Cbz(L)-phenylalanine-phthalimide | 827624-64-6

• 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: Cbz(L)-phenylalanine-phthalimide
• 英文别名: benzyl N-[(2S)-1-[(1,3-dioxoisoindol-2-yl)amino]-1-oxo-3-phenylpropan-2-yl]carbamate
• CAS: 827624-64-6
• 化学式: C₂₅H₂₁N₃O₅
• 分子量: 443.459
• InChiKey: HACLKVXUCDBVLJ-NRFANRHFSA-N

物化性质

• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Cbz(L)-phenylalanine-phthalimide 在 aminomethyl polystyrene resin 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以88%的产率得到N-benzyloxycarbonyl-L-phenylalanine hydrazide
  参考文献：
  名称：

  Enantioselective Synthesis of N-Protected α-Amino Acid Hydrazides

  摘要：

  描述了一种新的、温和的、通用的且高效的N-保护α-氨基酸酰肼合成方法。该两步法利用N-氨基酞菁作为保护性酰肼制备N-保护α-氨基酸酰肼前体，随后通过氨基甲基聚苯乙烯树脂的去酞菁化反应得到N-保护α-氨基酸酰肼。其优点在于避免了使用有毒的酰肼试剂，并与最常用的N-保护基团相容。对于N-(9-芴基甲氧羰基)保护的氨基酸而言，该策略尤为有趣。在手性HPLC检测的限制范围内，未观察到外消旋化现象。

  DOI：

  10.1055/s-0028-1088013
• 作为产物：
  描述：

  N-(苄氧羰基)-L-苯丙氨酸甲酯 在 一水合肼 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 18.0h， 生成 Cbz(L)-phenylalanine-phthalimide
  参考文献：
  名称：

  A family of strong low-molecular-weight organogelators based on aminoacid derivatives

  摘要：

  A new family of potent aminoacid-type organogelators obtained via an easy and unexpensive way is described. We demonstrated that structural variations onto the side chains of the aminoacid derivatives allowed modulations of the gelation properties. The organogelators bearing a benzyl or an isopropyl group (compounds 1e, 2a, and 2c) are able to provide gelation of apolar solvents at very low concentration ( less than or equal to 0.2 wt%) and to form thermostable gels. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.10.139

文献信息

• Oligomerization of N-aminodipeptides: to the synthesis of heterogeneous backbone with 1:1 α:α-N-amino aminoacid residue patterns
  作者：Anne-Sophie Felten、Sébastien Dautrey、Jacques Bodiguel、Régis Vanderesse、Claude Didierjean、Axelle Arrault、Brigitte Jamart-Grégoire

  DOI：10.1016/j.tet.2008.08.087

  日期：2008.11

  A large number of N-aminodipeptides compounds have been obtained via a Mitsunobu protocol performed in Solution or by solid-phase synthesis. The oligomerization of some of them has been studied in solution or on solid support leading to the formation of 1:1[alpha:alpha-N-amino]mers. (C) 2008 Elsevier Ltd. All rights reserved.
• Enantioselective Synthesis of N-Protected α-Amino Acid Hydrazides
  作者：Jean-Alain Fehrentz、Mathieu Bibian、Sarah El-Habnouni、Jean Martinez

  DOI：10.1055/s-0028-1088013

  日期：2009.4

  A new, mild, general, and efficient synthesis of N-protected α-amino acid hydrazides is described. This two-step preparation uses N-aminophthalimide as protected hydrazine to prepare N-protected α-amino acid hydrazide precursors, and subsequent de­phthaloylation with an aminomethyl polystyrene resin yields N-protected α-amino acid hydrazides. It has the advantages of avoiding the use of the toxic hydrazine reagent and being compatible with the most commonly used N-protecting groups. This strategy is particularly interesting in the case of N-(9-fluorenylmethoxycarbonyl)-protected amino acids. Within the limits of chiral HPLC detection, no epimerization is apparent.

  描述了一种新的、温和的、通用的且高效的N-保护α-氨基酸酰肼合成方法。该两步法利用N-氨基酞菁作为保护性酰肼制备N-保护α-氨基酸酰肼前体，随后通过氨基甲基聚苯乙烯树脂的去酞菁化反应得到N-保护α-氨基酸酰肼。其优点在于避免了使用有毒的酰肼试剂，并与最常用的N-保护基团相容。对于N-(9-芴基甲氧羰基)保护的氨基酸而言，该策略尤为有趣。在手性HPLC检测的限制范围内，未观察到外消旋化现象。
• A family of strong low-molecular-weight organogelators based on aminoacid derivatives
  作者：Nicolas Brosse、Danielle Barth、Brigitte Jamart-Grégoire

  DOI：10.1016/j.tetlet.2004.10.139

  日期：2004.12

  A new family of potent aminoacid-type organogelators obtained via an easy and unexpensive way is described. We demonstrated that structural variations onto the side chains of the aminoacid derivatives allowed modulations of the gelation properties. The organogelators bearing a benzyl or an isopropyl group (compounds 1e, 2a, and 2c) are able to provide gelation of apolar solvents at very low concentration ( less than or equal to 0.2 wt%) and to form thermostable gels. (C) 2004 Elsevier Ltd. All rights reserved.