1,3-dimethyl-5-(phenylselanyl)pyrimidine-2,4(1H,3H)-dione | 135067-69-5

• 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: 1,3-dimethyl-5-(phenylselanyl)pyrimidine-2,4(1H,3H)-dione
• 英文别名: 1,3-Dimethyl-5-phenylselanylpyrimidine-2,4-dione
• CAS: 135067-69-5
• 化学式: C₁₂H₁₂N₂O₂Se
• 分子量: 295.199
• InChiKey: TYQOGULNUJKEAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.26
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,3-dimethyl-5-(phenylselanyl)pyrimidine-2,4(1H,3H)-dione 在 sodium hydride 、 magnesium monoperoxyphthalate hexahydrate 作用下， 以 四氢呋喃 、 乙醇 、 水 、 乙腈 为溶剂， 反应 17.0h， 生成 6-chloromethyl-1,3-dimethyluracil
  参考文献：
  名称：

  Development of Reactions of 6- and 5-Substituted 1,3-Dimethyluracils with Dimethylsulfoxonium Methylide

  摘要：

  6-Chloro-1,3-dimethyluracil (1) reacts with dimethylsulfoxonium methylide (3, 2 equiv) to give sulfoxonium ylide 8 (51%). The structure of 8 is established spectroscopically and by its reactions with various electrophiles and electron-deficient olefins. Thus, 8 is converted by HCl to sulfoxonium chloride ?, which then yields the 6-(chloromethyl)uracil 17 by heating in acetonitrile. Ylide 8 undergoes deuterium exchange at the Ei-position, at its methine carbon, and into its methyl groups attached to sulfur. Reaction of 8 with benzoyl chloride gives the highly substituted ylide 19 or the nucleophilic substitution products 17 and 18 depending on reaction conditions. Treatment of 8 with electron-deficient olefins yields 6-cyclopropyluracils 20-31. Many of the cyclopropyluracils have been converted to trans-1-(1,3-dimethyluracilyl)-2-vinylcylopropanes and cycloheptenyluracils. Reactions of 5-substituted uracils 2 (Z = SOPh and SeOPh) with ylide 3 have been developed. 5-(Phenylsulfinyl)uracil 48 yields cyclothymine derivative 49; 5-phenylseleninyluracil 52 gives methylide 8 as the major product.

  DOI：

  10.1021/jo981906e
• 作为产物：
  描述：

  1,3-二甲基脲嘧啶 、 二苯基二硒醚 在 potassium iodide 作用下， 以 二甲基亚砜 为溶剂， 反应 14.0h， 以90%的产率得到1,3-dimethyl-5-(phenylselanyl)pyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  实用且可持续的清洁制备5-organylselanyl尿嘧啶的方法

  摘要：

  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。

  DOI：

  10.1016/j.cclet.2020.09.034

文献信息

• 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。
• 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。
• Silver-catalyzed three-component reaction of uracils, arylboronic acids, and selenium: synthesis of 5-arylselanyluracils
  作者：Yuki Murata、Saori Tsuchida、Rena Nezaki、Yuki Kitamura、Mio Matsumura、Shuji Yasuike

  DOI：10.1039/d2ra01685k

  日期：——

  Herein, we describe a simple and general multi-component synthesis of 5-arylselanyluracils by the regioselective C–H selenation of uracils. Reactions of uracils with arylboronic acid and Se powder in the presence of AgNO3 (10 mol%) at 120 °C under aerobic conditions afforded various 5-arylselanyluracils. The source of the introduced selanyl group was prepared from a commercially available arylboronic

  在此，我们描述了通过尿嘧啶的区域选择性 C-H 硒化合成 5-芳基硒基尿嘧啶的简单而通用的多组分合成方法。在有氧条件下，在 120 °C和 AgNO 3 (10 mol%)存在下，尿嘧啶与芳基硼酸和硒粉的反应得到各种 5-芳基硒基尿嘧啶。引入的二硒基团的来源是由反应体系中的市售芳基硼酸和硒粉制备的，从而确保了简单有效的方案。该反应代表了在多组分系统中合成 5-芳基硒尿嘧啶的第一个例子。
• Iodine/persulfate-promoted site-selective direct thiolation of quinolones and uracils
  作者：Danupat Beukeaw、Medena Noikham、Sirilata Yotphan

  DOI：10.1016/j.tet.2019.130537

  日期：2019.9

  A simple and general method for direct thiolation of 4-quinolones with disulfides or thiols under I-2/K2S2O8 system has been developed. Under the optimal conditions, the C-S bond coupling can take place effectively with good to decent yields and excellent regioselectivity of the S-linked products. The established metal-free site-selective approach was also applicable to transform a range of uracil substrates to the thio-substituted products under mild conditions. Further transformation to the sulfone derivatives can be conveniently performed in one-pot. These easy-to-handle protocols represent a useful and interesting synthetic alternative with good substrate scope and functional group compatibility. (C) 2019 Elsevier Ltd. All rights reserved.