Tert-butyl 3-chloro-2-oxo-1-azaspiro[3.3]heptane-1-carboxylate | 204132-42-3

• 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 3-chloro-2-oxo-1-azaspiro[3.3]heptane-1-carboxylate
• CAS: 204132-42-3
• 化学式: C₁₁H₁₆ClNO₃
• 分子量: 245.706
• InChiKey: JRXWXYRTUUAXBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  Tert-butyl 3-chloro-2-oxo-1-azaspiro[3.3]heptane-1-carboxylate 在 palladium on activated charcoal potassium cyanide 、 氢气 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 生成 (2S)-4-methyl-2-[[2-[1-[(2-methylpropan-2-yl)oxycarbonylamino]cyclobutyl]acetyl]amino]pentanoic acid
  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：

  亚甲基环丁烷 在 4-二甲氨基吡啶 、 氢氧化钾 、 对甲苯磺酰氯 、 sodium sulfite 、 lithium diisopropyl amide 作用下， 以 乙醚 、 水 、 乙腈 为溶剂， 反应 1.5h， 生成 Tert-butyl 3-chloro-2-oxo-1-azaspiro[3.3]heptane-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.