Tert-butyl 2-oxo-1-azaspiro[3.4]octane-1-carboxylate | 204132-38-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环丁烷
• 英文名称: Tert-butyl 2-oxo-1-azaspiro[3.4]octane-1-carboxylate
• CAS: 204132-38-7
• 化学式: C₁₂H₁₉NO₃
• 分子量: 225.288
• InChiKey: QQHXHYOTDZRDSM-UHFFFAOYSA-N

物化性质

• 熔点：
  64-65 °C
• 沸点：
  360.8±11.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  L-亮氨酸苄基酯 、 Tert-butyl 2-oxo-1-azaspiro[3.4]octane-1-carboxylate 在 potassium cyanide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以98%的产率得到benzyl (2S)-4-methyl-2-[[2-[1-[(2-methylpropan-2-yl)oxycarbonylamino]cyclopentyl]acetyl]amino]pentanoate
  参考文献：
  名称：

  A Concise β-Lactam Route to Short Peptide Segments Containing β,β-Disubstituted β-Amino Acids

  摘要：

  An efficient epimerization-free route toward beta,beta-disubstituted beta-amino acid-containing peptides is described. The methodology involves the use of 4,4-disubstituted-N-Boc beta-lactams as acylating agents, which upon coupling with amino acid esters, promoted by potassium cyanide, give rise to dipeptides with no appreciable racemization. By this procedure short peptide segments containing a four-, five-, or six-membered ring at the beta-position of the beta-amino acid residue have been prepared. The method has also proven to be valuable for the preparation of tripeptides. In addition the sterically hindered amino terminus of the beta-amino acid can undergo peptide couplings under standard conditions.

  DOI：

  10.1021/jo9712862
• 作为产物：
  描述：

  氯磺酰异氰酸酯 、 亚甲基环戊烷 、 二碳酸二叔丁酯 生成 tert-butyl 5-methyl-7-oxo-6-azabicyclo[3.2.0]heptane-6-carboxylate 、 Tert-butyl 2-oxo-1-azaspiro[3.4]octane-1-carboxylate
  参考文献：
  名称：

  A Concise β-Lactam Route to Short Peptide Segments Containing β,β-Disubstituted β-Amino Acids

  摘要：

  An efficient epimerization-free route toward beta,beta-disubstituted beta-amino acid-containing peptides is described. The methodology involves the use of 4,4-disubstituted-N-Boc beta-lactams as acylating agents, which upon coupling with amino acid esters, promoted by potassium cyanide, give rise to dipeptides with no appreciable racemization. By this procedure short peptide segments containing a four-, five-, or six-membered ring at the beta-position of the beta-amino acid residue have been prepared. The method has also proven to be valuable for the preparation of tripeptides. In addition the sterically hindered amino terminus of the beta-amino acid can undergo peptide couplings under standard conditions.

  DOI：

  10.1021/jo9712862

文献信息

• A Concise β-Lactam Route to Short Peptide Segments Containing β,β-Disubstituted β-Amino Acids
  作者：Claudio Palomo、Mikel Oiarbide、Simona Bindi

  DOI：10.1021/jo9712862

  日期：1998.4.1

  An efficient epimerization-free route toward beta,beta-disubstituted beta-amino acid-containing peptides is described. The methodology involves the use of 4,4-disubstituted-N-Boc beta-lactams as acylating agents, which upon coupling with amino acid esters, promoted by potassium cyanide, give rise to dipeptides with no appreciable racemization. By this procedure short peptide segments containing a four-, five-, or six-membered ring at the beta-position of the beta-amino acid residue have been prepared. The method has also proven to be valuable for the preparation of tripeptides. In addition the sterically hindered amino terminus of the beta-amino acid can undergo peptide couplings under standard conditions.