methyl (S)-2-(tert-butyloxycarbonyl)amino-1,2,3,4-tetrahydro-6-bromo-2-naphthalenecarboxylate | 690254-47-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl (S)-2-(tert-butyloxycarbonyl)amino-1,2,3,4-tetrahydro-6-bromo-2-naphthalenecarboxylate
• 英文别名: methyl (2S)-6-bromo-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3,4-dihydro-1H-naphthalene-2-carboxylate
• CAS: 690254-47-8
• 化学式: C₁₇H₂₂BrNO₄
• 分子量: 384.27
• InChiKey: BGONHTKULWEQLV-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (S)-2-(tert-butyloxycarbonyl)amino-1,2,3,4-tetrahydro-6-bromo-2-naphthalenecarboxylate 在 palladium on activated charcoal lithium hydroxide 、 四(三苯基膦)钯 、 碘代三甲硅烷 、 茴香硫醚 、 氢气 、 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 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 24.0h， 生成 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 barium dihydroxide 、 氯化亚砜 、 (S)-(+)-扁桃酸 、 碳酸氢铵 作用下， 以 甲醇 、 乙醚 、 乙醇 、 水 为溶剂， 反应 88.0h， 生成 methyl (S)-2-(tert-butyloxycarbonyl)amino-1,2,3,4-tetrahydro-6-bromo-2-naphthalenecarboxylate
  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

文献信息

• Examination of Acylated 4-Aminopiperidine-4-carboxylic Acid Residues in the Phosphotyrosyl+1 Position of Grb2 SH2 Domain-Binding Tripeptides
  作者：Sang-Uk Kang、Won Jun Choi、Shinya Oishi、Kyeong Lee、Rajeshri G. Karki、Karen M. Worthy、Lakshman K. Bindu、Marc C. Nicklaus、Robert J. Fisher、Terrence R. Burke

  DOI：10.1021/jm0614073

  日期：2007.4.1

  A 4-aminopiperidine-4-carboxylic acid residue was placed in the pTyr+1 position of a Grb2 SH2 domain-binding peptide to form a general platform, which was then acylated with a variety of groups to yield a library of compounds designed to explore potential binding interactions, with protein features lying below the beta D strand. The highest affinities were obtained using phenylethyl carbamate and phenylbutyrylamide functionalities.
• Synthesis of α,α-disubstituted 4-phosphonophenylalanine analogues as conformationally-constrained phosphotyrosyl mimetics
  作者：Shinya Oishi、Sang-Uk Kang、Hongpeng Liu、Manchao Zhang、Dajun Yang、Jeffrey R. Deschamps、Terrence R. Burke

  DOI：10.1016/j.tet.2004.02.005

  日期：2004.3

  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.