heptanoic acid (7-amino-[1,8]naphthyridin-2-yl)amide | 873795-58-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: heptanoic acid (7-amino-[1,8]naphthyridin-2-yl)amide
• 英文别名: heptanoic acid (7-amino-1,8-naphthyridin-2-yl)amide；N-(7-amino-1,8-naphthyridin-2-yl)heptanamide
• CAS: 873795-58-5
• 化学式: C₁₅H₂₀N₄O
• 分子量: 272.35
• InChiKey: ZGKYGUIRIYHIQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  80.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  heptanoic acid (7-amino-[1,8]naphthyridin-2-yl)amide 在 4-二甲氨基吡啶 、 四氯化钛 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 heptanoic acid [7-(6-hydroxyhexanoylamino)-[1,8]naphthyridin-2-yl]amide
  参考文献：
  名称：

  A Quadruply Hydrogen Bonded Heterocomplex Displaying High-Fidelity Recognition

  摘要：

  An exceptionally strong quadruply hydrogen-bonded complex is formed between 2,7-diamido-1,8-naphthyridine 3 (DAN) and the butylurea of guanosine 6 (UG) in chloroform. The UG unit can be prepared in four steps from guanosine on a 10 g scale in excellent yields without chromatographic purification. The association constant (K-assoc approximate to 5 x 10(7) m(-1)) for the UG(.)DAN complex determined by fluorescence energy transfer from the naphthyridine unit of 3 to coumarin 343 covalently linked UG (18) is among the highest reported for a neutral DNA base-pair analogue. The weak self-association of DAN (K-dimer < 10 m(-1)) and UG (K-dimer ca. 200-300 m(-1)) means that the UG-DAN complex forms with unparalleled fidelity.

  DOI：

  10.1021/ja0545517
• 作为产物：
  描述：

  N-(7-bromo-1,8-naphthyridin-2-yl)heptanamide 在 copper(I) oxide 、 ammonium hydroxide 作用下， 以 乙二醇二甲醚 、 水 、 乙二醇 为溶剂， 反应 24.0h， 以53%的产率得到heptanoic acid (7-amino-[1,8]naphthyridin-2-yl)amide
  参考文献：
  名称：

  室温下溴铵吡啶与铜的氨水铜催化胺化

  摘要：

  据报道，室温下，铜催化的氨基-溴-1,8-萘啶胺的胺化反应。在环境温度下使用Cu 2 O和氨水可提供10-87％产率的胺化产物。通过用三溴化磷处理of啶并吡啶酮，可以制备15-65％产率的溴萘并吡啶。这种方法为功能性，非对称的2,7-diamido-1,8-naphthyridines提供了另一种途径。

  DOI：

  10.1021/jo100476x

文献信息

• Azobenzene dye-coupled quadruply hydrogen-bonding modules as colorimetric indicators for supramolecular interactions
  作者：Yagang Zhang、Steven C Zimmerman

  DOI：10.3762/bjoc.8.55

  日期：——

  The facile coupling of azobenzene dyes to the quadruply hydrogen-bonding modules 2,7-diamido-1,8-naphthyridine (DAN) and 7-deazaguanine urea (DeUG) is described. The coupling of azobenzene dye 2 to mono-amido DAN units 4, 7, and 9 was effected by classic 4-(dimethylamino)pyridine (DMAP)-catalyzed peptide synthesis with N-(3-dimethylaminopropyl)-N’-ethyl carbodiimide hydrochloride (EDC) as activating agent, affording the respective amide products 5, 8, and 10 in 60–71% yield. The amide linkage was formed through either the aliphatic or aromatic ester group of 2, allowing both the flexibility and absorption maximum to be tuned. Azobenzene dye 1 was coupled to the DeUG unit 11 by Steglich esterification to afford the product amide 12 in 35% yield. Alternatively, azobenzene dye 16 underwent a room-temperature copper-catalyzed azide–alkyne Huisgen cycloaddition with DeUG alkyne 17 to give triazole 18 in 71% yield. Azobenzene coupled DAN modules 5, 8, and 10 are bright orange–red in color, and azobenzene coupled DeUG modules 12 and 18 are orange–yellow in color. Azobenzene coupled DAN and DeUG modules were successfully used as colorimetric indicators for specific DAN–DeUG and DAN–UPy (2-ureido-4(1H)-pyrimidone) quadruply hydrogen-bonding interactions.

