N-acetyl-N-(4-methoxybenzyl)-L-phenylalanylglycine | 1334240-45-7

• 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-acetyl-N-(4-methoxybenzyl)-L-phenylalanylglycine
• CAS: 1334240-45-7
• 化学式: C₂₁H₂₄N₂O₅
• 分子量: 384.432
• InChiKey: NCDLJHIGGUFGOQ-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.86
• 重原子数：
  28.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  95.94
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-乙酰氧基苯甲醛 、 N-acetyl-N-(4-methoxybenzyl)-L-phenylalanylglycine 、 甲胺 在 N,N'-二环己基碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 19.0h， 以150 mg的产率得到(4Z)-2-[(1S)-1-(N-acetyl-N-(4-methoxybenzyl))amino-2-phenylethyl]-1-methyl-4-(4-hydroxybenzylidene)-4,5-dihydro-1H-imidazol-5-one
  参考文献：
  名称：

  Synthesis of biosynthetic precursors of chromophores of red fluorescent proteins

  摘要：

  A method for the synthesis of 5-arylidene-3,5-dihydro-4H-imidazol-4-ones corresponding to the chromophore of the green fluorescent protein ( GFP) with acylaminoalkyl substituents at position 2 of the imidazolone core has been developed. These biomimetic model compounds are the precursors of the chromophores of red fluorescent proteins. The method is based on the masking of the dehydrotyrosine fragment of target compounds by the beta-hydroxytyrosine moiety. The key stages of the synthesis include the condensation of beta-hydroxytyrosine with the appropriate N-acetylamino acid, the unmasking of dehydrotyrosine by O-acylation with subsequent elimination, and the cyclization of the resulting 3-acylaminocinnamic acid derivatives in basic medium.

  DOI：

  10.1134/s1068162011040066
• 作为产物：
  描述：

  N-(4-methoxybenzyl)-L-phenylalanine 在 三乙胺 、 N,N'-二环己基碳二亚胺 、 sodium hydroxide 作用下， 以 氯仿 为溶剂， 反应 24.0h， 生成 N-acetyl-N-(4-methoxybenzyl)-L-phenylalanylglycine
  参考文献：
  名称：

  Synthesis of biosynthetic precursors of chromophores of red fluorescent proteins

  摘要：

  A method for the synthesis of 5-arylidene-3,5-dihydro-4H-imidazol-4-ones corresponding to the chromophore of the green fluorescent protein ( GFP) with acylaminoalkyl substituents at position 2 of the imidazolone core has been developed. These biomimetic model compounds are the precursors of the chromophores of red fluorescent proteins. The method is based on the masking of the dehydrotyrosine fragment of target compounds by the beta-hydroxytyrosine moiety. The key stages of the synthesis include the condensation of beta-hydroxytyrosine with the appropriate N-acetylamino acid, the unmasking of dehydrotyrosine by O-acylation with subsequent elimination, and the cyclization of the resulting 3-acylaminocinnamic acid derivatives in basic medium.

  DOI：

  10.1134/s1068162011040066