tert-butyl N-[2-(2-anilinoethylamino)ethyl]carbamate | 174497-02-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: tert-butyl N-[2-(2-anilinoethylamino)ethyl]carbamate
• CAS: 174497-02-0
• 化学式: C₁₅H₂₅N₃O₂
• 分子量: 279.382
• InChiKey: MEMDJFQKOBLTMX-UHFFFAOYSA-N

物化性质

• 沸点：
  448.9±30.0 °C(Predicted)
• 密度：
  1.065±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  62.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[2-(2-anilinoethylamino)ethyl]carbamate 在 碳酸氢钠 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 0.33h， 生成
  参考文献：
  名称：

  人工β-片的固相合成

  摘要：

  本文描述了人工 β-折叠 1-4 的固相合成，它模拟了蛋白质 β-折叠的结构和氢键模式。在这些化合物中，分子模板在附着的肽链中诱导 β-折叠结构。模板由二脲和三脲衍生物组成，它们将肽链和拟肽链保持在附近，以及 β 链模拟物，它们与肽链形成氢键。合成包括在 Merrifield 树脂上构建“下”肽链，连接二脲或三脲模板的二胺或三胺部分，连接“上”肽和拟肽链，以及从树脂上切割所得的人工 β-折叠. 人工 β-折叠是通过 8-13 步从亮氨酸 Merrifield 中制备的，总产率为 33-67%。

  DOI：

  10.1021/ja9710971
• 作为产物：
  描述：

  N-叔丁氧羰基-2-氨基乙醛 、 N-苯基乙二胺 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以65%的产率得到tert-butyl N-[2-(2-anilinoethylamino)ethyl]carbamate
  参考文献：
  名称：

  Triurea Derivatives of Diethylenetriamine as Potential Templates for the Formation of Artificial β-Sheets¹

  摘要：

  This paper describes synthetic and structural studies of triurea derivatives of an N,N ''-disubstituted diethylenetriamine. Diethylenetriamine triureas 1 (PhN(CONHR(1))CH2CH2N(CONHR(2))CH2CH2N(CONHR(3))CH2CH2CN; 2a, R(1) = R(2) = R(3) = Ph; 2b, R(1) = R(2) = R(3) = CH3; 2c, R(1) = (S)-CH(CH(2)Ph)CO2CH3 R(2) = (S)-CH(i-Pr)CO2CH3, R(3) = (S)-CH((S)-s-Bu)CO2CH3)) are efficiently prepared in five or six steps from N-phenylethylenediamine. Infrared spectroscopy, H-1 NMR spectroscopy, and X-ray crystallography indicate that triureas 1 adopt intramolecularly hydrogen-bonded conformations, both in chloroform solution and in the solid state. The three urea groups form a hydrogen-bonded network: The carbonyl group of urea NCONHR(1) is hydrogen bonded to the NH group of urea NCONHR(2), and the carbonyl group of urea NCONHR(2) is hydrogen bonded to the NH group of urea NCONHR(3). The three R groups are aligned along the triurea backbone, pointing in roughly the same direction, like three fingers on a hand. Molecular modeling suggests that the triurea backbone will be a suitable template for the creation of artificial beta-sheets. When molecular mechanics energy minimization calculations are performed upon a triurea bearing three N-terminally linked peptide strands, a parallel beta-sheet is formed.

  DOI：

  10.1021/ja9536072

文献信息

• Three-stranded mixed artificial β-sheets
  作者：James S Nowick、Eric M Smith、Joseph W Ziller、A.J Shaka

  DOI：10.1016/s0040-4020(01)01092-4

  日期：2002.1

  of compounds, comprising molecular templates and attached peptide strands, that mimic a small three-stranded mixed β-sheet (6a and b). Each of these artificial β-sheets is composed of two different molecular templates and two dipeptide strands. One of the templates is based on a 5-amino-2-methoxybenzoic hydrazide group that mimics the hydrogen-bonding functionality of a peptide β-strand and serves as

