(S)-N-(tert-Butyl)-N^α-phthaloylphenylalaninamide | 135395-13-0

• 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: (S)-N-(tert-Butyl)-N^α-phthaloylphenylalaninamide
• 英文别名: L-N-tert-butyl-N²-phthaloylphenylalanylamide；(2S)-N-tert-butyl-2-(1,3-dioxoisoindol-2-yl)-3-phenylpropanamide
• CAS: 135395-13-0
• 化学式: C₂₁H₂₂N₂O₃
• mdl: MFCD00371933
• 分子量: 350.417
• InChiKey: ZXOMINDCJKYFOL-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  66.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-N-(tert-Butyl)-N^α-phthaloylphenylalaninamide 在 盐酸 、 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 碳酸氢钠 、 一水合肼 、 silver(l) oxide 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 20.5h， 生成 (2S,3R)-N-(tert-butyloxycarbonyl)-3-methoxyphenylalanine methyl ester
  参考文献：
  名称：

  Total Synthesis of Cyclomarin C

  摘要：

  The total synthesis of cyclomarin C was accomplished through a convergent strategy from a tetrapeptide fragment and a tripeptide one. The developed methods to prepare the needed noncoded amino acids, the proper protection of peptide fragments, and identification of the optimum macrocylization site can be applied to further synthetic studies on other members of cyclomarins.

  DOI：

  10.1021/ol049065n
• 作为产物：
  描述：

  N-tert-Butyl-N^α-phthaloyl-β-bromophenylalaninamide 在 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 4.0h， 以88%的产率得到(S)-N-(tert-Butyl)-N^α-phthaloylphenylalaninamide
  参考文献：
  名称：

  Regioselective functionalization of N-phthaloyl-substituted amino acid and peptide derivatives

  摘要：

  The free-radical reactions of a range of amino acid derivatives with N-bromosuccinimide are described. The products and relative rates of these reactions indicate that the alpha-position of an N-phthaloyl-substituted alpha-amino acid derivative is much less reactive than that of a corresponding N-acyl amino acid derivative toward hydrogen atom transfer. This is attributed to the proactive effects of acylamino and carboxyl substituents, in contrast to the counteractive effects of phthalimido and carboxyl groups. The reactions exemplify procedures for the regiocontrolled functionalization of amino acid and peptide derivatives.

  DOI：

  10.1021/jo00019a029

文献信息

• Stereocontrolled synthesis of β-hydroxyphenylalanine and β-hydroxytyrosine derivatives
  作者：Christopher J. Easton、Craig A. Hutton、Peter D. Roselt、Edward R.T. Tiekink

  DOI：10.1016/s0040-4020(01)85256-x

  日期：1994.1

  Side-chain bromination of N-phthaloyl-(S)-phenylalanine and tyrosine derivatives, followed by treatment of the product bromides with silver nitrate in aqueous acetone, affords the corresponding (2S,3R)-beta-hydroxy-alpha-amino acids, enantiospecifically and diastereoselectively. The diastereoselectivity depends on the carboxyl protecting group, tert-Butyl esters display greater stereoselectivity than the corresponding methyl esters, presumably as a result of a steric effect, while N-tert-butylamides react diastereospecifically due to a combination of steric and electronic effects.
• EASTON, CHRISTOPHER J.;HUTTON, CRAIG A.;ROSELT, PETER D.;TIEKINK, EDWARD +, AUSTRAL. J. CHEM., 44,(1991) N, C. 687-694
  作者：EASTON, CHRISTOPHER J.、HUTTON, CRAIG A.、ROSELT, PETER D.、TIEKINK, EDWARD +

  DOI：——

  日期：——
• Total Synthesis of Cyclomarin C
  作者：Shi-Jun Wen、Zhu-Jun Yao

  DOI：10.1021/ol049065n

  日期：2004.8.1

  The total synthesis of cyclomarin C was accomplished through a convergent strategy from a tetrapeptide fragment and a tripeptide one. The developed methods to prepare the needed noncoded amino acids, the proper protection of peptide fragments, and identification of the optimum macrocylization site can be applied to further synthetic studies on other members of cyclomarins.
• Regioselective functionalization of N-phthaloyl-substituted amino acid and peptide derivatives
  作者：Christopher J. Easton、Craig A. Hutton、Giovanna Rositano、Eng Wui Tan

  DOI：10.1021/jo00019a029

  日期：1991.9

  The free-radical reactions of a range of amino acid derivatives with N-bromosuccinimide are described. The products and relative rates of these reactions indicate that the alpha-position of an N-phthaloyl-substituted alpha-amino acid derivative is much less reactive than that of a corresponding N-acyl amino acid derivative toward hydrogen atom transfer. This is attributed to the proactive effects of acylamino and carboxyl substituents, in contrast to the counteractive effects of phthalimido and carboxyl groups. The reactions exemplify procedures for the regiocontrolled functionalization of amino acid and peptide derivatives.