N-[(S)-2-{1-[(S)-2-Carbamoyl-1-(3-naphthalen-1-yl-propylcarbamoyl)-ethylcarbamoyl]-cyclohexylcarbamoyl}-6-(diethoxy-phosphoryl)-1,2,3,4-tetrahydro-naphthalen-2-yl]-oxalamic acid tert-butyl ester | 690254-55-8

• 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-[(S)-2-{1-[(S)-2-Carbamoyl-1-(3-naphthalen-1-yl-propylcarbamoyl)-ethylcarbamoyl]-cyclohexylcarbamoyl}-6-(diethoxy-phosphoryl)-1,2,3,4-tetrahydro-naphthalen-2-yl]-oxalamic acid tert-butyl ester
• CAS: 690254-55-8
• 化学式: C₄₅H₆₀N₅O₁₀P
• 分子量: 861.973
• InChiKey: FMISOXAPFLAVGZ-PXQFAMQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.34
• 重原子数：
  61.0
• 可旋转键数：
  17.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  221.32
• 氢给体数：
  5.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  N-[(S)-2-{1-[(S)-2-Carbamoyl-1-(3-naphthalen-1-yl-propylcarbamoyl)-ethylcarbamoyl]-cyclohexylcarbamoyl}-6-(diethoxy-phosphoryl)-1,2,3,4-tetrahydro-naphthalen-2-yl]-oxalamic acid tert-butyl ester 在 碘代三甲硅烷 、 茴香硫醚 、 三氟乙酸 作用下， 以 乙腈 为溶剂， 以74%的产率得到N-((S)-2-{1-[(S)-2-Carbamoyl-1-(3-naphthalen-1-yl-propylcarbamoyl)-ethylcarbamoyl]-cyclohexylcarbamoyl}-6-phosphono-1,2,3,4-tetrahydro-naphthalen-2-yl)-oxalamic acid
  参考文献：
  名称：

  Synthesis of α,α-disubstituted 4-phosphonophenylalanine analogues as conformationally-constrained phosphotyrosyl mimetics

  摘要：

  Syntheses of N-Boc (S)-4-(diethylphosphono)-(alpha-methyl)phenylalanine [Boc-(alpha-Me)Phe(4-PO3Et2)-OH] (9) and N-Boc (S)-2amino-6-(diethylphosphono)tetralin-2-carboxylic acid [Boc-Atc(6-PO3Et2)-OH] (18) are reported as conformationally-constrained phosphotyrosyl mimetics suitably protected for peptide synthesis. Both syntheses proceeded through chiral arylhalides that are converted to arylphosphonates by palladium-catalyzed cross coupling with diethylphosphite. These amino acid analogues may be useful in the study of cellular signal transduction processes. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.02.005
• 作为产物：
  描述：

  6-溴-2-四氢萘酮 在 palladium on activated charcoal barium dihydroxide 、 lithium hydroxide 、 四(三苯基膦)钯 、 氯化亚砜 、 (S)-(+)-扁桃酸 、 氢气 、 碳酸氢铵 、 苯甲醚 、 三乙胺 、 N,N-二异丙基乙胺 、 fluoro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙醇 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 112.0h， 生成 N-[(S)-2-{1-[(S)-2-Carbamoyl-1-(3-naphthalen-1-yl-propylcarbamoyl)-ethylcarbamoyl]-cyclohexylcarbamoyl}-6-(diethoxy-phosphoryl)-1,2,3,4-tetrahydro-naphthalen-2-yl]-oxalamic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of α,α-disubstituted 4-phosphonophenylalanine analogues as conformationally-constrained phosphotyrosyl mimetics

  摘要：

  Syntheses of N-Boc (S)-4-(diethylphosphono)-(alpha-methyl)phenylalanine [Boc-(alpha-Me)Phe(4-PO3Et2)-OH] (9) and N-Boc (S)-2amino-6-(diethylphosphono)tetralin-2-carboxylic acid [Boc-Atc(6-PO3Et2)-OH] (18) are reported as conformationally-constrained phosphotyrosyl mimetics suitably protected for peptide synthesis. Both syntheses proceeded through chiral arylhalides that are converted to arylphosphonates by palladium-catalyzed cross coupling with diethylphosphite. These amino acid analogues may be useful in the study of cellular signal transduction processes. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.02.005