2,4,6-tris(trimethylsilyloxy)pyrimidine | 31111-39-4

• 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: 2,4,6-tris(trimethylsilyloxy)pyrimidine
• 英文别名: 2,4,6-tris(trimethylsiloxy)pyrimidine；Pyrimidine, 2,4,6-tris(trimethylsiloxy)-；[2,6-bis(trimethylsilyloxy)pyrimidin-4-yl]oxy-trimethylsilane
• CAS: 31111-39-4
• 化学式: C₁₃H₂₈N₂O₃Si₃
• 分子量: 344.633
• InChiKey: MTDRSUCYKPIFHV-UHFFFAOYSA-N

物化性质

• 沸点：
  144-145 °C(Press: 13 Torr)
• 密度：
  0.973±0.06 g/cm3(Predicted)
• 保留指数：
  1600;1592

计算性质

• 辛醇/水分配系数(LogP)：
  4.12
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  53.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  氯甲基二甲基氯硅烷 、 2,4,6-tris(trimethylsilyloxy)pyrimidine 以 乙腈 为溶剂， 反应 3.0h， 以95%的产率得到6-[(chlorodimethylsilyl)methyl]-2,2-dimethyl-2H-[1,4,2]-oxazasilolo[4,5-c]pyrimidine-5,7(3H,6H)-dione
  参考文献：
  名称：

  尿嘧啶，巴比妥酸和5,5-二甲基巴比妥酸的双核硅配合物：环状低聚物的水解形成（1）†

  摘要：

  描述了通过与（氯甲基）二甲基氯硅烷和（氯甲基）二氯（甲基）硅烷反应，衍生自尿嘧啶，巴比妥酸和5,5-二甲基巴比妥酸的双核硅配合物的合成和性质。在所有三组化合物中，氧原子均与硅弱配位。双核化合物的轻度水解会导致形成环状低聚物，每个环状低聚物具有2-9个单体单元，其中各个单元通过硅氧烷基团连接。氯化锂被证明是有效的模板，将低聚限制为二聚体并防止形成更高质量的产物。

  DOI：

  10.1021/om100461b
• 作为产物：
  描述：

  巴比妥酸 生成 2,4,6-tris(trimethylsilyloxy)pyrimidine
  参考文献：
  名称：

  FOLKERS, GERD;JUNGINGER, GERLINDE;MULLER, CHRISTA E.;SCHLOZ, ULRICH;EGER,+, ARCH. PHARM., 322,(1988) N, C. 119-123

  摘要：

  DOI：

文献信息

• Synthese computergraphik berechneter high-anti-fixierter Pyrimidin-Nucleosid-Analoga mit potentieller virostatischer und antineoplastischer Wirksamkeit
  作者：Gerd Folkers、Gerlinde Junginger、Christa E. Müller、Ulrich Schloz、Kurt Eger

  DOI：10.1002/ardp.19893220213

  日期：——

  substituierte 6,2′‐Anhydrouridine 5a–e dargestellt. Durch die aus der 6,2′‐Verknüpfung resultierende N1, C1‐Fixierung des Zuckerrestes an die Nucleobase in der high‐anti‐Konformation sollten Substanzen mit antiviralen und antineoplastischen Wirkungen zu erhalten sein. In Zellkulturtestsystemen waren die vermuteten Wirkungen jedoch bisher nicht nachweisbar.

  基于单取代的呋喃核糖基巴比妥酸衍生物 4a-e，其中一些尚未被描述，制备了 C-5 取代的新型 6,2'-脱水尿苷 5a-e。糖残基的 N1、C1 固定在由 6,2' 键产生的高反构象的核碱基上，应提供具有抗病毒和抗肿瘤作用的物质。然而，在细胞培养测试系统中尚未检测到可疑的影响。
• Tuning Exciton Coupling of Merocyanine Nucleoside Dimers by RNA, DNA and GNA Double Helix Conformations
  作者：Julia Dietzsch、David Bialas、Johannes Bandorf、Frank Würthner、Claudia Höbartner

  DOI：10.1002/anie.202116783

  日期：2022.2.21

  The barbituric acid merocyanine (BAM) is reported as a nucleobase surrogate that forms hydrogen-bonded base pairs, and antiparallel as well as rotationally stacked dimer aggregates, with orientation- and conformation-sensitive exciton coupling strength.

  据报道，巴比妥酸部花青（BAM）是一种核碱基替代物，可形成氢键碱基对、反平行以及旋转堆叠的二聚体聚集体，具有方向和构象敏感的激子耦合强度。
• Azines and Azoles: CXX. Synthesis of Acyclic Analogs of N¹-Ribosides of Barbituric Acid and Its 5-ylidene Derivatives
  作者：E. P. Studentsov、A. N. Kokhanovskii、M. B. Ganina、N. I. Nikolaeva、E. V. Fedorova、A. V. Moskvin、B. A. Ivin

  DOI：10.1023/b:rugc.0000025513.88248.94

  日期：2004.2

  The reaction of 2,4,6-tris(trimethylsiloxy)pyrimidine with 2-oxabutane-1,4-diyl diacetate in methylene chloride in methylene chloride in the presence of SnCl4 proceeds regioselectively to form 1-[(2-acetoxyethoxy)methyl]barbituric acid. The latter is readily deacetylated to a free acyclic analog of N-ribosides of barbituric acid. 1[(2-Acetoxy- and 2-hydroxyethoxy)methyl]barbituric acids easily react with aromatic and heterocyclic aldehydes in water and organic solvents, forming 5-ylidenebarbituric acids. The structure of the products was proved by H-1 NMR and UV spectroscopy. Certain of the products exhibit a moderate antimicrobial and antiviral activity.
• Synthesis and Structure−Activity Relationships of Uracil Nucleotide Derivatives and Analogues as Agonists at Human P2Y₂, P2Y₄, and P2Y₆ Receptors
  作者：Ali El-Tayeb、Aidong Qi、Christa E. Müller

  DOI：10.1021/jm060848j

  日期：2006.11.30

  A series of UTP, UDP, and UMP derivatives and analogues were synthesized and evaluated at the human pyrimidinergic P2Y receptor subtypes P2Y(2), P2Y(4), and P2Y(6) stably expressed in 1321N1 astrocytoma cells. Substituents at N3 of UTP were poorly tolerated by P2Y2 and P2Y4 receptors. In contrast, a large phenacyl substituent at N3 of UDP was well tolerated by the P2Y6 receptor, yielding a potent and selective P2Y6 receptor agonist (3-phenacyl-UDP, EC50 = 70 nM, > 500-fold selective). The most potent and selective P2Y2 receptor agonist of the present series was 2-thio-UTP (EC50 = 50 nM, >= 30-fold selective vs P2Y(4) and P2Y6). All modifications at the uracil base of UTP led to a decrease in potency at the P2Y4 receptor. A beta,gamma-dichloromethylene modification in the triphosphate chain of 5-bromo-UTP was tolerated by all three receptor subtypes, thus opening up a new strategy to obtain ectonucleotide diphosphohydrolase- and phosphatase-resistant P2Y(2), P2Y(4), and P2Y(6) receptor agonists.
• Tzeng, Cherng-Chyi; Panzica, Raymond P.; Naguib, Fardos N.M., Journal of Heterocyclic Chemistry, 1993, vol. 30, # 5, p. 1399 - 1404
  作者：Tzeng, Cherng-Chyi、Panzica, Raymond P.、Naguib, Fardos N.M.、Kouni, Mahmoud H. el

  DOI：——

  日期：——

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