methyl (2S)-2-[[3,5-bis[[(2S)-1-methoxy-3-methyl-1-oxobutan-2-yl]carbamoyl]benzoyl]amino]-3-methylbutanoate | 905751-49-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl (2S)-2-[[3,5-bis[[(2S)-1-methoxy-3-methyl-1-oxobutan-2-yl]carbamoyl]benzoyl]amino]-3-methylbutanoate
• CAS: 905751-49-7
• 化学式: C₂₇H₃₉N₃O₉
• 分子量: 549.621
• InChiKey: DEGSBKMSUPJNTE-ACRUOGEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  39
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  166
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl (2S)-2-[[3,5-bis[[(2S)-1-methoxy-3-methyl-1-oxobutan-2-yl]carbamoyl]benzoyl]amino]-3-methylbutanoate 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  l-缬氨酸衍生的1,3,5-苯-三甲酰胺类化合物作为新型超分子有机凝胶类比对介质的基础

  摘要：

  我们介绍了原始BTA单体的改良版，其中包含一个额外的l-缬氨酸部分。通过这种修改，每个单体可用的氢键受体/供体的数量增加了一倍，从而大大提高了稳定性。这样获得的新系统在低得多的BTA浓度下表现出各向异性，并且可以确定先前不相容的分析物的残留偶极偶合。

  DOI：

  10.1002/ejoc.201801306
• 作为产物：
  描述：

  L-缬氨酸 在 氯化亚砜 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 methyl (2S)-2-[[3,5-bis[[(2S)-1-methoxy-3-methyl-1-oxobutan-2-yl]carbamoyl]benzoyl]amino]-3-methylbutanoate
  参考文献：
  名称：

  Molecular self assembly of benzene-1,3,5-tricarbonyl phenylalanine

  摘要：

  Benzene-1,3,5-tricarboxylic acid derivatives with amino acids have a strong tendency to aggregate in solution. In the present communication we report a detailed study of the self assembly of these derivatives containing Phe and Val. Intermolecular hydrogen bonding, pi center dot center dot center dot pi and weak C-H center dot center dot center dot X (X = pi, O, N) interactions are involved in the process of molecular assembly. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2011.09.006

文献信息

• Supramolecular gelators based on benzenetricarboxamides for ionic liquids
  作者：Yumi Ishioka、Nami Minakuchi、Minoru Mizuhata、Tatsuo Maruyama

  DOI：10.1039/c3sm52363b

  日期：——

  Supramolecular gelators comprising 1,3,5-benzenetricarboxylic acids and amino acid methyl esters (glycine, L-alanine, L-valine, L-leucine, L-methionine, and L-phenylalanine) for ionic liquids were developed. Ten types of ionic liquids were gelated using the above-mentioned gelators at relatively low concentrations. Field emission-scanning electron microscopy and confocal laser scanning microscopy analyses revealed that these gelators self-assembled into an entangled fibrous structure in ionic liquids, leading to the gelation of the ionic liquids. Comparison studies, involving compounds analogous to the gelators, and Fourier transform infrared spectroscopy measurements suggested that hydrogen bonding played a key role in the self-assembly of the gelator molecules. The ionogels displayed reversible thermal transition characteristics and viscoelastic properties typical of a gel. The gelation of the ionic liquids studied under a wide range of gelator concentrations did not affect the intrinsic conductivity of the ionic liquids.

  开发了由 1,3,5-苯三羧酸和氨基酸甲酯（甘氨酸、L-丙氨酸、L-缬氨酸、L-亮氨酸、L-蛋氨酸和 L-苯丙氨酸）组成的离子液体超分子凝胶剂。使用上述凝胶剂以相对较低的浓度凝胶化了十种离子液体。场发射扫描电子显微镜和共聚焦激光扫描显微镜分析表明，这些凝胶剂在离子液体中自组装成缠结的纤维结构，导致离子液体凝胶化。利用与凝胶剂类似的化合物进行的对比研究和傅立叶变换红外光谱测量表明，氢键在凝胶剂分子的自组装过程中发挥了关键作用。离子凝胶显示出可逆的热转变特性和典型的凝胶粘弹特性。在多种凝胶剂浓度下研究离子液体的凝胶化现象，并未影响离子液体的内在电导率。
• Crystal habit modification of Cu(<scp>ii</scp>) isonicotinate–<i>N</i>-oxide complexes using gel phase crystallisation
  作者：Dipankar Ghosh、Katja Ferfolja、Žygimantas Drabavičius、Jonathan W. Steed、Krishna K. Damodaran

  DOI：10.1039/c8nj05036h

  日期：——

  We report the crystallisation of three forms of the copper(II) isonicotinate–N-oxide complex and their phase interconversion via solvent-mediated crystal-to-crystal transformation. The different forms of the copper complex have been isolated and characterised by single crystal X-ray diffraction. Gel phase crystallisation performed in hydrogels, low molecular weight gels and gels of a tailored gelator

