N-(6-乙酰氨基-4-氧代-1H-吡啶-2-基)乙酰胺 | 134456-96-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: N-(6-乙酰氨基-4-氧代-1H-吡啶-2-基)乙酰胺
• 英文名称: 2,6-diacetamido-4-hydroxypyridine
• 英文别名: 2,6-bis(acylamino)-4-pyridone；2,6-diacetamido-4-pyridone；Acetamide, N,N'-(4-hydroxy-2,6-pyridinediyl)bis-；N-(6-acetamido-4-oxo-1H-pyridin-2-yl)acetamide
• CAS: 134456-96-5
• 化学式: C₉H₁₁N₃O₃
• 分子量: 209.205
• InChiKey: AXMGBCVBEKISLF-UHFFFAOYSA-N

物化性质

• 沸点：
  731.1±60.0 °C(Predicted)
• 密度：
  1.420±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  87.3
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(6-乙酰氨基-4-氧代-1H-吡啶-2-基)乙酰胺 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 potassium tert-butylate 、 二正丁胺 作用下， 反应 16.0h， 生成
  参考文献：
  名称：

  Artificial allosteric receptors for nucleotide bases and alkali-metal cations

  摘要：

  New allosteric thymine receptors, 2,6-diamidopyridine derivatives tethered to an anthracene ring by a polyoxyethylene chain, were synthesized. In these receptors, binding of 1-butylthymine was enhanced by a factor of 4-6 by recognition of sodium cations, and the changes in the electron density of the anthracene ring were found to have influence on the allosterism by through-space interaction. The anthracene-linked diamidopyridines represent a rationally designed new class of artificial allosteric receptors.

  DOI：

  10.1021/ja00071a021
• 作为产物：
  描述：

  4-羟基吡啶 在 碳酸氢钠 、 sodium amide 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 paraffin 为溶剂， 反应 19.0h， 生成 N-(6-乙酰氨基-4-氧代-1H-吡啶-2-基)乙酰胺
  参考文献：
  名称：

  A new versatile synthesis of 4-substituted diaminopyridine derivatives

  摘要：

  A new convenient method for the synthesis of substituted 2,6-diacetamido pyridines has been developed. It starts from 4-hydroxypyridine and comprises the introduction of the amino groups by the Chichibabin reaction. After several protection and deprotection steps 2,6-diacetamido-4-hydroxy pyridine is obtained, which is regarded as a key compound for the synthesis of various substituted 2,6-diacetamido pyridines. It is shown that the free hydroxy group is susceptible for nucleophilic substitution. This provides an easy access to the introduction of different functional groups at 4-position of 2,6-diacetamido pyridine. The advantages over other procedures described in the literature are discussed. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.02.089

文献信息

• New molecular complements to imides. Complexation of thymine derivatives
  作者：Tae Kyo Park、Joseph Schroeder、Julius Rebek

  DOI：10.1021/ja00013a093

  日期：1991.6

  We describe here new systems for base-pairing to thymines which offer unusual affinities and promise for the catalysis of reactions involving thymines

  我们在这里描述了与胸腺嘧啶碱基配对的新系统，它提供了不同寻常的亲和力，并有望催化涉及胸腺嘧啶的反应
• Nucleobase Recognition by Artificial Receptors Possessing a Ferrocene Skeleton as a Novel Modular Unit for Hydrogen Bonding and Stacking Interactions
  作者：Masahiko Inouye、Yutaka Hyodo、Hiroyuki Nakazumi

  DOI：10.1021/jo982138u

  日期：1999.4.1

  Novel ferrocene-modified artificial nucleobase receptors were designed and synthesized. The nucleobase receptors possess hydrogen-bonding and pi-stacking interaction sites that act simultaneously for binding to 1-butylthymine utilizing the pivot character of the ferrocene skeleton. Diamidopyridine was chosen for the hydrogen-bonding moiety, and various polynuclear aromatics were used for pi-stacking one. The two components were tethered to the cyclopentadienyl rings via ethynediyl and oxymethylene spacers. The binding affinity of the receptors to 1-butylthymine was found to be dependent on the aromatic structures. Thus, the association constants for perylene-linked receptors were approximately doubled compared to those of aromatic-free ones, an energy difference of similar to 0.5 kcal/mol. Detailed comparisons between the 10 receptors clarified the value of the pivot character of the ferrocene for construction of the intermolecular interaction site.
• Glassy dynamics of hydrogen-bonded heteroditopic molecules
  作者：Nan Lou、YangYang Wang、Haixia Li、Alexei P. Sokolov、Huiming Xiong

  DOI：10.1016/j.polymer.2012.07.052

  日期：2012.9

  A self-complementary heteroditopic molecule composed of thymine and diamidopyridine end groups and a flexible aliphatic interconnecting chain has been synthesized. The glassy dynamics of this hydrogen-bonded supramolecule have been investigated by using dielectric and rheological measurements, in combination with infra-red spectroscopy and solid-state C-13 NMR experiments. Decoupling of main dielectric relaxation from viscosity has been found in the vicinity of the glass transition and the temperature dependence of viscosity appears to be stronger than that of dielectric relaxation. The unusual dynamic decoupling phenomenon is ascribed to the chemical/dynamic heterogeneity and formation of hydrogen bonds in the supramolecules. (C) 2012 Elsevier Ltd. All rights reserved.
• STEREO- AND REGIOSELECTIVE PHOTOCYCLOADDITION OF COUMARIN AND THYMINE DERIVATIVES USING MOLECULAR RECOGNITION CATALYST
  作者：Osamu Murai、Hisafumi Ikeda、Yushin Nakamura

  DOI：10.1515/hc.2002.8.5.469

  日期：2002.1
• PARK, TAE KYO;SCHROEDER, JOSEPH;REBEK, JULIUS (JR), J. AMER. CHEM. SOC., 113,(1991) N3, C. 5125-5127
  作者：PARK, TAE KYO、SCHROEDER, JOSEPH、REBEK, JULIUS (JR)

  DOI：——

  日期：——