heptanoic acid [7-(6-hydroxyhexanoylamino)-[1,8]naphthyridin-2-yl]amide | 873795-56-3

• 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-(6-hydroxyhexanoylamino)-[1,8]naphthyridin-2-yl]amide
• CAS: 873795-56-3
• 化学式: C₂₁H₃₀N₄O₃
• 分子量: 386.494
• InChiKey: YPVUFHJXXIWKMQ-UHFFFAOYSA-N

物化性质

• 沸点：
  691.9±55.0 °C(Predicted)
• 密度：
  1.199±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.03
• 重原子数：
  28.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  104.21
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  heptanoic acid [7-(6-hydroxyhexanoylamino)-[1,8]naphthyridin-2-yl]amide 、 香豆素 343 在 4-二甲氨基吡啶 、 TEA 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以25%的产率得到
  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：

  6-(2-methoxyethoxymethoxy)hexanoic acid 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

文献信息

• 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.