1-丁基-5-甲基嘧啶-2,4-二酮 | 15236-33-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 1-丁基-5-甲基嘧啶-2,4-二酮
• 英文名称: N-butylthymine
• 英文别名: 1-butylthymine；1-n-butylthymine；1-Butyl-thymin；1-Butyl-5-methyl-2,4(1H,3H)-pyrimidinedione；1-butyl-5-methylpyrimidine-2,4-dione
• CAS: 15236-33-6
• 化学式: C₉H₁₄N₂O₂
• 分子量: 182.222
• InChiKey: NUCUTLRGBQCNFA-UHFFFAOYSA-N

物化性质

• 密度：
  1.082±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,18-Dioxa-7,13,28-triazatetracyclo[17.5.3.18,12.022,26]octacosa-1(25),8(28),9,11,19(27),20,22(26),23-octaene-6,14-dione 、 1-丁基-5-甲基嘧啶-2,4-二酮 生成 1-butyl-5-methylpyrimidine-2,4-dione;2,18-dioxa-7,13,28-triazatetracyclo[17.5.3.18,12.022,26]octacosa-1(25),8(28),9,11,19(27),20,22(26),23-octaene-6,14-dione
  参考文献：
  名称：

  HAMILTON, ANDREW D.;VAN, ENGEN DONNA, J. AMER. CHEM. SOC., 109,(1987) N 16, 5035-5036

  摘要：

  DOI：
• 作为产物：
  描述：

  1,1'-di(n-butyl)thymine cis-syn 在 a methoxyindole bound to a dimer-recognizing macrocycle ⁽¹⁾ 作用下， 以 乙腈 为溶剂， 生成 1-丁基-5-甲基嘧啶-2,4-二酮
  参考文献：
  名称：

  Photosensitized pyrimidine dimer splitting by a methoxyindole bound to a dimer-recognizing macrocycle

  摘要：

  A macrocycle has been prepared that binds to a pyrimidine dimer by hydrogen bonding and photosplits the bound dimer with quantum efficiency greater than 0.1 in both protic and aprotic solvents.

  DOI：

  10.1021/jo00038a005

文献信息

• Towards a Universal Polymer Backbone: Design and Synthesis of Polymeric Scaffolds Containing Terminal Hydrogen-Bonding Recognition Motifs at Each Repeating Unit
  作者：Ludger P. Stubbs、Marcus Weck

  DOI：10.1002/chem.200390122

  日期：2003.2.17

  Polymers containing terminal hydrogen-bonding recognition motifs based on diaminotriazine and diaminopyridine groups in their side chains for the self-assembly of appropriate receptors have been prepared by ring-opening metathesis polymerization (ROMP) of norbornenes. A new synthetic method for the preparation of norbornene monomers based on pure alkyl spacers is introduced. These monomers show unprecedented

  已经通过降冰片烯的开环易位聚合（ROMP）制备了在其侧链中含有基于二氨基三嗪和二氨基吡啶基团的末端氢键识别基序的聚合物，以用于合适受体的自组装。介绍了一种基于纯烷基间隔基的降冰片烯单体合成的新方法。这些单体使用ROMP表现出空前的高反应活性。为了抑制基于二氨基三嗪的聚合物的自缔合，在N-丁基胸腺嘧啶的存在下进行聚合。丁基胸腺嘧啶通过自组装到聚合物支架的氢键位上而起保护基的作用，从而使聚合物增溶。由于二氨基吡啶单体的二聚倾向低，因此它们不需要保护基。此外，它们在单体和聚合物水平上都对氢键受体具有很高的亲和力。这些聚合物是我们设计和合成“通用聚合物支架”的第一个基础。
• Photochemical ring opening of thymidine and thymine in the presence of primary amines
  作者：Isao Saito、Hiroshi Sugiyama、Nobuyuki Furukawa、Teruo Matsuura

  DOI：10.1016/s0040-4039(01)81880-3

  日期：1981.1

  Irradiation of thymidine or thymine in the presence of tert- butylamine at 0 °C provided ping-opened photoadduct 3 which on heating at 70 °C gave 1-tert-butylthymine (2) quantitatively. Synthetic application of this photoexchange reaction with amines has been described.

