3-N-allyl-6-methyl-2-thiouracil | 60478-14-0

• 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: 3-N-allyl-6-methyl-2-thiouracil
• 英文别名: 3-allyl-6-methyl-2-thiouracil；3-allyl-6-methyl-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one；3-Allyl-6-methyl-2-thioxo-2,3-dihydro-1H-pyrimidin-4-on；6-methyl-3-prop-2-enyl-2-sulfanylidene-1H-pyrimidin-4-one
• CAS: 60478-14-0
• 化学式: C₈H₁₀N₂OS
• 分子量: 182.246
• InChiKey: AXULPMJUAHSRPI-UHFFFAOYSA-N

物化性质

• 熔点：
  189 °C
• 沸点：
  264.2±33.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 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：
  64.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-N-allyl-6-methyl-2-thiouracil 在 碘 作用下， 生成 2-iodomethyl-7-methyl-2,3-dihydrothiazolo[3,2-a]pyrimidin-5-one
  参考文献：
  名称：

  Ajello; Miraglia, Gazzetta Chimica Italiana, 1948, vol. 78, p. 921,929

  摘要：

  DOI：
• 作为产物：
  描述：

  1-allyl-6-methyl-2-thiouracil 在 二(氰基苯)二氯化钯 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 3-N-allyl-6-methyl-2-thiouracil
  参考文献：
  名称：

  Palladium-catalyzed polyhetero-Claisen rearrangement of 2-(allylthio)pyrimidin-4(3H)-ones

  摘要：

  DOI：

  10.1021/jo00206a007

文献信息

• A facile synthesis of the novel thiazolo[3,2-a]pyrimidine derivatives
  作者：Renata Studzińska、Marcin Wróblewski、Aleksandra Karczmarska-Wódzka、Renata Kołodziejska

  DOI：10.1016/j.tetlet.2014.01.033

  日期：2014.2

  2-iodomethyl-2,3-dihydrothiazolo[3,2-a]pyrimidin-5-ones are prepared via the reaction of 3-allyl-2-thiouracil derivatives with bromine or iodine chloride, respectively. The 6-bromo and 6-nitro derivatives are synthesized by an electrophilic substitution at C-6 of the thiazolopyrimidine system. As a result, novel 2,3-dihydrothiazolo[3,2-a]pyrimidin-5-one derivatives are obtained. Hydrogen halide elimination

  通过3-烯丙基-2-硫尿嘧啶衍生物分别与溴或氯化碘反应，制得2-溴甲基-和2-碘甲基-2,3-二氢噻唑并[3,2- a ]嘧啶-5-酮。通过噻唑并嘧啶系统的C-6处的亲电取代合成6-溴和6-硝基衍生物。结果，获得了新的2，3-二氢噻唑并[3，2 - a ]嘧啶-5-酮衍生物。还报道了从2-卤甲基-2，3-二氢噻唑并[3，2 - a ]嘧啶-5-酮中消除卤化氢。
• Synthesis and Sedative-Hypnotic Effects of N3-Allyl- and N1-Allyl-5,6-substituted 2-Thiouracil Derivatives in Mice.
  作者：Marcin DRAMINSKI、Krzysztof TURSKI、Yuji TATEOKA、Toshiyuki KIMURA、Kazuhito WATANABE、Shigemi KONDO、Ing Kang HO、Ikuo YAMAMOTO

  DOI：10.1248/cpb.46.1370

  日期：——

  Twenty four thiouracil derivatives, including N3-allyl- (19) and N1-allyl-2-thiouracil (20) were synthesized and their pharmacological effects [sedative-hypnotic activity (loss of righting reflex and spontaneous activity), convulsant activity, effect on pentobarbital (PB)-induced sleep and mortality] were evaluated in mice at doses of 320 mg/kg, i.p. and 2 μmol/mouse by intracerebroventricular (i.c.v.) injections, respectively. N3-Allyl-6-propyl-2-thiouracil (3), N3-allyl-5, 6-dimethyl-2-thiouracil (10), N3-allyl-1, 2, 3, 4, 5, 6, 7, 8, 9-nonahydro-4-oxo-2-thiocyclohepta[d]pyrimidine (16) and N3-allyl-5-methyl-2-thiouracil (18) exhibited sedative-hypnotic activity, whereas N3-allyl-6-ethyl-5-methyl-2-thiouracil (11), N1-allyl-5-methyl-2-thiouracil (21), N1-allyl-1, 2, 3, 4, 5, 6, 7, 8, 9-nonahydro-4-oxo-2-thiocyclohepta[d]pyrimidine (23) and N1-allyl-5, 6-dimethyl-2-thiouracil (24) conversely displayed clonic- and/or tonic-convulsant seizures. N3-Allyl-6-propyl-2-thiouracil (3) and N3-allyl-5-methyl-2-thiouracil (18) decreased spontaneous activity. Other compounds examined were inactive, or only slightly active in the sedative-hypnotic assay even at high doses. Fifteen compounds (1-4, 7, 10, 11, 14-16, 18-21, and 23) significantly prolonged the PB-induced sleeping time. Interestingly, only N1-allyl-5, 6-dimethyl-2-thiouracil (24) shortened the PB-induced sleeping time. These results showed that these thiouracils possessed many different effects such as sedative-hypnotic, anticonvulsant and/or convulsant, and that N3-allyl-5-methly-2-thiouracil (18) and N1-allyl-5, 6-dimethyl-2-thiouracil (24) had the most potent hypnotic activity and antagonistic effect against PB, respectively.

