(S)-2-(tert-butyloxycarbonyl)amino-1,2,3,4-tetrahydro-6-(diethylphosphono)-2-naphthalenecarboxylic acid benzyl ester | 690254-50-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-2-(tert-butyloxycarbonyl)amino-1,2,3,4-tetrahydro-6-(diethylphosphono)-2-naphthalenecarboxylic acid benzyl ester
• 英文别名: benzyl (2S)-6-diethoxyphosphoryl-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3,4-dihydro-1H-naphthalene-2-carboxylate
• CAS: 690254-50-3
• 化学式: C₂₇H₃₆NO₇P
• 分子量: 517.559
• InChiKey: DNZRLGPLYALUAA-MHZLTWQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S)-2-(tert-butyloxycarbonyl)amino-1,2,3,4-tetrahydro-6-(diethylphosphono)-2-naphthalenecarboxylic acid benzyl ester 在 palladium on activated charcoal 氢气 、 fluoro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 生成 ((S)-6-tert-Butoxycarbonylamino-6-{1-[(S)-2-carbamoyl-1-(3-naphthalen-1-yl-propylcarbamoyl)-ethylcarbamoyl]-cyclohexylcarbamoyl}-5,6,7,8-tetrahydro-naphthalen-2-yl)-phosphonic acid diethyl 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
• 作为产物：
  描述：

  6-溴-2-四氢萘酮 在 barium dihydroxide 、 lithium hydroxide 、 四(三苯基膦)钯 、 氯化亚砜 、 (S)-(+)-扁桃酸 、 碳酸氢铵 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙醇 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 112.0h， 生成 (S)-2-(tert-butyloxycarbonyl)amino-1,2,3,4-tetrahydro-6-(diethylphosphono)-2-naphthalenecarboxylic acid benzyl 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