1-benzyl-6-methyluracil | 33443-58-2

• 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-benzyl-6-methyluracil
• 英文别名: 1-benzyl-6-methylpyrimidine-2,4(1H,3H)-dione；1-benzyl-6-methylpyrimidine-2,4-dione
• CAS: 33443-58-2
• 化学式: C₁₂H₁₂N₂O₂
• mdl: MFCD00452852
• 分子量: 216.239
• InChiKey: LXRVJHIISSYWEJ-UHFFFAOYSA-N

物化性质

• 熔点：
  231-232 °C
• 密度：
  1.227±0.06 g/cm3(Predicted)
• 溶解度：
  19.2 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933599090

反应信息

• 作为反应物：
  描述：

  1-benzyl-6-methyluracil 在 potassium carbonate 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 1-Benzyl-3-(3-{4-[4-fluoro-2-(2,2,2-trifluoro-ethoxy)-phenyl]-piperazin-1-yl}-propyl)-6-methyl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Synthesis, pharmacology and pharmacokinetics of 3-(4-Aryl-piperazin-1-ylalkyl)-uracils as uroselective α1A-antagonists

  摘要：

  Predominance in the urethra and prostate of the alpha(1A)-adrenoceptor subtype, which is believed to be the receptor mediating noradrenaline induced smooth muscle contraction in these tissues, led to the preparation of alpha(1A)-selective antagonists to be tested as uroselective compounds for the treatment of benign prostatic hyperplasia. Thus, a number of selective alpha(1A)-adrenoceptor antagonists were synthesized and assayed in vitro for potency and selectivity. Dog pharmacokinetic parameters of 12 (RO700004) and its metabolite 40 (RO1104253) were established. The relative selectivity of intravenously administered 12, 40 and standard prazosin to inhibit hypogastric nerve stimulation-induced increases in intraurethral prostatic pressure versus phenylephrine-induced increases in diastolic blood pressure in anesthetized dogs was 76, 71 and 0.6, respectively. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00305-6
• 作为产物：
  描述：

  6-甲基尿嘧啶 在 吡啶 、 ammonium hydroxide 、 potassium carbonate 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 48.08h， 生成 1-benzyl-6-methyluracil
  参考文献：
  名称：

  Selective N1-Alkylation of 1,3-Dibenzoyluracils: One-Pot Way to N1-Monosubstituted Uracil Derivatives

  摘要：

  A new method for synthesis of N(-)(1)monosubstituted uracils and 5- and 6-methyluracil derivatives was developed. It consists in the selective N-1-deprotection of N-1,N-3-dibenzoyluracils in anhydrous dimethylformamide in the presence of potassium carbonate at room temperature and subsequent N-1-alkylation by allyl, benzyl or phenacyl type halides or by primary alcohols toluenesulfonates conducted one pot without isolation of the intermediates. Final N-3-debenzoylation by aqueous-alcoholic solution of ammonia affords the corresponding N-1-monosubstituted uracil derivatives with overall yields of 52-84%.

  DOI：

  10.3987/com-17-13696

文献信息

• [EN] FLUORINATED LYSYL OXIDASE-LIKE 2 INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS FLUORÉS DE LA LYSYL OXYDASE-LIKE 2 ET UTILISATIONS DESDITS INHIBITEURS
  申请人：PHARMAKEA INC

  公开号：WO2016144703A1

  公开（公告）日：2016-09-15

  Described herein are compounds that are LOXL2 inhibitors, methods of making such compounds, pharmaceutical compositions and medicaments comprising such compounds, and methods of using such compounds in the treatment of conditions, diseases, or disorders associated with LOXL2 activity.

  本文描述的是一种LOXL2抑制剂化合物，制备这种化合物的方法，包含这种化合物的药物组合物和药物，以及使用这种化合物治疗与LOXL2活性相关的疾病、病症或疾病的方法。
• A Convenient Approach to meso-Uracil–4,4-Difluoro-4-bora-3a, 4a-diaza-s-indacene Derivatives
  作者：M. Cordaro、M. Trapani、M. A. Castriciano、J. A. A. W. Elemans、A. Nicosia、P. Mineo

  DOI：10.1055/a-1545-7086

  日期：2021.10

  4a-diaza-s-indacene (BODIPY). In this way, regioselectively functionalized BODIPYs with a direct connection to a nucleobase were prepared in yields of 30–45%. MALDI-TOF mass spectrometry, NMR, UV/vis absorption, and steady-state and time-­resolved fluorescence spectroscopies were used to characterize the structures and the spectroscopic/photophysical properties of the resultant dyes.