  合成了 24 种硫脲嘧啶衍生物，包括 N3-allyl- (19) 和 N1-allyl-2-thiouracil (20)，并分别以 320 毫克/千克和 2 微摩尔/只小鼠的剂量在小鼠体内进行脑静脉注射，评估了它们的药理作用[镇静催眠活性（丧失直立反射和自发活动）、惊厥活性、对戊巴比妥（PB）诱导的睡眠和死亡率的影响]。p.和 2 μmol/只小鼠进行脑室内注射（i.c.v.）。N3-烯丙基-6-丙基-2-硫脲嘧啶（3）、N3-烯丙基-5，6-二甲基-2-硫脲嘧啶（10）、N3-烯丙基-1，2，3，4，5，6，7，8，9-壬氢-4-氧代-2-硫环庚基[d]嘧啶（16）和 N3-烯丙基-5-甲基-2-硫脲嘧啶（18）具有镇静催眠活性、而 N3-烯丙基-6-乙基-5-甲基-2-硫脲嘧啶（11）、N1-烯丙基-5-甲基-2-硫脲嘧啶（21）、N1-烯丙基-1、2、3、4、5、6、7、8、9-壬氢-4-氧代-2-硫代环庚基[d]嘧啶（23）和 N1-烯丙基-5，6-二甲基-2-硫脲嘧啶（24）则相反，表现出阵挛性和/或强直性惊厥发作。N3-烯丙基-6-丙基-2-硫脲嘧啶（3）和 N3-烯丙基-5-甲基-2-硫脲嘧啶（18）降低了自发活动。其他受试化合物在镇静催眠试验中没有活性，或即使在高剂量下也只有轻微活性。有 15 种化合物（1-4、7、10、11、14-16、18-21 和 23）明显延长了 PB 诱导的睡眠时间。有趣的是，只有 N1-烯丙基-5，6-二甲基-2-硫脲嘧啶（24）缩短了 PB 诱导的睡眠时间。这些结果表明，这些硫脲嘧啶具有多种不同的作用，如镇静催眠、抗惊厥和/或惊厥，而 N3-烯丙基-5-甲硫基-2-硫脲嘧啶（18）和 N1-烯丙基-5，6-二甲基-2-硫脲嘧啶（24）分别具有最强的催眠活性和对 PB 的拮抗作用。
• Reaction of 3-Allyl-6-methyl-2-thiouracil with Bromine and Iodine
  作者：D. G. Kim、T. V. Frolova、K. Yu. Petrova、V. V. Sharutin

  DOI：10.1134/s1070363219050074

  日期：2019.5

  3-Allyl-6-methyl-2-thiouracil reacts with iodine to form 2-iodomethyl-7-methyl-5-oxo-3,5-dihydro-2H-thiazolo-[3,2-a]pyrirmdinium iodide. The reaction with bromine leads to the formation of a mixture of 2-bromomethyl-7-methyl-5-oxo-3,5-dihydro-2H-thiazolo[3,2-a]pyrimidinium and 6-bromo-2-bromomethyl-7-memyl-5-oxo-3,5-dihydro-2H-thiazolo[3,2-a]pyrimidinium bromides.

  3-烯丙基-6-甲基-2-硫尿嘧啶与碘反应形成2-碘甲基-7-甲基-5-氧代-3,5-二氢-2 H-噻唑基-[3,2- a ]碘化吡啶鎓。与溴的反应导致形成2-溴甲基-7-甲基-5-氧代-3,5-二氢-2 H-噻唑并[3,2- a ]嘧啶鎓和6-溴-2-溴甲基的混合物-7-甲基-5-氧代-3，5-二氢-2 H-噻唑并[3，2- a ]嘧啶溴化物。
• Desulfitative Cross-Coupling of Protecting Group-Free 2-Thiouracil Derivatives with Organostannanes
  作者：Qi Sun、Franck Suzenet、Gérald Guillaumet

  DOI：10.1021/jo1003482

  日期：2010.5.21

  We here report a unique and efficient copper bromide mediated pallado-catalyzed coupling of protecting group-free 2-thiouracil derivatives with organostannanes. The nature of the copper appears to be crucial for successful cross coupling.
• Synthesis of New Thiazolo[3,2-a]pyrimidin-5-one Derivatives in Reaction of 3-Allyl-2-thiouracils Cyclization
  作者：Renata Studzinska、Marcin Wr傭lewski、Marcin Draminski

  DOI：10.3987/com-08-11365

  日期：——

  The series of thiazolo[3,2-a]pyrimidin-5-one derivatives in cyclization reaction of 3-allyl-2-thiouracil derivatives with iodine monochloride, and then hydrogen iodide elimination from intermediate reaction product has been obtained. On the basis of the studies of reaction kinetics, the elimination reaction mechanism has been proposed. Moreover, the influence of substituent on the reaction elimination rate has been investigated.