  本文描述了将偶氮苯染料与四重氢键模块2,7-二氨基-1,8-萘啶（DAN）和7-去氧鸟嘌呤脲（DeUG）轻松耦合的方法。通过经典的4-(二甲氨基)吡啶（DMAP）催化的肽合成，使用N-(3-二甲氨基丙基)-N'-乙基碳酰亚胺盐酸盐（EDC）作为活化剂，将偶氮苯染料2与单氨基DAN单元4、7和9偶联，得到相应的酰胺产物5、8和10，收率为60-71%。酰胺连接通过2的脂肪族或芳香族酯基形成，从而实现了灵活性和吸收最大值的调节。偶氮苯染料1通过Steglich酯化与DeUG单元11偶联，得到产物酰胺12，收率为35%。另外，偶氮苯染料16与DeUG炔基17在室温下进行铜催化的偶氮-炔Huisgen环加成反应，得到三唑18，收率为71%。偶氮苯偶联的DAN模块5、8和10呈亮橙红色，偶氮苯偶联的DeUG模块12和18呈橙黄色。偶氮苯偶联的DAN和DeUG模块成功地用作特定DAN-DeUG和DAN-UPy（2-脲基-4（1H）-嘧啶酮）四重氢键相互作用的比色指示剂。
• A Supramolecular Multi-Block Copolymer with a High Propensity for Alternation
  作者：Taiho Park、Steven C. Zimmerman

  DOI：10.1021/ja064116s

  日期：2006.11.1

  Alternating, multi-block supramolecular copolymers were created using quadruple hydrogen bonding as the noncovalent binding force. One block consisted of two guanosine butyl urea (UG) units attached at the ends of a triethylene glycol linker or a PEG chain (MW = 2 kD). The other block contained a 2,7-diamido-1,8-naphthyridine (DAN) unit at each end of a short alkane diester linker or a 100 kD poly(butyl methacrylate) macromolecule. The UG unit presents an ADDA hydrogen bonding array that is complementary to the DAAD array of DAN, and these form a very strong complex (Kassoc approximately 5 x 107 M-1), whereas UG and DAN weakly self-associate. These recognition properties allowed a multi-block supramolecular polymer to form which exhibits a high propensity for alternation. The self-assembled polymeric structure was shown to be reversibly formed and it was characterized by a combination of dynamic light scattering (DLS), 1H NMR, size exclusion chromatography (SEC), and viscometry.
• Formation of a Miscible Supramolecular Polymer Blend through Self-Assembly Mediated by a Quadruply Hydrogen-Bonded Heterocomplex
  作者：Taiho Park、Steven C. Zimmerman

  DOI：10.1021/ja0631854

  日期：2006.9.1

  A supramolecular network polymer consisting of a pair of immiscible polymers, poly( butyl)methacrylate ( PBMA) and polystyrene ( PS), is described. A urea of guanosine ( 1, UG) and 2,7-diamido1,8-naphthyridine ( 2, DAN), which form an exceptionally strong quadruply hydrogen-bonding complex, are displayed at 1-10 mol % along the main backbone of PBMA and PS, respectively. H-1 NMR studies show heterocomplexation between UG and DAN exclusively. This high-fidelity, high- affinity supramolecular connection of two different polymer coils at the molecular level produces a polymer blend. Blends containing different weight ratios of the polymers and mole percent of the recognition units were characterized by AFM and DSC experiments with no isolated domains observed and a single glass-transition temperature ( T-g). The T-g is tunable by varying the weight ratio of the polymers in the blend. In addition, viscosity measurements, size-exclusion chromatography ( SEC), and dynamic light-scattering ( DLS) studies demonstrate the formation of a supramolecular network structure.
• Room Temperature, Copper-Catalyzed Amination of Bromonaphthyridines with Aqueous Ammonia
  作者：Cyrus A. Anderson、Phillip G. Taylor、Mary A. Zeller、Steven C. Zimmerman

  DOI：10.1021/jo100476x

  日期：2010.7.16

  Room temperature, copper-catalyzed amination of amido-bromo-1,8-naphthyridines is reported. Use of Cu2O and aqueous ammonia at ambient temperature affords amination products in 10−87% yield. Bromonaphthyridines are prepared in 15−65% yield via treatment of amidonaphthyridinones with phosphorus tribromide. This methodology provides an alternative route to functional, nonsymmetric 2,7-diamido-1,8-naphthyridines

  据报道，室温下，铜催化的氨基-溴-1,8-萘啶胺的胺化反应。在环境温度下使用Cu 2 O和氨水可提供10-87％产率的胺化产物。通过用三溴化磷处理of啶并吡啶酮，可以制备15-65％产率的溴萘并吡啶。这种方法为功能性，非对称的2,7-diamido-1,8-naphthyridines提供了另一种途径。
• A Quadruply Hydrogen Bonded Heterocomplex Displaying High-Fidelity Recognition
  作者：Taiho Park、Eric M. Todd、Shoji Nakashima、Steven C. Zimmerman

  DOI：10.1021/ja0545517

  日期：2005.12.1

  An exceptionally strong quadruply hydrogen-bonded complex is formed between 2,7-diamido-1,8-naphthyridine 3 (DAN) and the butylurea of guanosine 6 (UG) in chloroform. The UG unit can be prepared in four steps from guanosine on a 10 g scale in excellent yields without chromatographic purification. The association constant (K-assoc approximate to 5 x 10(7) m(-1)) for the UG(.)DAN complex determined by fluorescence energy transfer from the naphthyridine unit of 3 to coumarin 343 covalently linked UG (18) is among the highest reported for a neutral DNA base-pair analogue. The weak self-association of DAN (K-dimer < 10 m(-1)) and UG (K-dimer ca. 200-300 m(-1)) means that the UG-DAN complex forms with unparalleled fidelity.