terephthaloyldi(L-leucine methyl ester) | 668479-45-6

• 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: terephthaloyldi(L-leucine methyl ester)
• 英文别名: dimethyl 2,2′-(terephthaloylbis(azanediyl))bis(4-methylpentanoate)；methyl (2S)-2-[[4-[[(2S)-1-methoxy-4-methyl-1-oxopentan-2-yl]carbamoyl]benzoyl]amino]-4-methylpentanoate
• CAS: 668479-45-6
• 化学式: C₂₂H₃₂N₂O₆
• 分子量: 420.506
• InChiKey: XNHHXDOBMGMRRH-ROUUACIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  30
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  terephthaloyldi(L-leucine methyl ester) 在 lithium hydroxide 、 N,N'-二异丙基碳二亚胺 作用下， 以 乙二醇二甲醚 、 二氯甲烷 为溶剂， 反应 19.0h， 生成 terephthaloyldi(L-leucyl-L-proline methyl ester)
  参考文献：
  名称：

  Syntheses and Different Chemical Behaviour of Precursors of Putative Dibasic Inhibitors of Human Mast Cell Tryptase

  摘要：

  Choosing the best conditions and pathways for the synthesis of peptidic compounds remains a challenge for the peptide chemist. Our efforts towards the syntheses of two precursors of potential tryptase inhibitors, building block A and B, led to the development of two different synthesis routes. Each of them is successful in the synthesis of only one of the two, structurally nearly identical target compounds.

  DOI：

  10.1007/s00706-003-0029-x
• 作为产物：
  描述：

  L-亮氨酸甲酯盐酸盐 、 对苯二甲酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以64%的产率得到terephthaloyldi(L-leucine methyl ester)
  参考文献：
  名称：

  对苯二甲酸和苯1,2,3-三羧酸的五个氨基酸共轭物的晶体结构和氢键分析†

  摘要：

  四个直线连接氨基酸衍生的配体，1-4，和一个潜在的三个连接，5，通过适当的对苯二甲酰氯或三氯化苯-1,3,5-三羰基与保护的氨基酸甲基酯的反应制备。这里使用的氨基酸是丙氨酸（1，5），异亮氨酸（2），亮氨酸（3）和缬氨酸（4）。四种氨基酸取代的对苯二甲酰胺（2,2'-（对苯二甲酰基双（氮杂二基））二丙酸二水合物1 ; 2,2'-（对苯二甲酰基双（氮杂二基））双（3-甲基戊酸）一水合物2的晶体形式; 2,2'-（对苯二甲酰基双（氮杂二基））双（4-甲基戊酸）二水合物3 ; 2,2'-（对苯二甲酰基双（氮杂二基））双（3-甲基丁酸）二水合物4）和一个苯-1,3,5-三甲苯酰胺分子（2,2'，2''-（（苯-1,3表征了5-（5-三羰基）三（氮杂二烷基）三丙酸半水合物5），并解析了单晶结构。所有化合物均形成氢键2D和3D网络。线性连接的氨基酸衍生物可以根据氢键模式和最终结构分为三类。化合物1和2

  DOI：

  10.1039/c4ce00605d

文献信息

• Nanostaircase formation in the solid state from self-assembling synthetic terephthalamides with a common molecular scaffold
  作者：Sudipta Ray、Raghurama P. Hegde、Apurba Kumar Das、N. Shamala、Arindam Banerjee

  DOI：10.1016/j.tet.2006.07.092

  日期：2006.10

  The design and construction of nanostructured materials using proper self-assembling molecular building blocks is a real challenge to scientists. Here, we present the formation of a new nano-architecture, i.e., nanostaircase in the solid state by using molecular building blocks, which are amenable to self-assembly in a directed manner to form the specific nanostructure. The molecular building blocks are terephthalamides 1-4, which are bis-terephthalamides of methyl esters of various alpha-amino acids including L-leucine 1, D-leucine 2, L-isoleucine 3, and alpha-aminoisobutyric acid (Aib) 4. All terephthalamides presented here, irrespective of their different side chain residues or stereochemistry, self-assemble to form supramolecular nanostaircase structures in crystals. Each terephthalamide contains two good hydrogen-bond donors and two hydrogen-bond acceptors. Two N-H center dot center dot center dot O hydrogen bonds and C-H center dot center dot center dot pi interactions are responsible for the formation and stabilization of the nanostaircase structures in crystals. The molecular building blocks are packed orthogonally to each other in crystals and this arrangement can help the formation of nanostaircase structure upon self-assembly. (c) 2006 Elsevier Ltd. All rights reserved.
• Syntheses and Different Chemical Behaviour of Precursors of Putative Dibasic Inhibitors of Human Mast Cell Tryptase
  作者：Gregor Radau

  DOI：10.1007/s00706-003-0029-x

  日期：2003.8.1

  Choosing the best conditions and pathways for the synthesis of peptidic compounds remains a challenge for the peptide chemist. Our efforts towards the syntheses of two precursors of potential tryptase inhibitors, building block A and B, led to the development of two different synthesis routes. Each of them is successful in the synthesis of only one of the two, structurally nearly identical target compounds.
• Crystal structures and hydrogen bond analysis of five amino acid conjugates of terephthalic and benzene-1,2,3-tricarboxylic acids
  作者：Anirban Karmakar、Clive L. Oliver、Ana E. Platero-Prats、Elina Laurila、Lars Öhrström

  DOI：10.1039/c4ce00605d

  日期：——

  were characterised and the single crystal structures were solved. All the compounds form hydrogen bonded 2D and 3D nets. Linear connecting amino acid derivatives can be categorised into three groups depending on the hydrogen bond patterns and final structures. Compounds 1 and 2 form 3D structures but the final structure is different due to the different hydrogen bond synthons. Compounds 3 and 4 are isostructural

  四个直线连接氨基酸衍生的配体，1-4，和一个潜在的三个连接，5，通过适当的对苯二甲酰氯或三氯化苯-1,3,5-三羰基与保护的氨基酸甲基酯的反应制备。这里使用的氨基酸是丙氨酸（1，5），异亮氨酸（2），亮氨酸（3）和缬氨酸（4）。四种氨基酸取代的对苯二甲酰胺（2,2'-（对苯二甲酰基双（氮杂二基））二丙酸二水合物1 ; 2,2'-（对苯二甲酰基双（氮杂二基））双（3-甲基戊酸）一水合物2的晶体形式; 2,2'-（对苯二甲酰基双（氮杂二基））双（4-甲基戊酸）二水合物3 ; 2,2'-（对苯二甲酰基双（氮杂二基））双（3-甲基丁酸）二水合物4）和一个苯-1,3,5-三甲苯酰胺分子（2,2'，2''-（（苯-1,3表征了5-（5-三羰基）三（氮杂二烷基）三丙酸半水合物5），并解析了单晶结构。所有化合物均形成氢键2D和3D网络。线性连接的氨基酸衍生物可以根据氢键模式和最终结构分为三类。化合物1和2