5-氟-6-甲基-2,4(1H,3H)-嘧啶二酮 | 1480-99-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 5-氟-6-甲基-2,4(1H,3H)-嘧啶二酮
• 英文名称: 5-Fluor-6-methyluracil
• 英文别名: 5-fluoro-6-methyl-1H-pyrimidine-2,4-dione；5-Fluoro-6-methyluracil；5-fluoro-6-methyl-1H-pyrimidine-2,4-dione
• CAS: 1480-99-5
• 化学式: C₅H₅FN₂O₂
• 分子量: 144.105
• InChiKey: HHVJAXFFVMSNFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2933599090

反应信息

• 作为反应物：
  描述：

  5-氟-6-甲基-2,4(1H,3H)-嘧啶二酮 在 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 为溶剂， 反应 11.0h， 生成 1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-5-fluoro-6-methyluracil
  参考文献：
  名称：

  尿苷的6-取代和5,6-二取代衍生物：立体选择性合成，与尿苷磷酸化酶的相互作用以及体外抗肿瘤活性。

  摘要：

  描述了通过路易斯酸催化的（a）三甲基硅烷化的6-烷基-4-烷基硫尿嘧啶与1-O-乙酰基-2,3,5-三-O-苯甲酰基-β-的缩合反应合成6-烷基尿苷的立体选择程序。 D-核呋喃糖（ABR）和（b）三甲基甲硅烷基化的6-烷基-3-苄基尿嘧啶与ABR。随后通过使用配合物BBr3-THF的新的改性方法，使用1N三氟乙酸除去4-甲硫基，并除去3-苄基。此外，通过依次用SeO 2氧化并用四丁基硼氢化铵还原6-甲基尿苷（5）获得6-（羟甲基）尿苷（39）和5-氟-6-（羟甲基）尿苷（40）。分别通过39和40的DAST处理，获得了5-氟-6-甲基尿苷和3-氟-6-甲基尿苷（35），以及它们相应的6-氟甲基同源物41和42。对于前述关于糖基键的固定顺式构象的所有核苷，1 H NMR光谱进一步证实戊糖环主要存在于构象N（3'-内）。大多数核苷是大肠杆菌嘧啶核苷磷酸化酶的弱底物。其中两个39和41具有6-C

  DOI：

  10.1021/jm950675q
• 作为产物：
  描述：

  6-甲基尿嘧啶 在 Selectfluor 作用下， 以 水 为溶剂， 反应 4.0h， 以37%的产率得到5-氟-6-甲基-2,4(1H,3H)-嘧啶二酮
  参考文献：
  名称：

  Eco-friendly fluorination of 6-methyl- and 1,3,6-trimethyluracils in water

  摘要：

  DOI：

  10.1134/s1070428014070252

文献信息

• Promotional effect of ionic liquids in electrophilic fluorination of methylated uracils
  作者：Gennady I. Borodkin、Innokenty R. Elanov、Yury V. Gatilov、Vyacheslav G. Shubin

  DOI：10.1039/c6ra10850d

  日期：——

  A novel efficient protocol has been developed for fluorination of methylated uracils involving a stoichiometric amount of ionic liquid (IL) in alcohols. The fluorination of 6-methyluracil and 1,3,6-trimethyluracil has been carried out using the electrophilic fluorinating reagent Selectfluor™ (F-TEDA-BF4) in MeOH and EtOH solvents with the formation of 5-fluoro-6-methyluracil, 5-fluoro-1,3,6-trimethyluracil

  已经开发了一种新颖的有效方案，用于氟化甲基化尿嘧啶，涉及化学计量的醇中离子液体（IL）。6-甲基尿嘧啶和1,3,6-三甲基尿嘧啶的氟化已使用亲电氟化试剂Selectfluor™（F-TEDA-BF 4）在MeOH和EtOH溶剂中的形成，主要产物是5-氟-6-甲基尿嘧啶，5-氟-1,3,6-三甲基尿嘧啶以及二氟二氢尿嘧啶的α-氟甲氧基-和α-氟乙氧基醚。使用化学计量的离子液体作为添加剂可导致反应加速。已经发现的是，IL对反应速率的阴离子的效果更显着相比，阳离子的，阴离子以下列顺序降低的效果：[HSO 4 - ]> [光学传递函数- ] 〜[NTF 2 - ]> [BF 4 - ]> [PF 6 - ]。还评估了金属碳酸盐对氟尿嘧啶收率的影响。
• 一种2-氯-5-氟-6-甲基嘧啶的合成方法
  申请人：南京普锐达医药科技有限公司

