(S)-3-tert-butoxycarbonylamino-4-phenylbutanamide | 312311-58-3

• 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)-3-tert-butoxycarbonylamino-4-phenylbutanamide
• 英文别名: (S)-Boc-β-Phe-NH2；tert-butyl N-[(2S)-4-amino-4-oxo-1-phenylbutan-2-yl]carbamate
• CAS: 312311-58-3
• 化学式: C₁₅H₂₂N₂O₃
• 分子量: 278.351
• InChiKey: WOJVROVWMFJAEM-LBPRGKRZSA-N

物化性质

• 熔点：
  128-131 °C
• 沸点：
  493.5±45.0 °C(Predicted)
• 密度：
  1.107±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  81.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-3-tert-butoxycarbonylamino-4-phenylbutanamide 在 lithium hydroxide 、 水 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 27.0h， 生成 (S)-3-(Boc-氨基)-4-苯基丁酸
  参考文献：
  名称：

  Pseudoaxially Disubstituted Cyclo-β3-tetrapeptide Scaffolds

  摘要：

  An N,N-disubstituted cyclo-beta(3)-tetrapeptide, identified as a potential molecular scaffold, has been synthesised on a multigram scale from beta-homophenylalanine by employing a nosylate-based protection strategy. C-2-Symmetric derivatives containing pseudoaxial, combinatorially addressable functionalities have been prepared from the parent cyclopeptide. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00666-9
• 作为产物：
  描述：

  ethoxycarbonyl (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoate 在 TEA 、 氨 、 silver trifluoroacetate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 (S)-3-tert-butoxycarbonylamino-4-phenylbutanamide
  参考文献：
  名称：

  Endomorphin-1 Analogues Containing β-Proline Are μ-Opioid Receptor Agonists and Display Enhanced Enzymatic Hydrolysis Resistance

  摘要：

  In this paper we describe the synthesis and affinity toward the mu-opioid receptor of some tetrapeptides obtained from endomorphin-1, H-Tyr-Pro-Trp-Phe-NH2 (1), by substituting each amino acid in turn with its homologue. The ability to bind p-opioid receptors depends on the beta-amino acid, and in particular 4, which contains beta-L-Pro, has a K-1 in the nanomolar range. The peptides 4 and 5 are significantly more resistant to enzymatic hydrolysis than 1. The same compounds, as well as they-opioid receptor agonist DAMGO, produced a concentration-dependent inhibition of forskolin-stimulated cyclic AMP formation, thus behaving as mu-opioid agonists. These features suggest that this novel class of endomorphin-1 analogues may represent suitable candidates for the in vivo investigation as potential mu-opioid receptor agonists.

  DOI：

  10.1021/jm011059z

文献信息

• Lipase-Involved Strategy to the Enantiomers of 4-Benzyl-β-Lactam as a Key Intermediate in the Preparation of β-Phenylalanine Derivatives
  作者：Xiang-Guo Li、Liisa T. Kanerva

  DOI：10.1002/adsc.200505253

  日期：2006.1

  A simple chemoenzymatic method for the preparation of the enantiomers of 4-benzyl-β-lactam (4-benzylazetidin-2-one) from allylbenzene has been described. The enantiomers of this key intermediate have been used to produce the corresponding enantiomers of β-phenylalanine and N-Boc-protected β-phenylalanine amide through the simple cleavage of the lactam ring by acid-catalyzed hydrolysis and by ammonolysis

  已经描述了一种从烯丙基苯制备4-苄基-β-内酰胺（4-苄基氮杂环丁烷-2-酮）对映异构体的简单化学酶促方法。该关键中间体的对映异构体已通过分别通过酸催化水解和通过氨解简单地裂解内酰胺环而用于生产相应的β-苯丙氨酸和N -Boc保护的β-苯丙氨酸酰胺的对映异构体。Burkholderia cepacia脂肪酶催化的动力学双分辨技术负责实现产品中的对映体纯度。这是通过酰化进行Ñ -hydroxymethylatedβ内酰胺，随后所得到的（的butanolysis小号）-酯。还研究了直接脂肪酶催化的β-内酰胺环的裂解。
• Endomorphin-1 Analogues Containing β-Proline Are μ-Opioid Receptor Agonists and Display Enhanced Enzymatic Hydrolysis Resistance
  作者：Giuliana Cardillo、Luca Gentilucci、Ahmed R. Qasem、Fabio Sgarzi、Santi Spampinato

  DOI：10.1021/jm011059z

  日期：2002.6.1

  In this paper we describe the synthesis and affinity toward the mu-opioid receptor of some tetrapeptides obtained from endomorphin-1, H-Tyr-Pro-Trp-Phe-NH2 (1), by substituting each amino acid in turn with its homologue. The ability to bind p-opioid receptors depends on the beta-amino acid, and in particular 4, which contains beta-L-Pro, has a K-1 in the nanomolar range. The peptides 4 and 5 are significantly more resistant to enzymatic hydrolysis than 1. The same compounds, as well as they-opioid receptor agonist DAMGO, produced a concentration-dependent inhibition of forskolin-stimulated cyclic AMP formation, thus behaving as mu-opioid agonists. These features suggest that this novel class of endomorphin-1 analogues may represent suitable candidates for the in vivo investigation as potential mu-opioid receptor agonists.
• Pseudoaxially Disubstituted Cyclo-β3-tetrapeptide Scaffolds
  作者：P Sutton

  DOI：10.1016/s0040-4020(00)00666-9

  日期：2000.9.29

  An N,N-disubstituted cyclo-beta(3)-tetrapeptide, identified as a potential molecular scaffold, has been synthesised on a multigram scale from beta-homophenylalanine by employing a nosylate-based protection strategy. C-2-Symmetric derivatives containing pseudoaxial, combinatorially addressable functionalities have been prepared from the parent cyclopeptide. (C) 2000 Elsevier Science Ltd. All rights reserved.