N-(tert-butoxycarbonyl)-4-[(13)C-cyano]-L-phenylalanine methyl ester | 1348705-06-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(tert-butoxycarbonyl)-4-[(13)C-cyano]-L-phenylalanine methyl ester
• 英文别名: methyl (2S)-3-[4-(azanylidyne(113C)methyl)phenyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 1348705-06-5
• 化学式: C₁₆H₂₀N₂O₄
• 分子量: 305.335
• InChiKey: AUVCCKINWBIXOP-AMQTZIGVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  88.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  Boc-L-酪氨酸甲酯 在 吡啶 、 dibromobis(triphenylphosphine)nickel(II) 、 三苯基膦 、 锌 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.2h， 生成 N-(tert-butoxycarbonyl)-4-[(13)C-cyano]-L-phenylalanine methyl ester
  参考文献：
  名称：

  Synthesis of isotopomers of N-(tert-butoxycarbonyl)-4-cyano-l-phenylalanine methyl ester: choice of cyanation solvent

  摘要：

  N-(tert-butoxycarbonyl)-4-cyano-L-phenylalanine methyl ester and three isotopomers ((CN)-N-15, (CN)-C-13, and (CN)-C-13-N-15) were successfully synthesized in two steps to expand the utility of the nitrile symmetric stretch vibration of this modified amino acid as a vibrational reporter of local environments. The choice of cyanation solvent directly impacted the level of isotopic enrichment of the isotopomers. The commonly used solvent acetonitrile resulted in an isotopic enrichment of only similar to 80% with a cyanation reaction time of 4.5 h, however, the cyanation solvent N,N-dimethylformamide afforded the isotopomers with >98% isotopic enrichment. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.10.050

文献信息

• Synthesis of isotopomers of N-(tert-butoxycarbonyl)-4-cyano-l-phenylalanine methyl ester: choice of cyanation solvent
  作者：Christopher G. Bazewicz、Jacob S. Lipkin、Kristen A. Lozinak、Matthew D. Watson、Scott H. Brewer

  DOI：10.1016/j.tetlet.2011.10.050

  日期：2011.12

  N-(tert-butoxycarbonyl)-4-cyano-L-phenylalanine methyl ester and three isotopomers ((CN)-N-15, (CN)-C-13, and (CN)-C-13-N-15) were successfully synthesized in two steps to expand the utility of the nitrile symmetric stretch vibration of this modified amino acid as a vibrational reporter of local environments. The choice of cyanation solvent directly impacted the level of isotopic enrichment of the isotopomers. The commonly used solvent acetonitrile resulted in an isotopic enrichment of only similar to 80% with a cyanation reaction time of 4.5 h, however, the cyanation solvent N,N-dimethylformamide afforded the isotopomers with >98% isotopic enrichment. (C) 2011 Elsevier Ltd. All rights reserved.