benzyl (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-phenylpentanoate | 216753-81-0

• 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: benzyl (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-phenylpentanoate
• CAS: 216753-81-0
• 化学式: C₂₃H₂₉NO₄
• 分子量: 383.488
• InChiKey: QCVXCFAUAFJUFN-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 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：

  benzyl (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-phenylpentanoate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (S)-2-Amino-5-phenyl-pentanoic acid benzyl ester
  参考文献：
  名称：

  Concise Synthesis of Enantiomerically Pure Phenylalanine, Homophenylalanine, and Bishomophenylalanine Derivatives Using Organozinc Chemistry:  NMR Studies of Amino Acid-Derived Organozinc Reagents

  摘要：

  Protected phenylalanines 23 (seven examples), homophenylalanines 7 (eight examples), and bishomophenylalanines 8 (seven examples) have been prepared by palladium-catalyzed coupling of the amino acid-derived organozinc reagents 13, 5, and 6, respectively, with aryl iodides. While the reactions of the zinc reagent 13 may be conducted in both THF and DMF as solvent, the results obtained in DMF are generally superior. In the case of the reagents 5 and 6 the results are far superior in DMF. NMR investigations on the structure of the zinc reagents 13 in THF suggest that there is strong intramolecular coordination of the urethane carbonyl group, whereas in DMF this interaction is completely suppressed.

  DOI：

  10.1021/jo981133u
• 作为产物：
  描述：

  benzyl (S)-2-((tert-butoxycarbonyl)amino)-5-hydroxypentanoate 在 咪唑 、 三甲基氯硅烷 、 tris(dibenzylideneacetone)dipalladium (0) 、 碘 、 1,2-二溴乙烷 、 三苯基膦 、 三(邻甲基苯基)磷 、 锌 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 生成 benzyl (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-phenylpentanoate
  参考文献：
  名称：

  Concise Synthesis of Enantiomerically Pure Phenylalanine, Homophenylalanine, and Bishomophenylalanine Derivatives Using Organozinc Chemistry:  NMR Studies of Amino Acid-Derived Organozinc Reagents

  摘要：

  Protected phenylalanines 23 (seven examples), homophenylalanines 7 (eight examples), and bishomophenylalanines 8 (seven examples) have been prepared by palladium-catalyzed coupling of the amino acid-derived organozinc reagents 13, 5, and 6, respectively, with aryl iodides. While the reactions of the zinc reagent 13 may be conducted in both THF and DMF as solvent, the results obtained in DMF are generally superior. In the case of the reagents 5 and 6 the results are far superior in DMF. NMR investigations on the structure of the zinc reagents 13 in THF suggest that there is strong intramolecular coordination of the urethane carbonyl group, whereas in DMF this interaction is completely suppressed.

  DOI：

  10.1021/jo981133u

文献信息

• Concise Synthesis of Enantiomerically Pure Phenylalanine, Homophenylalanine, and Bishomophenylalanine Derivatives Using Organozinc Chemistry:  NMR Studies of Amino Acid-Derived Organozinc Reagents
  作者：Richard F. W. Jackson、Rebecca J. Moore、Charles S. Dexter、Jason Elliott、Charles E. Mowbray

  DOI：10.1021/jo981133u

  日期：1998.10.1

  Protected phenylalanines 23 (seven examples), homophenylalanines 7 (eight examples), and bishomophenylalanines 8 (seven examples) have been prepared by palladium-catalyzed coupling of the amino acid-derived organozinc reagents 13, 5, and 6, respectively, with aryl iodides. While the reactions of the zinc reagent 13 may be conducted in both THF and DMF as solvent, the results obtained in DMF are generally superior. In the case of the reagents 5 and 6 the results are far superior in DMF. NMR investigations on the structure of the zinc reagents 13 in THF suggest that there is strong intramolecular coordination of the urethane carbonyl group, whereas in DMF this interaction is completely suppressed.