5-(phenylselanyl)pyrimidine-2,4(1H,3H)-dione | 70291-89-3

• 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: 5-(phenylselanyl)pyrimidine-2,4(1H,3H)-dione
• 英文别名: 5-Phenyl selenylu-racil；5-phenylselanyl-1H-pyrimidine-2,4-dione
• CAS: 70291-89-3
• 化学式: C₁₀H₈N₂O₂Se
• 分子量: 267.146
• InChiKey: ZEGGHGSNGZPEHQ-UHFFFAOYSA-N

物化性质

• 熔点：
  250-252 °C (decomp)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.28
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(phenylselanyl)pyrimidine-2,4(1H,3H)-dione 、 间氯过氧苯甲酸 以66%的产率得到
  参考文献：
  名称：

  ANZAI K., J. HETEROCYCL. CHEM., 1979, 16, HO 3, 567-569

  摘要：

  DOI：
• 作为产物：
  描述：

  5-(phenylselenenyl)-2,4-bis(benzyloxy)pyrimidine 在 碘代三甲硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以78%的产率得到5-(phenylselanyl)pyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Phenylselenenyl- and phenylthio-substituted pyrimidines as inhibitors of dihydrouracil dehydrogenase and uridine phosphorylase

  摘要：

  Lithiation of 5-bromo-2,4-bis (benzyloxy) pyrimidine (3) with n-BuLi at -80 degrees C followed by the addition of diphenyl diselenide or diphenyl disulfide as an electrophile furnished the corresponding 5-(phenylhetera)-2,4-bis(benzyloxy) pyrimidine, which on exposure to trimethylsilyl iodide in CH2-Cl-2 at room temperature yielded the 5-(phenylhetera)uracils in 70-75% yield. Similarly, the 6-(phenylhetera) uracils were prepared from 6-bromo-2,4-bis (benzyloxy) pyrimidine (10). 1-[(2-Hydroxyethoxy)methyl] -5-(phenylselenenyl)uracil (PSAU, 18) and 1-(ethoxymethyl)-5- (phenylselenenyl)uracil (17) were synthesized by the electrophilic addition of benzeneselenenyl chloride to the acyclic uracils under basic conditions. These compounds were evaluated for their ability to inhibit dihydrouracil dehydrogenase (DHUDase, E.C. 1.3.1.2), orotate phosphoribosyltransferase (OPRTase, E.C. 2.4.2.10), uridine phosphorylase (UrdPase, E.C. 2.4.2.3), and thymidine phosphorylase (dThdPase, E.C. 2.4.2.4). 5-(Phenylselenenyl)uracil (PSU, 6) and 5-(phenylthio)uracil (PTU, 7) inhibited DHUDase with apparent K-i values of 4.8 and 5.4 mu M, respectively. The corresponding 6-analogues, compounds 13 and 14, demonstrated inhibitory activity against OPRTase. PTU as well as PSU and its riboside, 2'-deoxyriboside, and acyclonucleosides were inhibitors of UrdPase, with PSAU (18) being the most potent with an apparent K-i value of 3.8 mu M. None of the compounds evaluated had any effect on dThdPase. Interestingly, most of the compounds showed modest selective anti-human-immunodeficiency-virus activity in acutely infected primary human lymphocytes.

  DOI：

  10.1021/jm00078a015

文献信息

• Synthesis of substituted uracils by the reactions of halouracils with selenium, sulfur, oxygen and nitrogen nucleophiles under focused microwave irradiation
  作者：Woei-Ping Fang、Yuh-Tsyr Cheng、Yann-Ru Cheng、Yie-Jia Cherng

  DOI：10.1016/j.tet.2005.01.085

  日期：2005.3

  Under microwave irradiation, the nucleophilic substitution reactions of halouracils with selenium, sulfur, oxygen and nitrogen nucleophiles was complete within several minutes with yields up to 99%. The method using microwave irradiation is superior to those conducted under conventional heating processes.

