(S)-2-amino-4-methyl-N-propylpentanamide

• 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)-2-amino-4-methyl-N-propylpentanamide
• 英文别名: l-Leucin-propylamid；Leucine n-propylamide；(2S)-2-amino-4-methyl-N-propylpentanamide
• 化学式: C₉H₂₀N₂O
• 分子量: 172.271
• InChiKey: AOCMGSAEDNRBKZ-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-2-amino-4-methyl-N-propylpentanamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.81h， 生成 (S)-4-methyl-N₁-propylpentane-1,2-diamine
  参考文献：
  名称：

  通过使用新型的伯-仲二胺催化剂，将丙二酸酯有机催化的高对映选择性的丙二酸迈克尔加成反应。

  摘要：

  DOI：

  10.1002/chem.200801749
• 作为产物：
  描述：

  tert-butyl N-[(S)-3-methyl-1-(propylcarbamoyl)butyl]carbamate 在 三氟乙酸 、 水 、 sodium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (S)-2-amino-4-methyl-N-propylpentanamide
  参考文献：
  名称：

  The urea-dipeptides show stronger H-bonding propensity to nucleate β-sheetlike assembly than natural sequence

  摘要：

  In this article, we report the distinct solution behavior of a set of urea-dipeptides to that of natural sequence. The urea-dipeptides adopt beta-folding conformations and form into beta-sheetlike assembly in chloroform. Most surprisedly, the urea-dipeptides tend to form interpeptide H-bonding interactions even at a concentration of as low as 0 1 mM, while the natural sequence shows H-bonding propensity at a concentration of about 7 mM, indicating that the urea-dipeptides Show Much stronger H-bonding propensity to nucleate formation of beta-sheetlike assembly than the natural sequence CD spectra reveal that the investigated urea-dipeptides have two negative CD bands, respectively, around 217 nm and 224 nm, supporting the beta-folding conformations and in turn formation of beta-sheetlike assembly. The beta-sheetlike assembly is also confirmed by the XRD reflections, which give two typical d-spacings of 12 7 and 4 8 angstrom, respectively, corresponding to stacking periodicity of the beta-sheets and the spacing between peptide backbones running orthogonal to the beta-sheet axis. (C) 2009 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tet.2009.07.048

文献信息

• Direct amidation of unprotected amino acids using B(OCH₂CF₃)₃
  作者：Rachel M. Lanigan、Valerija Karaluka、Marco T. Sabatini、Pavel Starkov、Matthew Badland、Lee Boulton、Tom D. Sheppard

  DOI：10.1039/c6cc05147b

  日期：——

  A commercially available borate ester, B(OCH2CF3)3, can be used to achieve protecting-group free direct amidation of [small alpha]-amino acids with a range of amines in cyclopentyl methyl ether. The method can...

  可商购的硼酸酯B（OCH 2 CF 3）3可用于在环戊基甲基醚中实现小α-氨基酸与一系列胺的无保护基的直接酰胺化。该方法可以...
• Protecting-Group-Free Amidation of Amino Acids using Lewis Acid Catalysts
  作者：Marco T. Sabatini、Valerija Karaluka、Rachel M. Lanigan、Lee T. Boulton、Matthew Badland、Tom D. Sheppard

  DOI：10.1002/chem.201800372

  日期：2018.5.11

  Amidation of unprotected amino acids has been investigated using a variety of ‘classical“ coupling reagents, stoichiometric or catalytic group(IV) metal salts, and boron Lewis acids. The scope of the reaction was explored through the attempted synthesis of amides derived from twenty natural, and several unnatural, amino acids, as well as a wide selection of primary and secondary amines. The study also

  已使用多种“经典”偶联剂，化学计量或催化基团（IV）金属盐和硼路易斯酸研究了未保护氨基酸的酰胺化。通过尝试合成衍生自二十种天然和几种非天然氨基酸以及广泛选择的伯胺和仲胺的酰胺，探索了反应的范围。该研究还研究了药用相关化合物的合成，以及这种直接酰胺化方法的可扩展性。最后，我们提供了对在这些反应中观察到的化学选择性的见解。
• 1,2,4-Substituted 5(4H)-Imidazolones¹
  作者：Sara Ginsburg

  DOI：10.1021/jo01058a513

  日期：1962.11
• The urea-dipeptides show stronger H-bonding propensity to nucleate β-sheetlike assembly than natural sequence
  作者：Damei Ke、Chuanlang Zhan、Xiao Li、Alexander D.Q. Li、Jiannian Yao

  DOI：10.1016/j.tet.2009.07.048

  日期：2009.9

  In this article, we report the distinct solution behavior of a set of urea-dipeptides to that of natural sequence. The urea-dipeptides adopt beta-folding conformations and form into beta-sheetlike assembly in chloroform. Most surprisedly, the urea-dipeptides tend to form interpeptide H-bonding interactions even at a concentration of as low as 0 1 mM, while the natural sequence shows H-bonding propensity at a concentration of about 7 mM, indicating that the urea-dipeptides Show Much stronger H-bonding propensity to nucleate formation of beta-sheetlike assembly than the natural sequence CD spectra reveal that the investigated urea-dipeptides have two negative CD bands, respectively, around 217 nm and 224 nm, supporting the beta-folding conformations and in turn formation of beta-sheetlike assembly. The beta-sheetlike assembly is also confirmed by the XRD reflections, which give two typical d-spacings of 12 7 and 4 8 angstrom, respectively, corresponding to stacking periodicity of the beta-sheets and the spacing between peptide backbones running orthogonal to the beta-sheet axis. (C) 2009 Elsevier Ltd All rights reserved
• [EN] NOVEL 2,4,6-TRI-SUBSTITUTED HETEROCYCLES AND USES THEREOF<br/>[FR] NOUVEAUX HETEROCYCLES 2,4,6-TRISUBSTITUES ET UTILISATIONS DE CEUX-CI
  申请人：ASTRAZENECA AB

  公开号：WO2005003103A2

  公开（公告）日：2005-01-13

  Compounds of formula (I) and (II); their pharmaceutical compositions and methods of use for the treatment of neurological disorders related to amyloid ß protein production such as Alzheimer's disease.