  我们报告了三种形式的铜（II）异烟酸铜-N-氧化物配合物的结晶及其通过的相变溶剂介导的晶体到晶体的转化。铜络合物的不同形式已被分离出来，并通过单晶X射线衍射进行了表征。在水凝胶，低分子量凝胶和量身定制的凝胶器的凝胶中进行的凝胶相结晶显示出晶体习性的改变。在乙醇水溶液中结晶导致蓝色（I型）和绿色（II / IV型）晶体的同时形成，而使用低分子量凝胶导致蓝色I型在相同条件下选择性结晶。各种溶剂组合物中凝胶相和溶液状态结晶的比较表明，蓝色形式I在环境条件下是热力学稳定的形式。
• Formation of triple helical nanofibers using self-assembling chiral benzene-1,3,5-tricarboxamides and reversal of the nanostructure's handedness using mirror image building blocks
  作者：Partha Pratim Bose、Michael G. B. Drew、Apurba K. Das、Arindam Banerjee

  DOI：10.1039/b606371c

  日期：——

  Intertwining triple helical nanofibers with an overall handedness have been formed from self-assembling chiral benzene-1,3,5-tricarboxamides 1, 2 and 3, whereas the achiral benzene-1,3,5-tricarboxamide 4 upon self-association gives rise to straight nanofibers without any twist and transmission electron microscopy images of chiral compounds clearly demonstrate that the handedness of the triple helical nanofibers can be reversed by using the enantiomeric benzene-1,3,5-tricarboxamide building blocks.

  手性苯-1,3,5-三甲酰胺 1、2 和 3 通过自组装形成了具有整体手性的相互缠绕的三重螺旋纳米纤维，而非手性苯-1,3,5-三甲酰胺 4 通过自组装形成了没有任何扭曲的笔直纳米纤维、手性化合物的透射电子显微镜图像清楚地表明，通过使用对映体苯-1,3,5-三甲酰胺构建模块，三螺旋纳米纤维的手性可以逆转。
• Dimeric capsule vs columnar polymer: Structural factors determining the aggregation behavior of amino acid functionalized benzene-1,3,5-tricarboxamides in solution and in the solid-state
  作者：Filip Perlitius、Anna Walczak、Miroslava Čonková、Grzegorz Markiewicz、Jack Harrowfield、Artur R. Stefankiewicz

  DOI：10.1016/j.molliq.2022.120511

  日期：2022.12

  5-tricarboxamide (BTA) derivatives formed from glycine or l-valine esters (-Me, -iPr), has been investigated in the solid-state and in chloroform solution by means of several analytical methods (NMR, FT-IR, and single crystal XRD). Two types of self-assembled structures were characterized: a dimeric capsule formed by –NH···OC- (ester) bonding and a columnar assembly with characteristic –NH···OC- (amide)

  由甘氨酸或l-缬氨酸酯 (-Me, - i Pr)形成的四种苯-1,3,5-三甲酰胺 (BTA) 衍生物的非共价聚集已通过以下方法在固态和氯仿溶液中进行了研究采用多种分析方法（NMR、FT-IR 和单晶 XRD）。表征了两种类型的自组装结构：由-NH···O C-（酯）键合形成的二聚体胶囊和具有-NH···O特征的柱状组装体。C-（酰胺）键（连同单体）。深入的固态研究揭示了 C 端保护基的空间位阻在固态超分子聚集中的重要作用。增加酯基团的体积可防止分子组装成柱状结构，而是观察到二聚体组装。另一方面，它在氯仿溶液中没有影响，其中氨基酸侧链决定了自组装结果。我们的研究指出了取代基空间体积在两个位置的本质影响：氨基酸酯的 α 原子和酯基本身。对这些结构相似分子的系统研究还允许鉴定对不同相（本体、溶液）中 BTA 聚集体的性质和稳定性具有更大影响的部分。
• Molecular self assembly of benzene-1,3,5-tricarbonyl phenylalanine
  作者：Gannoju Srinivasulu、Balasubramanian Sridhar、Krishnan Ravi Kumar、Bojja Sreedhar、Venna Ramesh、Ragampeta Srinivas、Ajit C. Kunwar

  DOI：10.1016/j.molstruc.2011.09.006

  日期：2011.12

  Benzene-1,3,5-tricarboxylic acid derivatives with amino acids have a strong tendency to aggregate in solution. In the present communication we report a detailed study of the self assembly of these derivatives containing Phe and Val. Intermolecular hydrogen bonding, pi center dot center dot center dot pi and weak C-H center dot center dot center dot X (X = pi, O, N) interactions are involved in the process of molecular assembly. (C) 2011 Elsevier B.V. All rights reserved.