  在微波辐射下，氟脲与硒，硫，氧和氮亲核试剂的亲核取代反应在几分钟内完成，收率高达99％。使用微波辐射的方法优于在常规加热过程下进行的方法。
• 制备5-硫/硒修饰尿嘧啶衍生物的方法
  申请人：中国科学院化学研究所

  公开号：CN109651267B

  公开（公告）日：2020-05-19

  本发明属于有机化学领域，具体涉及一种高效制备5‑硫/硒修饰尿嘧啶衍生物的方法。所述方法为：在碘源、氧化剂存在下，在溶剂中，使得式I所示硫酚类化合物或式II所示二硒醚类化合物与式III所示尿嘧啶反应，得到式IV所示5‑硫修饰尿嘧啶衍生物或式V所示5‑硒修饰尿嘧啶衍生物。本发明提供了一种无金属催化，无预先官能化的一步法制备硫/硒修饰尿嘧啶类化合物的通用方法，该方法绿色简洁可行，原料简单易得，底物范围广，应用前景广泛。
• A NaI/H₂O₂-Mediated Sulfenylation and Selenylation of Unprotected Uracil and Its Derivatives
  作者：Xue-Dong Li、Yu-Ting Gao、Ying-Jie Sun、Xiao-Yang Jin、Dong Wang、Li Liu、Liang Cheng

  DOI：10.1021/acs.orglett.9b02183

  日期：2019.9.6

  efficient iodide-catalyzed/hydrogen peroxide mediated sulfenylation and selenylation of unprotected uracil and its derivatives with simple thiols and diselenides was established. This coupling tolerates a broad variety of functional groups to provide diverse 5-sulfur/selenium-substituted uracil derivatives in good to excellent yields (up to 93%).

  建立了有效的碘化物催化/过氧化氢介导的未保护的尿嘧啶及其衍生物与简单硫醇和二硒化物的亚磺酰化和硒基化反应。这种偶联耐受多种官能团，以良好至极佳的收率（高达93％）提供各种5-硫/硒取代的尿嘧啶衍生物。
• Practical and sustainable approach for clean preparation of 5-organylselanyl uracils
  作者：Jin-Yang Chen、Chun-Tao Zhong、Qing-Wen Gui、Yuan-Ming Zhou、Yang-Yang Fang、Kai-Jian Liu、Ying-Wu Lin、Zhong Cao、Wei-Min He

  DOI：10.1016/j.cclet.2020.09.034

  日期：2021.1

  Abstract An eco-friendly, sustainable and practical method for the efficient preparation of 5-organylselanyl uracils through the electrochemical selenylation of uracils and diorganyl diselenides at room temperature under oxidant- and external electrolyte-free conditions was developed.

  摘要开发了一种环保，可持续，实用的方法，该方法可在室温下在无氧化剂和无外部电解质的条件下，通过尿嘧啶和二有机基二硒化物的电化学硒化作用来高效制备5-有机基硒基尿嘧啶。
• Electrochemical Synthesis of 5-Selenouracil Derivatives by Selenylation of Uracils
  作者：Qian Wang、Xian-Li Ma、Yan-Yan Chen、Cai-Na Jiang、Yan-Li Xu

  DOI：10.1002/ejoc.202000637

  日期：2020.8.2

  simple and efficient electrochemical selenylation of uracils in the presence of NH4I for the synthesis of 5‐selenouracils has been developed. This transformation was performed in the transition metal‐free, oxidant‐free, and air conditions, providing a rapid and practical protocol to 5‐selenouracil derivatives.

  已经开发了一种在NH 4 I存在下用于合成5-硒尿嘧啶的简单而有效的尿嘧啶电化学硒化反应。该转化是在无过渡金属，无氧化剂和空气条件下进行的，为5-硒代尿嘧啶衍生物提供了快速而实用的方案。