  本文描述了模仿分子小三链混合β-折叠（6a和b）的一对化合物的设计，合成和结构评估，包括分子模板和连接的肽链）。这些人工β-折叠中的每一个均由两个不同的分子模板和两条二肽链组成。模板之一基于5-氨基-2-甲氧基苯甲酰肼基团，该基团模拟肽β链的氢键官能团并用作顶部链。该模板形成与中间肽链的反平行β-折叠相似的氢键模式。中间肽链形成类似于与底部肽链平行的β-折叠的氢键模式。另一个模板将三个链彼此相邻并基于三脲。在一个人工β-折叠片（6a）中，上脲基团和中脲基团以及中脲基团和下脲基团都通过二亚甲基（CH 2 CH 2）连锁店；在另一个（6b）中，上和中脲基团通过二亚甲基链连接，而中和下脲基团通过三亚甲基（CH 2 CH 2 CH 2）链连接。1 H NMR化学位移和NOE研究表明，这两种化合物均折叠形成CDCl 3溶液中的氢键合β-片状结构。化学位移研究表明，三链混合人工β-折叠片6比其较小的两
• Solid-Phase Synthesis of Artificial β-Sheets
  作者：Darren L. Holmes、Eric M. Smith、James S. Nowick

  DOI：10.1021/ja9710971

  日期：1997.8.1

  solid-phase syntheses of artificial β-sheets 1−4, which mimic the structure and hydrogen-bonding patterns of protein β-sheets. In these compounds, molecular templates induce β-sheet structures in attached peptide strands. The templates consist of di- and triurea derivatives, which hold peptide and peptidomimetic strands in proximity, and β-strand mimics, which hydrogen bond to the peptide strands. The syntheses

  本文描述了人工 β-折叠 1-4 的固相合成，它模拟了蛋白质 β-折叠的结构和氢键模式。在这些化合物中，分子模板在附着的肽链中诱导 β-折叠结构。模板由二脲和三脲衍生物组成，它们将肽链和拟肽链保持在附近，以及 β 链模拟物，它们与肽链形成氢键。合成包括在 Merrifield 树脂上构建“下”肽链，连接二脲或三脲模板的二胺或三胺部分，连接“上”肽和拟肽链，以及从树脂上切割所得的人工 β-折叠. 人工 β-折叠是通过 8-13 步从亮氨酸 Merrifield 中制备的，总产率为 33-67%。
• Triurea Derivatives of Diethylenetriamine as Potential Templates for the Formation of Artificial β-Sheets¹
  作者：James S. Nowick、Sami Mahrus、Eric M. Smith、Joseph W. Ziller

  DOI：10.1021/ja9536072

  日期：1996.1.1

  This paper describes synthetic and structural studies of triurea derivatives of an N,N ''-disubstituted diethylenetriamine. Diethylenetriamine triureas 1 (PhN(CONHR(1))CH2CH2N(CONHR(2))CH2CH2N(CONHR(3))CH2CH2CN; 2a, R(1) = R(2) = R(3) = Ph; 2b, R(1) = R(2) = R(3) = CH3; 2c, R(1) = (S)-CH(CH(2)Ph)CO2CH3 R(2) = (S)-CH(i-Pr)CO2CH3, R(3) = (S)-CH((S)-s-Bu)CO2CH3)) are efficiently prepared in five or six steps from N-phenylethylenediamine. Infrared spectroscopy, H-1 NMR spectroscopy, and X-ray crystallography indicate that triureas 1 adopt intramolecularly hydrogen-bonded conformations, both in chloroform solution and in the solid state. The three urea groups form a hydrogen-bonded network: The carbonyl group of urea NCONHR(1) is hydrogen bonded to the NH group of urea NCONHR(2), and the carbonyl group of urea NCONHR(2) is hydrogen bonded to the NH group of urea NCONHR(3). The three R groups are aligned along the triurea backbone, pointing in roughly the same direction, like three fingers on a hand. Molecular modeling suggests that the triurea backbone will be a suitable template for the creation of artificial beta-sheets. When molecular mechanics energy minimization calculations are performed upon a triurea bearing three N-terminally linked peptide strands, a parallel beta-sheet is formed.