  已开发出一种有效且方便的合成 1-取代尿嘧啶-6-甲醛衍生物的方案。三步序列允许使用低成本前体大量制备在 N-1 处具有各种取代基的尿嘧啶-6-甲醛。醛官能化尿嘧啶用作制备 4,4-二氟-4-bora-3a,4a-二氮杂-s-茚(BODIPY) 的内消旋-(1-取代的6-尿嘧啶)-衍生物的有用前体。通过这种方式，以 30-45% 的产率制备了与核碱基直接连接的区域选择性功能化 BODIPY。MALDI-TOF 质谱、核磁共振、紫外/可见吸收以及稳态和时间分辨荧光光谱用于表征所得染料的结构和光谱/光物理特性。
• Studies on ketene and its derivatives. CII. Reaction of diketene with cyanamide derivatives.
  作者：TETSUZO KATO、TAKUO CHIBA、TAKESHI SHIMIZU、HITOSHI TAKAHASHI

  DOI：10.1248/cpb.29.862

  日期：——

  The reaction of diketene with cyanamide gave 2-amino-6-methyl-4H-1, 3-oxazin-4-one, which was transformed to 6-methyluracil by refluxing it in acetic acid. Diketene also reacted with monosubstituted cyanamides to give 1, 3-oxazin-4-one derivatives, which could be similarly converted into 1-substituted 6-methyluracils. The reaction of diketene with dicyanodiamide afforded 2-guanidino-6-methyl-4H-1, 3-oxazin-4-one, which, on treatment with ammonia, afforded 2-guanidino-4-hydroxy-6-methylpyrimidine.

  二烯酮与氰胺的反应生成了2-氨基-6-甲基-4H-1,3-氧杂嗪-4-酮，通过在醋酸中回流处理可转化为6-甲基尿嘧啶。二烯酮还与单取代氰胺反应生成1,3-氧杂嗪-4-酮衍生物，这些衍生物也可类似地转化为1-取代的6-甲基尿嘧啶。二烯酮与双氰氨的反应生成了2-氨基-6-甲基-4H-1,3-氧杂嗪-4-酮，随后用氨处理可得到2-氨基-4-羟基-6-甲基嘧啶。
• A new synthesis of 1,3-thiazines and their transformation into 1-substituted-6-alkyluracils by extrusion of carbonyl sulfide
  作者：Valera N. Yuskovets、Boris A. Ivin

  DOI：10.1016/s0040-4039(03)01262-0

  日期：2003.7

  A simple synthesis of 5-acyl-4-hydroxy-3,6-dihydro-2H-1,3-thiazine-2,6-diones from malonic acid, potassium thiocyanate and acid anhydrides is described. A new, general, regioselective method for the synthesis of 1-substituted-6-alkyluracils by the reaction of these thiazines with primary alkyl and arylamines is reported.

  描述了由丙二酸，硫氰酸钾和酸酐简单合成5-酰基-4-羟基-3,6-二氢-2 H -1,3-噻嗪-2,6-二酮。据报道，通过这些噻嗪与伯烷基和芳基胺的反应合成1-取代的6-烷基尿嘧啶的一种新的，通用的区域选择性方法。
• Azines and Azoles: CXXII. New Regioselective Synthesis of 1-Substituted 6-Alkyluracils
  作者：V. N. Yuskovets、A. V. Moskvin、L. E. Mikhailov、B. A. Ivin

  DOI：10.1007/s11176-005-0185-2

  日期：2005.1

  Readily available 5-acyl-4-hydroxy-3,6-dihydro-2H-1,3-thiazine-2,6-diones with primary alkyl- and arylamines in mild conditions (boiling in propan-2-ol) to give Schiff bases. In more rigid conditions (boiling in DMF), the reaction is accompanied by COS liberation and provides 1-substituted 6-alkyluracils. This previously unknown reaction possesses a considerable synthetic potential and can be considered as a new, general, and regioselective synthetic approach to 1-substituted 6-alkyluracils.

  现成的 5-酰基-4-羟基-3,6-二氢-2H-1,3-噻嗪-2,6-二酮与伯烷基和芳基胺在温和条件下（在丙-2-醇中沸腾）反应生成希夫碱。在更严格的条件下（在 DMF 中沸腾），反应伴随着 COS 的释放，生成 1-取代的 6-烷基尿嘧啶。这一之前未知的反应具有相当大的合成潜力，可被视为 1-取代的 6-烷基尿嘧啶的一种新的、通用和区域选择性合成方法。