(2S)-2-amino-N-[[6-[[[(2S)-2-amino-3-methylbutanoyl]amino]methyl]pyridin-2-yl]methyl]-3-methylbutanamide | 1380115-26-3

• 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: (2S)-2-amino-N-[[6-[[[(2S)-2-amino-3-methylbutanoyl]amino]methyl]pyridin-2-yl]methyl]-3-methylbutanamide
• CAS: 1380115-26-3
• 化学式: C₁₇H₂₉N₅O₂
• 分子量: 335.45
• InChiKey: BYNCFMPOMKPMDI-GJZGRUSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  123
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S)-2-amino-N-[[6-[[[(2S)-2-amino-3-methylbutanoyl]amino]methyl]pyridin-2-yl]methyl]-3-methylbutanamide 、 异氰酸苯酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以70%的产率得到
  参考文献：
  名称：

  Synthesis and organogelating ability of bis-urea pseudopeptidic compounds

  摘要：

  A large family of amphiphilic pseudopeptidic derivatives in which the aliphatic tails are connected to the pseudopeptidic moiety through urea functionalities have been prepared with excellent yields. The synthetic procedure is simple and very efficient and allows a modular variation of a large number of structural parameters. The self-assembling properties of the resulting compounds has been studied under different conditions and using different media. Very interestingly, many of the compounds obtained have revealed to act as very efficient organogelators at low concentrations. The resulting gels provide some unusual properties. Of particular relevance are the broad scope of organic solvents that can be gelated and the high thermal stability of the resulting gels. Gels that are stable up to temperatures close to 100 degrees C can be obtained in some instances. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.01.007
• 作为产物：
  描述：

  2,6-双（氨基甲基）吡啶 在 氢溴酸 、 溶剂黄146 作用下， 以 乙二醇二甲醚 为溶剂， 反应 27.0h， 生成 (2S)-2-amino-N-[[6-[[[(2S)-2-amino-3-methylbutanoyl]amino]methyl]pyridin-2-yl]methyl]-3-methylbutanamide
  参考文献：
  名称：

  SN2置换中制备拟肽大环化合物的模板效应

  摘要：

  C 2的大环化反应包含中心吡啶衍生间隔基的对称对称假肽会受到不同阴离子的影响。适当阴离子的选择为制备相应的大环结构提供了极好的结果。动力学研究表明，那些阴离子的存在既提高了产率，又提高了反应速度。在B3LYP / 6-31G *水平上的计算研究使我们能够合理化实验结果。所获得的过渡态（TSs）表明，阴离子与开链假肽链之间的相互作用具有稳定作用。阴离子使涉及的两个TS稳定化：第一个涉及两个亚基之间的初始键的形成并导致开链中间体，第二个涉及环状结构的形成。−当中心间隔基衍生自2,6-双（氨基甲基）吡啶时，能够充当模板，因为它通过与两个开环形成氢键来迫使开链中间体的两端彼此接近存在于中间体中的氨基酸亚基。与第一个TS相比，这使第二个TS的稳定程度更高，因此比起竞争性的低聚反应，它更有利于大环化。计算结果还使我们能够预测新实验的结果。因此，在先前使用的优化条件下，源自2,6-二氨基吡啶的假肽大环化

  DOI：

  10.1002/chem.201101416

文献信息

• Macrocycle Synthesis by Chloride-Templated Amide Bond Formation
  作者：Vicente Martí-Centelles、M. Isabel Burguete、Santiago V. Luis

  DOI：10.1021/acs.joc.5b02676

  日期：2016.3.4

  prepared involving an anion-templated amide bond formation reaction at the macrocyclization step. Chloride anion was found to be the most efficient template in the macrocyclization process, producing improved macrocyclization yields with regard to the nontemplated reaction. The data suggest a kinetic effect of the chloride template, providing an appropriate folded conformation of the open-chain precursor

  已经制备了新的假肽大环化合物家族，其涉及在大环化步骤中阴离子模板化的酰胺键形成反应。发现氯阴离子是大环化过程中最有效的模板，与非模板化反应相比，氯代阴离子具有更高的大环化产率。数据表明了氯化物模板的动力学作用，提供了开链前体的适当折叠构象并减少了形成大环产物的能垒。
• Template Effects in SN2 Displacements for the Preparation of Pseudopeptidic Macrocycles
  作者：Vicente Martí-Centelles、M. Isabel Burguete、Santiago V. Luis

  DOI：10.1002/chem.201101416

  日期：2012.2.20

  central pyridine‐derived spacers are affected by the presence of different anions. The selection of the proper anion gives excellent results for the preparation of the corresponding macrocyclic structures. Kinetic studies show that the presence of those anions enhances both the yield and the rate of the reaction. Computational studies at the B3LYP/6‐31G* level have allowed us to rationalise the experimental

  C 2的大环化反应包含中心吡啶衍生间隔基的对称对称假肽会受到不同阴离子的影响。适当阴离子的选择为制备相应的大环结构提供了极好的结果。动力学研究表明，那些阴离子的存在既提高了产率，又提高了反应速度。在B3LYP / 6-31G *水平上的计算研究使我们能够合理化实验结果。所获得的过渡态（TSs）表明，阴离子与开链假肽链之间的相互作用具有稳定作用。阴离子使涉及的两个TS稳定化：第一个涉及两个亚基之间的初始键的形成并导致开链中间体，第二个涉及环状结构的形成。−当中心间隔基衍生自2,6-双（氨基甲基）吡啶时，能够充当模板，因为它通过与两个开环形成氢键来迫使开链中间体的两端彼此接近存在于中间体中的氨基酸亚基。与第一个TS相比，这使第二个TS的稳定程度更高，因此比起竞争性的低聚反应，它更有利于大环化。计算结果还使我们能够预测新实验的结果。因此，在先前使用的优化条件下，源自2,6-二氨基吡啶的假肽大环化
• Synthesis and organogelating ability of bis-urea pseudopeptidic compounds
  作者：Jenifer Rubio、Vicente Martí-Centelles、M. Isabel Burguete、Santiago V. Luis

  DOI：10.1016/j.tet.2013.01.007

  日期：2013.3

  A large family of amphiphilic pseudopeptidic derivatives in which the aliphatic tails are connected to the pseudopeptidic moiety through urea functionalities have been prepared with excellent yields. The synthetic procedure is simple and very efficient and allows a modular variation of a large number of structural parameters. The self-assembling properties of the resulting compounds has been studied under different conditions and using different media. Very interestingly, many of the compounds obtained have revealed to act as very efficient organogelators at low concentrations. The resulting gels provide some unusual properties. Of particular relevance are the broad scope of organic solvents that can be gelated and the high thermal stability of the resulting gels. Gels that are stable up to temperatures close to 100 degrees C can be obtained in some instances. (C) 2013 Elsevier Ltd. All rights reserved.