  公开号：CN111484455A

  公开（公告）日：2020-08-04

  本发明涉及一种2‑氯‑5‑氟‑6‑甲基嘧啶的合成方法：将甲醇钠溶于甲醇中后，加入尿素搅拌，滴加2‑氟乙酰乙酸乙酯，回流反应2‑3小时得中间体A。中间体A，三氯氧磷和有机碱按重量比1:5‑10:0.3‑2混合反应，将混合物冷却后除去多余的三氯氧磷，加水淬灭萃取，干燥，浓缩后得到产物B。将产物B加入乙醇，锌粉，醋酸，加热回流反应10‑16小时，降温，过滤，蒸去乙醇，有机溶剂萃取，蒸干得粗品，减压精馏得纯品产物C，即为2‑氯‑5‑氟‑6‑甲基嘧啶。本方法具有提高了收率，缩短了时间，操作简单，简化了后处理工序的效果。
• Process for fluorinating uracil and derivatives thereof
  申请人：PCR, Inc.

  公开号：US03954758A1

  公开（公告）日：1976-05-04

  Direct fluorination of uracil and its derivatives, in the presence of an aqueous solvent, by fluorine gas to produce 5-fluorouracil and 5-fluorouracil derivatives is disclosed. Novel compounds produced by the reaction, such as 5,5-difluoro-6-hydroxy-5,6-dihydrouracil are also disclosed. The derivatives of 5-fluorouracil are useful as germicidal agents while 5-fluorouracil itself is a known cancer chemotherapy agent.

  本发明揭示了在水溶剂存在下，利用氟气对尿嘧啶及其衍生物进行直接氟化反应，以产生5-氟尿嘧啶和5-氟尿嘧啶衍生物。反应所产生的新化合物，例如5,5-二氟-6-羟基-5,6-二氢尿嘧啶也被揭示。5-氟尿嘧啶的衍生物可用作杀菌剂，而5-氟尿嘧啶本身是一种已知的癌症化疗药物。
• 5-Fluorouracil derivatives
  申请人：PCR, Inc.

  公开号：US04113949A1

  公开（公告）日：1978-09-12

  Direct fluorination of uracil and its derivatives, in the presence of an aqueous solvent, by fluorine gas to produce 5-fluorouracil and 5-fluorouracil derivatives is disclosed. Novel compounds produced by the reaction, such as 5,5-difluoro-6-hydroxy-5,6-dihydrouracil are also disclosed. The derivatives of 5-fluorouracil are useful as germicidal agents while 5-fluorouracil itself is a known cancer chemotherapy agent.

  本发明揭示了在水溶剂存在下，利用氟气对尿嘧啶及其衍生物进行直接氟化反应，以产生5-氟尿嘧啶和5-氟尿嘧啶衍生物。该反应产生的新化合物，如5,5-二氟-6-羟基-5,6-二氢尿嘧啶也被揭示。5-氟尿嘧啶的衍生物可用作杀菌剂，而5-氟尿嘧啶本身是已知的癌症化疗剂。
• Source regions and timescales for the delivery of water to the Earth
  作者：A. Morbidelli、J. Chambers、J. I. Lunine、J. M. Petit、F. Robert、G. B. Valsecchi、K. E. Cyr

  DOI：10.1111/j.1945-5100.2000.tb01518.x

  日期：2000.11

  Abstract—In the primordial solar system, the most plausible sources of the water accreted by the Earth were in the outer asteroid belt, in the giant planet regions, and in the Kuiper Belt. We investigate the implications on the origin of Earth's water of dynamical models of primordial evolution of solar system bodies and check them with respect to chemical constraints. We find that it is plausible that the Earth accreted water all along its formation, from the early phases when the solar nebula was still present to the late stages of gas‐free sweepup of scattered planetesimals. Asteroids and the comets from the Jupiter‐Saturn region were the first water deliverers, when the Earth was less than half its present mass. The bulk of the water presently on Earth was carried by a few planetary embryos, originally formed in the outer asteroid belt and accreted by the Earth at the final stage of its formation. Finally, a late veneer, accounting for at most 10% of the present water mass, occurred due to comets from the Uranus‐Neptune region and from the Kuiper Belt. The net result of accretion from these several reservoirs is that the water on Earth had essentially the D/H ratio typical of the water condensed in the outer asteroid belt. This is in agreement with the observation that the D/H ratio in the oceans is very close to the mean value of the D/H ratio of the water inclusions in carbonaceous chondrites.