1-allyl-6-methyluracil | 114066-90-9

• 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-allyl-6-methyluracil
• 英文别名: 1-allyl-6-methyl-1H-pyrimidine-2,4-dione；1-Allyl-6-methyl-1H-pyrimidin-2,4-dion；6-Methyl-1-(prop-2-en-1-yl)pyrimidine-2,4(1H,3H)-dione；6-methyl-1-prop-2-enylpyrimidine-2,4-dione
• CAS: 114066-90-9
• 化学式: C₈H₁₀N₂O₂
• 分子量: 166.18
• InChiKey: GYXFJRBGWKHEEH-UHFFFAOYSA-N

物化性质

• 熔点：
  174-175 °C(Solv: ethanol (64-17-5); 1-butanol (71-36-3))
• 密度：
  1.130±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 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-allyl-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

• 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。
• Synthesis and biological activity of 1,3-di(3-dimethoxyphosphorylpropyl) derivatives of uracil and 6-methyluracil
  作者：G. B. Kovalev、A. I. Rakhimov、A. A. Ozerov、V. I. Petrov、A. A. Spasov、P. M. Vasil'ev、S. G. Kovalev、M. S. Novikov、A. B. Rozenblit、V. E. Golender、A. M. Kofman

  DOI：10.1007/bf00765788

  日期：1990.6

  encountered in nature as part of heterocyclic compounds. It is included in DNA and RNA in the form of nucleotides. Many uracil derivatives exhibit a high level of biological activity. The alkylated and acylated derivatives of 5-fluorouracil, for example, l-(2-tetrahydrofuryl)-5-fluorouracil [2], is widely used for the chemotherapy of malignant tumors. Derivatives of pyrimidine nucleosides and nucleotides are

  尿嘧啶片段在自然界中经常作为杂环化合物的一部分出现。它以核苷酸的形式包含在 DNA 和 RNA 中。许多尿嘧啶衍生物表现出高水平的生物活性。5-氟尿嘧啶的烷基化和酰化衍生物，如l-(2-四氢呋喃基)-5-氟尿嘧啶[2]，广泛用于恶性肿瘤的化疗。嘧啶核苷和核苷酸的衍生物用作抗病毒制剂[ii]。
• Potentiating effects of N1,N3-diallyluracil, N1,N3-diallylthymine and N1,N3-diallyl-6-methyluracil on pentobarbital-induced sleep and diazepam-induced motor incoordination.
  作者：YUJI TATEOKA、TOSHIYUKI KIMURA、KAZUHITO WATANABE、IKUO YAMAMOTO、ING KANG HO

  DOI：10.1248/cpb.35.4928

  日期：——

  N-Allyl derivatives of uracil (U), thymine (T) and 6-methyluracil (6-MU) were prepared, and their pharmacological activities (hypnotic activity and anticonvulsant activity against pentylenetetrazol (PTZ) -induced seizures) and interactions with three sedative-hypnotics [pentobarbital (PB), barbital (B) and diazepam (DZ)] were investigated in mice. N1, N3-Diallyluracil (DAU) alone exhibited hypnotic and anticonvulsant activities. None of the other allyl derivatives showed both pharmacological activities. As regards interactions, most of the compounds tested prolonged PB-induced sleep at either 80 or 160 mg/kg, i.p. Further, U, T, and 6-MU (160 mg/kg, i.p.) also prolonged the PB-induced sleeping time. DAU showed a prolonging effect on PB-induced sleep when given by intracerebroventricular (i.c.v.) injection. DAU, N1, N3-diallylthymine (DAT) and N1-monoallyluracil (N1-MAU) significantly prolonged the B-induced sleeping time at a dose of 160 mg/kg, i.p. Further, DAU and DAT (40 mg/kg, i.p.) enhanced DZ-induced motor incoordination. These results indicate that U and related compounds possess central nervous system (CNS) - depressant effects and DAU is the most potent among the N-allyl derivatives tested.

  制备了尿嘧啶（U）、胸腺嘧啶（T）和6-甲基尿嘧啶（6-MU）的N-烯丙基衍生物，及其药理活性（对戊四氮（PTZ）引起的癫痫发作的催眠活性和抗惊厥活性）以及与三种镇静剂的相互作用- 在小鼠身上研究了安眠药[戊巴比妥（PB）、巴比妥（B）和地西泮（DZ）]。 N1、N3-二烯丙基尿嘧啶（DAU）单独表现出催眠和抗惊厥活性。其他烯丙基衍生物均未表现出这两种药理活性。至于相互作用，大多数化合物在 80 或 160 mg/kg（腹膜内注射）下测试了 PB 诱导的睡眠延长。此外，U、T 和 6-MU（160 mg/kg，腹腔注射）也延长了 PB 诱导的睡眠时间。当通过脑室内 (i.c.v.) 注射时，DAU 对 PB 诱导的睡眠有延长作用。 DAU、N1、N3-二烯丙基胸腺嘧啶 (DAT) 和 N1-单烯丙基尿嘧啶 (N1-MAU) 在腹腔注射 160 mg/kg 的剂量下显着延长 B 诱导的睡眠时间。此外，DAU 和 DAT（40 mg/kg，腹腔注射）增强了 DZ 引起的运动不协调。这些结果表明 U 和相关化合物具有中枢神经系统 (CNS) 抑制作用，并且 DAU 是测试的 N-烯丙基衍生物中最有效的。
• Synthesis and Antiviral Activity of Acyclic Nucleoside Analogues of 6-Methyluracil and 4-Alkylamino-6-methyl-2(1H)-pyrimidinones
  作者：Sunita Bhat

  DOI：10.1135/cccc19940683

  日期：——

  Reaction of 2,4-Dimethoxy-6-methylpyrimidine (I) with allyl bromide or benzyl bromide afforded 1-substituted 4-methoxy-6-methyl-2(1H)-pyrimidinone intermediates III, X. Oxidation of the compound III afforded racemic cis diol VI. O-Demethylation and nucleophilic displacement of the intermediates III, VI and X gave 1-substituted 6-methyluracils IV, VII, IX and 1-substituted 4-alkylamino-6-methyl-2(1H)-pyrimidinones V, VIII, XII in good yields. The compounds II - XII were evaluated against Ranikhet disease virus (RDV); compounds Vb, VII, X, XIIb - XIId showed 100, 43, 44, 75, 72 and 100% inhibition, respectively.

  2,4-二甲氧基-6-甲基嘧啶（I）与烯丙基溴或苄基溴的反应得到了1-取代的4-甲氧基-6-甲基-2（1H）-嘧啶酮中间体III，X。化合物III的氧化产物是外消旋的顺式二醇VI。III、VI和X的脱甲基和亲核置换反应产生了1-取代的6-甲基尿嘧啶IV、VII、IX和1-取代的4-烷基氨基-6-甲基-2（1H）-嘧啶酮V、VIII、XII，收率良好。化合物II-XII对拉尼克特病毒（RDV）进行了评价，其中化合物Vb、VII、X、XIIb-XIId分别显示出100％、43％、44％、75％、72％和100％的抑制率。
• Behrend; Bueckendorff, Justus Liebigs Annalen der Chemie, 1911, vol. 385, p. 316
  作者：Behrend、Bueckendorff

  DOI：——

  日期：——