  在叔丁胺的存在下于0°C照射胸腺嘧啶或胸腺嘧啶可提供开孔的光加合物3，在70°C加热后可定量得到1-叔丁基胸腺嘧啶（2）。已经描述了这种光交换反应与胺的合成应用。
• Selective Recognition of Uracil and Its Derivatives Using a DNA Repair Enzyme Structural Mimic
  作者：Yu Lin Jiang、Xiaonan Gao、Guannan Zhou、Arpit Patel、Avani Javer

  DOI：10.1021/jo901862x

  日期：2010.1.15

  uracil into its active site through hydrogen bonding and π−π stacking interactions. The reason why UDG binds only uracil tightly—and not its derivatives, such as thymine—remains unclear. In this study, we synthesized the stable, water-soluble receptor 1a as a structural mimic of the active site in UDG. Compound 1a contains a 2,6-bis(glycylamino)pyridine group, which mimics the amino acid residues of

  在DNA修复过程中，尿嘧啶DNA糖基化酶（UDG）通过氢键和π-π堆积相互作用将不需要的尿嘧啶拉入其活性位点。UDG仅与尿嘧啶紧密结合而不与尿嘧啶等衍生物紧密结合的原因仍不清楚。在这项研究中，我们合成了稳定的水溶性受体1a作为UDG活性位点的结构模拟物。化合物1a含有2，6-双（甘氨酰氨基）吡啶基团，该基团模拟UDG的氨基酸残基，该残基通过氢键网络与尿嘧啶相互作用。它也具有moiety部分作为π-π堆积相互作用元件和荧光探针，该探针模仿UDG活性位点中的芳香族基团（苯基和荧光吲哚基单元）。受体1a通过氢键和π-π堆积相互作用与尿嘧啶及其衍生物（包括胸腺嘧啶，5-甲酰基尿嘧啶，5-氟尿嘧啶和5-硝基尿嘧啶）以及一些DNA和RNA核苷（包括胸苷和尿苷）选择性结合。有趣的是，log K b关于尿嘧啶及其衍生物的N（3）H个单元的p K a值的图是线性的，负斜率（β）为-0.24±0.03。因此，N（3）H单元的p
• Highly regio- and stereoselective photocycloaddition between coumarin and thymine by molecular recognition
  作者：Keiji Mori、Osamu Murai、Shigeki Hashimoto、Yushin Nakamura

  DOI：10.1016/0040-4039(96)01981-8

  日期：1996.11

  The photoreaction of Kemp's imide-linked coumarin 1 and thymine 3 gave two crossadducts, cis-syn 4 cis-anti5. The yield and ratio of in benzene solution remarkably increased by factors of 4.2 and 10 than those in acetonitrile solution, respectively. On the other hand, the reaction of acetoxycoumarin 2 and 3 gave only the cis-anti crossadduct in each solution.

  Kemp与酰亚胺连接的香豆素1和胸腺嘧啶3的光反应产生了两个交叉加合物，顺式-顺式4顺式-反式5。苯溶液中的收率和比率分别比乙腈溶液中的收率和比率分别提高了4.2倍和10倍。另一方面，乙酰氧基香豆素2和3的反应在每种溶液中仅产生顺式-反式加合物。
• Poly(ethylene glycol)-based ammonium ionenes containing nucleobases
  作者：Mana Tamami、Sean T. Hemp、Keren Zhang、Mingqiang Zhang、Robert B. Moore、Timothy E. Long

  DOI：10.1016/j.polymer.2013.01.040

  日期：2013.3

  Adenine-functionalized ionenes (ionene-A) and thymine-functionalized ionenes (ionene-T) were synthesized from novel nucleobase-containing monomers from an efficient aza-Michael addition to an acrylate precursor. Complexes of ionenes with nucleobase-containing guest molecules (n-butyl thymine, nBT and n-butyl adenine, nBA) exhibited well-defined complementary hydrogen bonding interactions. Job's analysis revealed a 1:1 stoichiometry for the hydrogen-bonded complexes of [ionene-A]:[nBT], [ionene-T]:[nBA], and [nBA]:[nBT]. A mathematical fit of the chemical shifts to the Benesi-Hildebrand method revealed the association constants of 94 M-1, 130 M-1, and 137 M-1 for complexes of [ionene-A]:[nBT], [ionene-T]:[nBA], and [nBA]:[nBT], respectively. Furthermore, DSC thermograms of 1:1 [ionene-A/T]:[guest molecule] complexes showed the disappearance of the melting transition for the guest molecule, confirming the absence of macrophase separation of the nucleobase guest in the polymer matrix. Morphological studies including atomic force microscopy (AFM) and small-angle X-ray scattering (SAXS) revealed a microphase-separated morphology for the nucleobase-containing ionenes and less defined microphase separation for the 1:1 complexes. (C) 2013 Elsevier Ltd. All rights reserved.