N-((ethoxycarbonyl)methyl)-5-amino-2-(octyloxy)benzamide | 267897-52-9

• 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: N-((ethoxycarbonyl)methyl)-5-amino-2-(octyloxy)benzamide
• 英文别名: Ethyl 2-[(5-amino-2-octoxybenzoyl)amino]acetate
• CAS: 267897-52-9
• 化学式: C₁₉H₃₀N₂O₄
• 分子量: 350.458
• InChiKey: XEFQOSYHFVJIFA-UHFFFAOYSA-N

物化性质

• 沸点：
  503.1±50.0 °C(Predicted)
• 密度：
  1.079±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  25
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  90.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-((ethoxycarbonyl)methyl)-5-amino-2-(octyloxy)benzamide 在 palladium on activated charcoal 盐酸 、 sodium hydroxide 、 氢气 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.5h， 生成 3-[2-((S)-2-Benzyloxycarbonylamino-3-phenyl-propionylamino)-acetylamino]-5-[2-(5-hexanoylamino-2-octyloxy-benzoylamino)-acetylamino]-benzoic acid octyl ester
  参考文献：
  名称：

  A Noncovalent Approach to Antiparallel β-Sheet Formation

  摘要：

  Four tripeptide chains, when attached to the same end of a hydrogen-bonded duplex (1.2) with the unsymmetrical, complementary sequences of ADAA/DADD, have been brought into proximity, leading to the formation of four hybrid duplexes, 1a.2a, 1a.2b, 1b.2a, and 1b.2b, each of which contains a two-stranded beta-sheet segment. The extended conformations of the peptide chains were confirmed by 1D and 2D NMR. The peptide strands stay registered through hydrogen bonding and the beta-sheets are stabilized by side chain interactions. Two-dimensional NMR data also indicate that the duplex template prevents further aggregation in the peptide segment. When the peptide chains are attached to the two different termini of the duplex template, NMR studies show the presence of a mixture with no clearly defined conformations. In the absence of the duplex template, the tripeptides are found to associate randomly. Finally, isothermal titration calorimetry studies revealed that the hybrid duplex 1a.2a was more stable than either the duplex template or the peptides alone.

  DOI：

  10.1021/ja010701b
• 作为产物：
  描述：

  2-羟基-5-硝基苯甲酸甲酯 在 palladium on activated charcoal sodium hydroxide 、 氢气 、 potassium carbonate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 生成 N-((ethoxycarbonyl)methyl)-5-amino-2-(octyloxy)benzamide
  参考文献：
  名称：

  使用拟肽 β-片层模块进行定义明确的仿生模块化多域聚合物的合成和单分子研究

  摘要：

  为了追求兼具强度、韧性和弹性的先进生物材料，人们合成了一类新的定义明确的模块化聚合物，并使用原子力显微镜研究了它们的纳米力学性能。这些聚合物基于基于拟肽β-折叠的双闭环 (DCL) 模块，该模块旨在克服我们之前报道的模块化聚合物的局限性 (J. Am. Chem. Soc. 2004, 126, 2059) . 单分子力扩展实验表明，随着聚合物被拉伸，这些模块会依次展开，从而产生更规则的锯齿状曲线，类似于在肌动蛋白和其他生物聚合物中看到的曲线。单分子数据与计算机建模非常吻合，

  DOI：

  10.1021/ja0448871

文献信息

• Highly Ordered Nanoporous Films from Supramolecular Diblock Copolymers with Hydrogen-Bonding Junctions
  作者：Damien Montarnal、Nicolas Delbosc、Cécile Chamignon、Marie-Alice Virolleaud、Yingdong Luo、Craig J. Hawker、Eric Drockenmuller、Julien Bernard

  DOI：10.1002/anie.201504838

  日期：2015.9.14

  PMMA supramolecular polymers with molecular weights up to 30 kg mol−1 are synthesized and shown to form highly stable supramolecular diblock copolymers (BCPs) when mixed, in non‐polar solvents or in the bulk. Hierarchical self‐assembly of such supramolecular BCPs by thermal annealing affords morphologies with excellent lateral order, comparable to features expected from covalent diblock copolymer analogues

  我们设计了有效的前体，该前体将互补的缔合基团与出色的结合亲和力和硫代羰基硫基团结合在一起，从而实现了精确的RAFT聚合。分子量高达30 kg mol -1的定义明确的PS和PMMA超分子聚合物合成后显示在非极性溶剂或本体中混合时会形成高度稳定的超分子二嵌段共聚物（BCP）。此类超分子BCP通过热退火的分层自组装可提供具有优异侧向顺序的形貌，可与共价二嵌段共聚物类似物预期的特征相媲美。用质子溶剂简单洗涤所得材料会破坏超分子缔合，并选择性地溶解一种聚合物，从而提供了一种制备顺序良好的纳米多孔材料的简单方法，而无需进行交联或侵入性化学降解。
• A Highly Stable, Six-Hydrogen-Bonded Molecular Duplex
  作者：Huaqiang Zeng、Rebecca S. Miller、Robert A. Flowers、Bing Gong

