N'-(6-aminohexyl)-N-tert-Boc-L-phenylalaninamide | 446878-27-9

• 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: N'-(6-aminohexyl)-N-tert-Boc-L-phenylalaninamide
• 英文别名: tert-butyl-N-[(S)-1-(6-aminohexylcarbamoyl)-2-phenylethyl]carbamate；tert-butyl N-[(2S)-1-(6-aminohexylamino)-1-oxo-3-phenylpropan-2-yl]carbamate
• CAS: 446878-27-9
• 化学式: C₂₀H₃₃N₃O₃
• 分子量: 363.5
• InChiKey: KVLSJQSEJRPIIE-KRWDZBQOSA-N

物化性质

• 沸点：
  574.5±50.0 °C(Predicted)
• 密度：
  1.060±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  26
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  93.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N'-(6-aminohexyl)-N-tert-Boc-L-phenylalaninamide 在 palladium on activated charcoal 氢气 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 5.0h， 生成 N'-(6-(carboxymethyl-1,3-ureido)hexyl)-N-tert-Boc-L-phenylalaninamide
  参考文献：
  名称：

  The chirality of dendrimer-based supramolecular complexes

  摘要：

  Boc保护的L-苯丙氨酸已与一个间隔臂的尿素–乙酸衍生物连接，该衍生物可以在氯仿中与尿素–阿达曼蒂尔修饰的聚（丙烯亚胺）树状聚合物形成多个超分子复合物。制备了该客体与几代尿素–阿达曼蒂尔树状聚合物的复合物。通过1H-NMR、1H–1H-NOESY光谱和质谱详细表征了树状聚合物–客体复合物，以证明其形成。在不同代数的树状聚合物–客体复合物上进行的光学旋转实验显示出恒定的正值。这些观察表明，尽管客体分子在结合时减少了树状聚合物周边的柔韧性，但客体分子末端的氨基酸仍然保持较高的局部构象自由度。这与对共价修饰的间隔臂树状聚合物所发现的数值相一致。

  DOI：

  10.1039/b413724h
• 作为产物：
  描述：

  9H-fluoren-9-ylmethyl N-(6-aminohexyl)carbamate 在 哌啶 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N'-(6-aminohexyl)-N-tert-Boc-L-phenylalaninamide
  参考文献：
  名称：

  New series of potent δ-opioid antagonists containing the H-Dmt-Tic-NH-hexyl-NH-R motif

  摘要：

  Heterodimeric compounds H-Dmt-Tic-NH-hexyl-NH-R (R = Dmt, Tic, and Phe) exhibited high affinity to delta-(K-i delta = 0.13-0.89 nM) and p-opioid receptors (K-i mu = 0.38-2.81 nM) with extraordinary potent delta antagonism (pA(2) = 10.2-10.4). These compounds represent the prototype for a new class of structural homologues lacking mu-opioid receptor-associated agonism IC50 = 1.6-5.8 mu M) based on the framework of bis-[H-Dmt-NH]-alkyl (Okada, Y.; Tsuda, Y.; Fujita, Y.; YDkoi, T.; Sasaki, Y.; Ambo, A.; Konishi, R.; Nagata, M.; Salvadori, S.; Jinsmaa, Y.; Bryant, S. D.; Lazarus, L. H. J. Med. Chem. 2003, 46, 3201), which exhibited both high p affinity and bioactivity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.08.073

文献信息

• Efficient monoacylation of symmetrical secondary alkanediamines and synthesis of unsymmetrical diacylated alkanediamines. A new L-proline-based organocatalyst
  作者：Laure Moulat、Jean Martinez、Xavier J. Salom-Roig

  DOI：10.24820/ark.5550190.p011.054

  日期：——

  developed for the monoacylation of several unprotected alkanediamines with carboxylic acids by using PyBOP-HOBt as coupling agent in the presence of DIEA at room temperature. Yields were moderate with primary alkanediamines and good to excellent with linear or cyclic secondary ones. To illustrate the utility of these monoacylated products, six unsymmetrical diacylated alkanediamines were synthesized

