence

  摘要：

  Passerini (P-3CR) and Passerini-Smiles reactions were investigated in azetidine-2,3-diones, affording the corresponding 3,3-disubstituted-beta-lactams with complete diastereoselectivity in high yields. The study has been carried out using different isocyanides, carboxylic acids, and phenols showing the scope of both reactions. In addition, the regioselective synthesis of highly functionalized beta-lactam-triazole hybrids has been developed via a Passerini/CuAAC sequence. Interestingly, the use of dialkynes/diazides or trialkynes/triazides as linkers in the CuAAC step has allowed the synthesis of C-2 and C-3 symmetric beta-lactam-triazole hybrids, respectively.

  DOI：

  10.1021/jo301113g

文献信息

• Regio- and Diastereoselective Synthesis of β-Lactam-Triazole Hybrids <i>via</i> Passerini/CuAAC Sequence
  作者：Benito Alcaide、Pedro Almendros、Cristina Aragoncillo、Ricardo Callejo、M. Pilar Ruiz、M. Rosario Torres

  DOI：10.1021/jo301113g

  日期：2012.8.17

  Passerini (P-3CR) and Passerini-Smiles reactions were investigated in azetidine-2,3-diones, affording the corresponding 3,3-disubstituted-beta-lactams with complete diastereoselectivity in high yields. The study has been carried out using different isocyanides, carboxylic acids, and phenols showing the scope of both reactions. In addition, the regioselective synthesis of highly functionalized beta-lactam-triazole hybrids has been developed via a Passerini/CuAAC sequence. Interestingly, the use of dialkynes/diazides or trialkynes/triazides as linkers in the CuAAC step has allowed the synthesis of C-2 and C-3 symmetric beta-lactam-triazole hybrids, respectively.