1-n-butyluracil | 705-06-6

• 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-n-butyluracil
• 英文别名: N¹-butyluracil；n-butyl uracil；1-butyluracil；1-butyl-1H-pyrimidine-2,4-dione；N-butylthymine；1-Butylpyrimidine-2,4(1h,3h)-dione；1-butylpyrimidine-2,4-dione
• CAS: 705-06-6
• 化学式: C₈H₁₂N₂O₂
• 分子量: 168.195
• InChiKey: MUEKJTHBUFFNQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险性防范说明：
  P264,P280,P302+P352,P305+P351+P338,P332+P313,P337+P313,P362
• 危险性描述：
  H315,H319
• 储存条件：
  2-8°C，干燥

反应信息

• 作为反应物：
  描述：

  1-n-butyluracil 在 吡啶 、 正丁基锂 、 一氯化碘 、 甲胺 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 乙腈 为溶剂， 反应 52.5h， 生成
  参考文献：
  名称：

  具有尿嘧啶氢键功能的乙二硫基四硫富瓦烯衍生物的二维网络及其四乙胺基喹啉甲烷配合物的通道结构

  摘要：

  设计并合成具有N 1-丁基尿嘧啶或N 1-苯基尿嘧啶部分的乙二硫四硫富富烯烯（EDT-TTF）衍生物，作为新的氢键电子给体分子，目的是将多个S···S相互作用引入所组成的氢键结构中TTF-nucleobase系统的。在EDT-TTF衍生物的晶体中，通过π··π，多个S···S相互作用和互补的双氢键形成二维片层结构。在具有分离柱的EDT-TTF- N 1-丁基尿嘧啶二聚体的四氰基喹二甲烷（TCNQ）电荷转移复合物中，电子供体分子的层结构是通过非共价相互作用而构建的。这尿嘧啶部分的正丁基用于分隔供体层之间的空间，从而形成通道结构。无序的TCNQ分子位于通道的微孔空间中。TCNQ复合物在单晶中表现出高电导率（σrt = 2.1 S cm - 1）。

  DOI：

  10.1021/jo060748l
• 作为产物：
  描述：

  3,3-二乙氧基丙酰胺 、 异氰酸正丁酯 在 硫酸 作用下， 以 甲苯 、 乙醇 、 水 为溶剂， 反应 22.67h， 以49%的产率得到1-n-butyluracil
  参考文献：
  名称：

  Hydrogen-Bonded Charge-Transfer Complexes of TTF Containing a Uracil Moiety:  Crystal Structures and Electronic Properties of the Hydrogen Cyananilate and TCNQ Complexes

  摘要：

  [GRAPHICS]A novel TTF-based donor with a uracil moiety, TTF-(1-n-butyluracil-5-yl) (TnbU), was synthesized. Crystal structures of both TnbU and the charge-transfer complex of TnbU-hydrogen cyananilate possess complementary double hydrogen bonds through uracil moieties and pi-stacking dimer structures between TTF skeletons. Furthermore, the TnbU-TCNQ charge-transfer complex shows a high electrical conductivity underlying the partial charge-transfer accompanied by a hydrogen-bonding interaction, which was substantiated in terms of the measurements of the IR, electronic spectra, and conductivity.

  DOI：

  10.1021/ol020081z

文献信息

• Highly efficient protocol for one-pot N-alkylation of nucleobases using alcohols in bmim[Br]: a rapid route to access acyclic nucleosides
  作者：Mohammad Navid Soltani Rad、Somayeh Behrouz、Elham Zarenezhad、Narjes Kaviani

  DOI：10.1007/s13738-015-0633-9

  日期：2015.9

  Highly efficient protocol for one-pot N-alkylation of nucleobases using alcohol in ionic liquid media as a straightforward route to access acyclic nucleoside was described. In this protocol purine, pyrimidine as well as azole derivatives underwent the N-alkylation reaction with primary or secondary alcohols using TsCl/TEA/K2CO3 in bmim[Br] to afford the products in good-to-excellent yields. The influence of factors in this method including the type of ionic liquid, base and sulfonating agents was discussed. The current method showed an appropriate selectivity in reaction with primary alcohols in comparison with secondary alcohols. This protocol is mild, safe and easy to apply; moreover, it is quite compatible with eco-friendly and green chemistry protocols, since the exploitation of toxic and hazardous materials such as DMF and alkyl halides has been prevented.

