N(1),N(3)-二烯丙基尿嘧啶 | 6892-10-0

• 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: N(1),N(3)-二烯丙基尿嘧啶
• 英文名称: N-1,N-3-diallylated uracil
• 英文别名: N1,N3-diallyluracil；1,3-diallyluracil；1,3-diallyl-1H-pyrimidine-2,4-dione；1,3-Diallyl-pyrimidindion-2,4；N(1),N(3)-Diallyluracil；1,3-bis(prop-2-enyl)pyrimidine-2,4-dione
• CAS: 6892-10-0
• 化学式: C₁₀H₁₂N₂O₂
• 分子量: 192.217
• InChiKey: RDFAAIUDYVIXJT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 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：

  亚磷酸二甲酯 、 N(1),N(3)-二烯丙基尿嘧啶 在 二叔丁基过氧化物 作用下， 反应 6.0h， 以84.4%的产率得到1,3-二(3-二甲氧基磷酰丙基)嘧啶-2,4-二酮
  参考文献：
  名称：

  尿嘧啶和6-甲基尿嘧啶的1,3-二(3-二甲氧基磷酰基丙基)衍生物的合成及生物活性

  摘要：

  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]。

  DOI：

  10.1007/bf00765788
• 作为产物：
  描述：

  尿嘧啶 、 3-溴丙烯 生成 N(1),N(3)-二烯丙基尿嘧啶
  参考文献：
  名称：

  KOVALEV, G. V.;RAXIMOV, A. I.;OZEROV, A. A.;PETROV, V. I.;SPASOV, A. A.;V+, XIM.-FARMATS. ZH., 24,(1990) N, S. 25-27

  摘要：

  DOI：

文献信息

• Palladium(0)-catalysed allylation of uracils and thiouracils. Influence of the solvent on the regioselectivity of the allylation
  作者：Catherine Goux、Silvana Sigismondi、Denis Sinou、Montserrat Pérez、Marcial Moreno-Mañas、Roser Pleixats、Mercè Villarroya

  DOI：10.1016/0040-4020(96)00486-3

  日期：1996.7

  Uracil and 5-substituted uracils are monoallylated at N-1 in H2O-CH3CN with the catalytic (or tppts) although performing the reaction in H2O/THF with the system leads to diallylations at N-1 + N-3. 2-Thiouracil, 5-methyl-2-thiouracil (2-thiothymine) and 6-methyl-2-thiouracil are monoallylated at sulfur in with the catalytic system (or tppts). Performing the reactions in H2O/THF with the system leads

  尿嘧啶和5-取代的尿嘧啶在H 2 O-CH 3 CN中的N-1处被催化（或tppts）单芳基化，尽管在H 2 O / THF中与该体系进行反应会导致N-1 + N-处的二烯丙基化3。2-硫氧嘧啶，5-甲基-2-硫氧嘧啶（2-硫胸腺嘧啶）和6-甲基-2-硫氧嘧啶在硫磺中通过催化体系（或tppts）被单芳基化。在系统中于H 2 O / THF中进行反应会导致2-硫尿嘧啶和2-硫胸腺嘧啶在N-1 + N-3处进行烯丙基化，而6-甲基-2-硫尿嘧啶则在S + N-3处进行二烯丙基化。
• A new route to acyclic nucleosides via palladium-mediated allylic alkylation and cross-metathesis
  作者：Franck Amblard、Steven P. Nolan、Isabelle Gillaizeau、Luigi A. Agrofoglio

  DOI：10.1016/j.tetlet.2003.10.029

  日期：2003.12

  A method for the syntheses of E-unsaturated acyclic nucleosides via a combination of palladium-catalyzed allylic alkylation and ruthenium-based cross metathesis is described. This approach provides a concise, efficient and reliable route to new nucleoside analogues.

  描述了通过钯催化的烯丙基烷基化和基于钌的交叉复分解的组合来合成E-不饱和无环核苷的方法。这种方法为新的核苷类似物提供了简洁，有效和可靠的途径。
• Copper-Catalyzed Regioselective Direct C-H Thiolation and Thiocyanation of Uracils
  作者：Medena Noikham、Sirilata Yotphan

  DOI：10.1002/ejoc.201900343

  日期：2019.4.30

  The copper‐catalyzed direct C–H thiolation and thiocyanation of uracils using disulfides and thiocyanate salts respectively as coupling partners have been successfully developed. These protocols enable the C–H bond cleavage and C–S bond formation to proceed efficiently, providing useful methods to access of a diverse array of thio‐substituted at the 5 position of uracil derivatives in good to excellent

  已经成功开发了分别使用二硫化物和硫氰酸盐作为偶联伙伴的铜催化尿嘧啶的C–H直接硫醇化和硫氰化作用。这些规程使C–H键的裂解和C–S键的形成得以有效进行，从而提供了有用的方法，以优良的产率获得了尿嘧啶衍生物5位上的各种硫代取代基。
• 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。
• Efficient synthesis of various acycloalkenyl derivatives of pyrimidine using cross-metathesis and Pd(0) methodologies
  作者：Franck Amblard、Steven P. Nolan、Raymond F. Schinazi、Luigi A. Agrofoglio

  DOI：10.1016/j.tet.2004.11.019

  日期：2005.1

  Novel acyclonucleosides (9a-d, 10a-d, 18a,b and 19a,b) have been prepared using Pd(0) and cross-metathesis methodologies. The allylic N-alkylation under Tsuji-Trost conditions was used to introduce the nucleobase, while the Suzuki-Miyaura reaction afforded C-5 substituted uracil analogues. The cross-metathesis performed with a ruthenium catalyst was used to provide new acycloalkenyl nucleosides. The antiviral activities of all final compounds have been evaluated. (C) 2004 Elsevier Ltd. All rights reserved.