[(2S,3S)-3-(benzylcarbamoyl)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(4-methoxyphenyl)-4-oxoazetidin-3-yl] 2-azidobenzoate | 1393596-06-9

• 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-azidobenzoate
• CAS: 1393596-06-9
• 化学式: C₃₀H₂₉N₅O₇
• 分子量: 571.59
• InChiKey: QENUJLSWZMHQMD-GVQINVNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  42
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  9

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-azidobenzoate 、 1,2-Bis-prop-2-ynyloxymethyl-benzene 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 以88 mg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-[4-[[2-[[1-[2-[(2S,3S)-3-(benzylcarbamoyl)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(4-methoxyphenyl)-4-oxoazetidin-3-yl]oxycarbonylphenyl]triazol-4-yl]methoxymethyl]phenyl]methoxymethyl]triazol-1-yl]benzoate
  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：

  2-叠氮苯甲酸 、 苄异腈 、 (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 16.0h， 以90%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-azidobenzoate
  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.