  描述了一种在离子液体介质中使用醇对核苷碱基进行高效一锅法N-烷基化的协议，作为获取无环核苷的直接途径。在此协议中，嘌呤、嘧啶以及唑类衍生物与一级或二级醇在TsCl/TEA/K2CO3于bmim[Br]中进行N-烷基化反应，得到良好至极佳产率的产物。讨论了该方法中包括离子液类型、碱和磺化剂等因素的影响。当前方法在反应中对一级醇显示出适当的优先选择性，相较于二级醇。该协议温和、安全且易于应用；此外，由于避免了使用如DMF和烷基卤等有毒及危险材料，它与生态友好和绿色化学协议高度兼容。
• [EN] SMALL MOLECULES AGAINST CEREBLON TO ENHANCE EFFECTOR T CELL FUNCTION<br/>[FR] PETITES MOLÉCULES DIRIGÉES CONTRE LE CÉRÉBLON POUR AMÉLIORER LA FONCTION DES LYMPHOCYTES T EFFECTEURS
  申请人：H LEE MOFFITT CANCER CENTER & RES INST INC

  公开号：WO2017161119A1

  公开（公告）日：2017-09-21

  Disclosed are small molecules against cereblon to enhance effector T cell function. Methodos of making thes molecules and methods of using them to treat various disease states are also disclosed.

  披露了针对小脑蛋白以增强效应T细胞功能的小分子。还披露了制造这些分子的方法以及使用它们治疗各种疾病状态的方法。
• Protons as the Triggers to Regulate Hydrogen-Bonding Receptors
  作者：Mohammad H. Al-Sayah、Neil R. Branda

  DOI：10.1021/ol0170915

  日期：2002.3.1

  [reaction: see text] The protonation of alkylamines in two novel receptors results in intramolecular host-guest associations between the resulting ammonium ions and crown ether macrocycles. These interactions result in conformational changes of the receptors and prevent them from acting as hydrogen bond complements for uracil and carboxylate guest species.

  [反应：见正文]两个新受体中烷基胺的质子化导致所得铵离子与冠醚大环之间的分子内主客体缔合。这些相互作用导致受体的构象变化，并阻止它们充当尿嘧啶和羧酸盐客体物种的氢键补体。
• Water-induced gel formation of an oleanlic acid–adenine conjugate and the effects of uracil derivative on the gel stability
  作者：Jinrong Lu、Jun Hu、Chulong Liu、Hongxin Gao、Yong Ju

  DOI：10.1039/c2sm26085a

  日期：——

  The conjugate of oleanlic acid with adenine was synthesized and it could be gelled in mixed solvents of THF and water, but no gel was formed in the single organic solvent. The self-aggregation behaviour and physical properties of the organogel were characterized by 1H NMR, FT-IR, and scanning electron microscopy. The morphology and the stability of the gel were remarkably affected by the uracil derivative through destroying hydrogen-bonding.

  将oleanlic酸与腺苷结合合成，该化合物可以在四氢呋喃和水混合溶剂中形成凝胶，但在单一有机溶剂中没有形成凝胶。通过1H NMR、傅里叶变换红外光谱和扫描电子显微镜对有机凝胶的自组装行为和物理性质进行了表征。尿嘧啶衍生物通过破坏氢键对凝胶的形态和稳定性产生了显著影响。
• Improved One-Step Procedure for the Preparation of 1-Substituted and 1,3-Disubstituted Uracils and 2-Thiouracils
  作者：Ib Winckelmann、Erik H. Larsen

  DOI：10.1055/s-1986-31867

  日期：——

  A convenient one-pot procedure for the synthesis of 1-substituted and 1,3- disubstituted uracils and 2-thiouracils consists of acylation of ureas, or thioureas with methyl 3,3-dimethoxypropanoate in the presence of a strong base, and acidic work-up. The yields range from 36 to 99%. In all cases, only one regioisomer is isolated.

  合成 1-取代和 1,3-二取代尿嘧啶和 2-硫尿嘧啶的简便一步法包括在强碱存在下用 3,3-二甲氧基丙酸甲酯酰化脲类或硫脲类化合物，然后进行酸性处理。产率从 36% 到 99%不等。 在所有情况下，只能分离出一种 Regioisomer。