1-vinylthymine | 20245-84-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-vinylthymine
• 英文别名: vinyl thymine；5-methyl-1-vinylpyrimidine-2,4(1H,3H)-dione；N¹-vinylthymine；2,4(1H,3H)-Pyrimidinedione, 1-ethenyl-5-methyl-；1-ethenyl-5-methylpyrimidine-2,4-dione
• CAS: 20245-84-5
• 化学式: C₇H₈N₂O₂
• 分子量: 152.153
• InChiKey: JUCQIDYDXCHRKC-UHFFFAOYSA-N

物化性质

• 熔点：
  205-207 °C
• 密度：
  1.282±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  1-vinylthymine 在 氢氟酸 、 异氰酸苯酯 、 三乙胺 作用下， 以 乙腈 、 苯 为溶剂， 反应 121.0h， 生成 1-(3-Hydroxymethyl-4,5-dihydro-isoxazol-5-yl)-5-methyl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Heterocyclic Nucleosede Analogues by Cycloaddition Reactions of 1-Vinylthymine with 1,3-Depoles

  摘要：

  1,3-Dipolar cycloaddition of 1-vinylthymine to azides, nitrile oxides, nitrones and nitronates has been investigated as a route to heterocyclic nucleoside analogues in which the nucleoside ribose moiety has been replaced by an alternative heterocycle. Reaction of 1-vinylthymine with highly reactive nitrile oxides affords 1(isoxazolin-5-yl)thymine products in excellent yield at room temperature. The less reactive nitrone dipoles undergo cycloaddition to 1-vinylthymine at elevated temperature to afford 1-(isoxazolidin-5-yl)thymine cycloadducts in good-to-moderate yields, but show a tendency to eliminate thymine from the cycloaddition products over long reaction times. Azide cycloadditions to 1-vinylthymine proceed only under forcing conditions to which the fragile triazoline products are unstable.

  DOI：

  10.1080/07328319808004220
• 作为产物：
  描述：

  5-Methyl-1-[3-(tetrahydro-pyran-2-yloxymethyl)-4,5-dihydro-isoxazol-5-yl]-1H-pyrimidine-2,4-dione 在 sodium hydroxide 、 氯化亚砜 、 Dowex 50 (H+) 、 potassium tert-butylate 、 氨 作用下， 以 1,4-二氧六环 、 吡啶 、 甲醇 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.5h， 生成 1-vinylthymine
  参考文献：
  名称：

  二氢异恶唑核苷和核苷酸类似物的合成。

  摘要：

  二氢异恶唑核苷及其膦酸酯衍生物可通过腈氧化物与相应的乙烯基核苷碱基的1，3-偶极环加成反应有效地制备，以进行抗病毒研究。

  DOI：

  10.1021/jo961779r

文献信息

• 1,3-Dipolar cycloaddition in the synthesis of trifluoromethyl-substituted isoxazolidinyl derivatives of nucleobases
  作者：Mateusz Kuprianowicz、Marcin Kaźmierczak、Emilia Muszyńska、Klaudia Bzdęga、Hanna Wójtowicz-Rajchel

  DOI：10.1016/j.jfluchem.2018.05.009

  日期：2018.8

  conveniently prepared in moderate or good yields by direct 1,3-dipolar cycloaddition. Isoxazolidines 5-7 derived from fluorinated N-vinyl nucleobases and N-alkyl-methylenenitrones were obtained with complete regiocontrol and stereocontrol and the reactions proceeded with full transfer of the dipolarophile geometry to the cycloadduct. The cycloaddition reactions of N-alkyl-trifluoromethylnitrones with N-vinyl

  通过直接的1，3-偶极环加成，以中等或良好的收率方便地制备了两个系列的含三氟甲基的非羟基异恶唑啉基核苷类似物。异恶唑烷5 - 7从氟化衍生ñ -乙烯基核碱基和ñ -烷基methylenenitrones用完整区域控制和立体控制，并与亲偶极几何的充分转移到环加成进行反应而获得。N-烷基三氟甲基亚硝基与N-乙烯基核碱基的环加成反应导致对异恶唑烷的顺式和反式立体异构体具有非常高的非对映选择性13- 17。有趣的是，非对映选择性是由空间因素强烈决定的，并且绝对取决于硝酮中N-烷基取代基的特性。
• Nitrones and nucleobase-containing spiro-isoxazolidines derived from isatin and indanone: solvent-free microwave-assisted stereoselective synthesis and theoretical calculations
  作者：Loredana Maiuolo、Pedro Merino、Vincenzo Algieri、Monica Nardi、Maria Luisa Di Gioia、Beatrice Russo、Ignacio Delso、Matteo Antonio Tallarida、Antonio De Nino