  DOI：10.1021/ja9942742

  日期：2000.3.1

  This paper describes the design, synthesis, and characterization of a hydrogen-bonded molecular duplex (3·4). Two oligoamide molecular strands, 3 and 4, with the complementary hydrogen-bonding sequences ADAADA and DADDAD, respectively, were found to form an extremely stable (Ka = (1.3 ± 0.7) × 109 M-1) molecular duplex (3·4) in chloroform. Evidence from 1D and 2D 1H NMR spectroscopy, isothermal titration

  本文描述了氢键分子双链体 (3·4) 的设计、合成和表征。发现分别具有互补氢键序列 ADAADA 和 DADDAD 的两条寡酰胺分子链 3 和 4 形成极其稳定的 (Ka = (1.3 ± 0.7) × 109 M-1) 分子双链体 (3·4)在氯仿中。来自 1D 和 2D 1H NMR 光谱、等温滴定量热法和薄层色谱的证据证实了双链体的形成和高稳定性。众多氢键和范德华相互作用之间的正协同作用以及分子内氢键对单个链的预组织可以解释这种特殊的稳定性。这种设计为具有可编程特异性和稳定性的超分子识别单元开辟了一条新途径。
• Sequence Specificity of Hydrogen-Bonded Molecular Duplexes
  作者：Huaqiang Zeng、Harold Ickes、Robert A. Flowers、Bing Gong

  DOI：10.1021/jo010250d

  日期：2001.5.1

  perfectly hydrogen-bonded duplex 1.2. These NMR and ITC results indicate that the pairing of two complementary single strands is not affected by another very similar single strand that contains only one wrong H-bond donor or acceptor, which demonstrates that the self-assembly of this class of H-bonded duplexes is a highly sequence-specific process. The role of these H-bonded duplexes as predictable and programmable

  基于双链体1.2设计并合成了氢键结合的分子双链体1.3和1.4，它们各自包含一个不匹配的结合位点（1.3中的受体对受体，以及1.4中的供体对受体）。一维和二维NMR研究表明，尽管存在单个错配的结合位点，但双链体1.3和1.4的骨架仍通过形成其余五个H键而保持对准。1.3和1.4的骨架通过在这些位点周围轻微扭曲而调整为存在不匹配的结合位点，从而减轻了两个H键供体（酰胺O）之间或两个受体（酰胺H）之间的正面排斥性相互作用。将1当量的单链2与单链1形成完美匹配的双链体1.2后，添加到1.3或1.4的溶液中，仅添加1.2和单链3或4，被检测到。等温滴定量热法（ITC，在含5％DMSO的氯仿中）表明，双链体1.3和1.4的稳定性比相应的氢键结合的双链体1.2的稳定性差（> 40倍）。这些NMR和ITC结果表明，两条互补单链的配对不受另一条非常相似的单链的影响，后者仅包含一个错误的H键供体或受体，这表
• Oligoamide Duplexes as Organogelators
  作者：Ruikai Cao、Jingjing Zhou、Wei Wang、Wen Feng、Xianghui Li、Penghui Zhang、Pengchi Deng、Lihua Yuan、Bing Gong

  DOI：10.1021/ol100953e

  日期：2010.7.2

  Oligoamide duplexes carrying multiple alkyl side chains were found to serve as gelators for aromatic solvents. The double-stranded backbone was essential for the hierarchical self-assembly of the molecular duplex into fibers of high aspect ratios. The demonstrated gelating abilities may be extended to a large family of analogous H-bonded duplexes having different H-bonding sequences, leading to a unique platform for developing a diverse variety of potential gelators based on a supramolecular and/or a dynamic covalent approach.
• Interplay of Olefin Metathesis and Multiple Hydrogen Bonding Interactions: Covalently Cross-linked Zippers
  作者：Jisen Zeng、Wei Wang、Pengchi Deng、Wen Feng、Jingjing Zhou、Yuanyou Yang、Lihua Yuan、Kazuhiro Yamato、Bing Gong

  DOI：10.1021/ol201282d

  日期：2011.8.5

  Hydrogen-bonded zippers bearing terminal alkene groups were treated with Grubbs' catalyst, leading to covalently cross-linked zippers without violating H-bonding sequence specificity. The yield of a cross-linked zipper depended on the stability of its H-bonded precursor, with a weakly associating pair giving reasonable yields only at high concentrations while strongly associating pairs showed nearly quantitative yields. The Integration of thermodynamic (H-bonding) and kinetic (irreversible C=C bond formation) processes suggests the possibility of developing many different covalent association units for constructing molecular structures based on a self-assembling way.