  通过使用 PyBOP-HOBt 作为偶联剂，在室温下，在 DIEA 的存在下，开发了一种简单的程序，用于将几种未保护的链烷二胺与羧酸进行单酰化。伯链烷二胺的产率适中，直链或环状仲胺的产率从好到极好。为了说明这些单酰化产物的效用，合成了六种不对称的二酰化链烷二胺。此外，这些化合物之一被评估为不对称羟醛反应中的有机催化剂。
• The chirality of dendrimer-based supramolecular complexes
  作者：Maarten A. C. Broeren、Bas F. M. de Waal、Joost L. J. van Dongen、Marcel H. P. van Genderen、E. W. Meijer

  DOI：10.1039/b413724h

  日期：——

  Boc-protected L-phenylalanine has been connected to a spacer-armed ureido–acetic acid derivative, which can form multiple supramolecular complexes with urea–adamantyl modified poly(propylene imine) dendrimers in chloroform. Complexes of this guest with several generations of urea–adamantyl dendrimers were prepared. The dendrimer–guest complexes were characterized in detail by 1H-NMR, 1H–1H-NOESY spectroscopy and mass spectrometry to prove their formation. Optical rotation experiments performed on different generations of dendrimer–guest complexes showed a constant positive value. These observations indicate that, though guest molecules decrease the flexibility at the periphery of the dendrimer upon binding, the amino acid at the terminus of the guest molecule retains its high local conformational freedom. This is in agreement with values found for covalently modified spacer-armed dendrimers.

  Boc保护的L-苯丙氨酸已与一个间隔臂的尿素–乙酸衍生物连接，该衍生物可以在氯仿中与尿素–阿达曼蒂尔修饰的聚（丙烯亚胺）树状聚合物形成多个超分子复合物。制备了该客体与几代尿素–阿达曼蒂尔树状聚合物的复合物。通过1H-NMR、1H–1H-NOESY光谱和质谱详细表征了树状聚合物–客体复合物，以证明其形成。在不同代数的树状聚合物–客体复合物上进行的光学旋转实验显示出恒定的正值。这些观察表明，尽管客体分子在结合时减少了树状聚合物周边的柔韧性，但客体分子末端的氨基酸仍然保持较高的局部构象自由度。这与对共价修饰的间隔臂树状聚合物所发现的数值相一致。
• New series of potent δ-opioid antagonists containing the H-Dmt-Tic-NH-hexyl-NH-R motif
  作者：Tingyou Li、Kimitaka Shiotani、Anna Miyazaki、Yoshio Fujita、Yuko Tsuda、Akihiro Ambo、Yusuke Sasaki、Yunden Jinsmaa、Ewa Marczak、Sharon D. Bryant、Lawrence H. Lazarus、Yoshio Okada

  DOI：10.1016/j.bmcl.2005.08.073

  日期：2005.12

  Heterodimeric compounds H-Dmt-Tic-NH-hexyl-NH-R (R = Dmt, Tic, and Phe) exhibited high affinity to delta-(K-i delta = 0.13-0.89 nM) and p-opioid receptors (K-i mu = 0.38-2.81 nM) with extraordinary potent delta antagonism (pA(2) = 10.2-10.4). These compounds represent the prototype for a new class of structural homologues lacking mu-opioid receptor-associated agonism IC50 = 1.6-5.8 mu M) based on the framework of bis-[H-Dmt-NH]-alkyl (Okada, Y.; Tsuda, Y.; Fujita, Y.; YDkoi, T.; Sasaki, Y.; Ambo, A.; Konishi, R.; Nagata, M.; Salvadori, S.; Jinsmaa, Y.; Bryant, S. D.; Lazarus, L. H. J. Med. Chem. 2003, 46, 3201), which exhibited both high p affinity and bioactivity. (c) 2005 Elsevier Ltd. All rights reserved.