  DOI：10.1039/c7ra09995a

  日期：——

  because of their antiviral properties. However, in the literature few examples of synthesis of their precursors, oxindole-nitrones, are reported. In this paper, we initially present a rapid and efficient synthetic approach to ketonitrones by solvent-free microwave-assisted reaction between isatin or indanone derivatives and various hydroxylamines. The synthetic protocol is facile, clean, fast, high-yielding

  螺-羟吲哚由于其抗病毒特性而被广泛应用。然而，在文献中，很少报道合成其前体羟吲哚-硝酮的实例。在本文中，我们最初提出了一种快速，高效的合成方法，该方法通过Isatin或茚满酮衍生物与各种羟胺之间的无溶剂微波辅助反应来合成酮硝酮。合成协议简便，干净，快速，高产量且具有立体选择性。然后，我们探索了通过无溶剂的MW辅助1,3-偶极环加成合成含核苷的螺-异​​恶唑烷与靛红和茚满酮核的可能性，获得了良好的收率（74-85％），以及区域和非对映选择性。
• Synthesis of Aminocyclobutanes by Iron-Catalyzed [2+2] Cycloaddition
  作者：Florian de Nanteuil、Jérôme Waser

  DOI：10.1002/anie.201303803

  日期：2013.8.19

  Fab Four: An iron‐catalyzed [2+2] cycloaddition furnishes aminocyclobutanes with a broad range of substituents in excellent yields and diastereoselectivities. The products can be obtained on a gram scale and can be further converted to β‐peptide derivatives in a few steps. Furthermore, a [4+2] cycloaddition between an aminocyclobutane and an olefin leads to the corresponding cyclohexylamines.

  第四工厂：铁催化的[2 + 2]环加成反应可提供具有广泛取代基的氨基环丁烷，并具有出色的收率和非对映选择性。这些产物可以克量级获得，并且可以在几个步骤中进一步转化为β-肽衍生物。此外，在氨基环丁烷和烯烃之间的[4 + 2]环加成产生相应的环己胺。
• Ruthenium-catalyzed synthesis of vinylamides at low acetylene pressure
  作者：Elena Semina、Pavel Tuzina、Frank Bienewald、A. Stephen K. Hashmi、Thomas Schaub

  DOI：10.1039/d0cc01533d

  日期：——

  The reaction of cyclic amides with acetylene under low pressure, using ruthenium-phosphine catalysts, afforded a broad variety of N-vinylated amides including (azabicyclic) lactams, oxazolidinones, benzoisoxazolones, isoindolinones, quinoxalinones, oxazinanones, cyclic urea derivatives (imidazolidinones), nucleobases (thymine), amino acid anhydrides and thiazolidinone.

  使用钌膦催化剂，使环酰胺在低压下与乙炔反应，得到各种N-乙烯基化的酰胺，包括（氮杂双环）内酰胺，恶唑烷酮，苯并异恶唑酮，异吲哚啉酮，喹喔啉酮，恶唑烷酮，环脲衍生物（咪唑啉基） （胸腺嘧啶），氨基酸酸酐和噻唑烷酮。
• [EN] SYNTHESIS OF N-VINYL COMPOUNDS BY REACTING CYLIC NH-COMPOUNDS WITH ACETYLENE IN PRESENCE OF HOMOGENOUS CATALYST<br/>[FR] SYNTHÈSE DE COMPOSÉS N-VINYLIQUES PAR RÉACTION DE COMPOSÉS NH- CYLIQUES AVEC DE L'ACÉTYLÈNE EN PRÉSENCE D'UN CATALYSEUR HOMOGÈNE
  申请人：BASF SE

  公开号：WO2021122249A1

  公开（公告）日：2021-06-24

  Process to produce N-vinyl compounds by homogeneous catalysis, wherein acetylene is reacted with a cyclic compound comprising a cyclic compound having at least one nitrogen as ring member, bearing a substitutable hydrogen residue (cyclic compound C), in a liquid phase in the presence of a ruthenium complex comprising at least one phosphine as ligand (RuCat).

  通过均相催化过程生产N-乙烯基化合物，其中乙炔与至少含有一个氮作为环成员并带有可取代氢残基的环状化合物（环状化合物C）在液相中反应，并在至少含有一个磷化物作为配体的钌络合物（RuCat）的存在下进行。