tert-butyl N-[N'-[(2S)-1-(cyclohexylamino)-3-(1H-indol-3-yl)-1-oxopropan-2-yl]-N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]carbamate | 1000312-31-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: tert-butyl N-[N'-[(2S)-1-(cyclohexylamino)-3-(1H-indol-3-yl)-1-oxopropan-2-yl]-N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]carbamate
• CAS: 1000312-31-1
• 化学式: C₂₈H₄₁N₅O₅
• 分子量: 527.664
• InChiKey: KLXRAURPRNSQFG-QFIPXVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  134
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (2S)-2-[bis[(2-methylpropan-2-yl)oxycarbonylamino]methylideneamino]-3-(1H-indol-3-yl)propanoic acid 、 环己胺 在 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以60%的产率得到tert-butyl N-[N'-[(2S)-1-(cyclohexylamino)-3-(1H-indol-3-yl)-1-oxopropan-2-yl]-N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]carbamate
  参考文献：
  名称：

  Convergent and Stereospecific Synthesis of Molecules Containing α-Functionalized Guanidiniums via α-Guanidino Acids

  摘要：

  [Graphics]To introduce chirality and functional groups adjacent to guanidiniums to modulate specificity and affinity in recognition, N,N'-bis(Boc)-alpha-guanidino acids were synthesized from alpha-amino acid methyl esters. Protected alpha-guanidino acids coupled to cyclohexylamine and trans- 1,4-diaminocyclohexane in good yield and with retention of stereochemistry. Boc deprotection was conducted under mild acidic conditions (0.5 M HCl/EtOAc) to minimize epimerization. The deprotected guanidinium is configurationally stable under more acidic conditions. This approach represents a practical, convergent, stereospecific methodology to introduce chiral cc-substituted guanidinium groups into molecules.

  DOI：

  10.1021/jo701766c

文献信息

• Convergent and Stereospecific Synthesis of Molecules Containing α-Functionalized Guanidiniums via α-Guanidino Acids
  作者：Shalini Balakrishnan、Chen Zhao、Neal J. Zondlo

  DOI：10.1021/jo701766c

  日期：2007.12.1

  [Graphics]To introduce chirality and functional groups adjacent to guanidiniums to modulate specificity and affinity in recognition, N,N'-bis(Boc)-alpha-guanidino acids were synthesized from alpha-amino acid methyl esters. Protected alpha-guanidino acids coupled to cyclohexylamine and trans- 1,4-diaminocyclohexane in good yield and with retention of stereochemistry. Boc deprotection was conducted under mild acidic conditions (0.5 M HCl/EtOAc) to minimize epimerization. The deprotected guanidinium is configurationally stable under more acidic conditions. This approach represents a practical, convergent, stereospecific methodology to introduce chiral cc-substituted guanidinium groups into molecules.