3-benzoyl-5-(2-bromovinyl)uracil | 185816-33-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-benzoyl-5-(2-bromovinyl)uracil
• 英文别名: 3-benzoyl-5-[(E)-2-bromoethenyl]-1H-pyrimidine-2,4-dione
• CAS: 185816-33-5
• 化学式: C₁₃H₉BrN₂O₃
• 分子量: 321.13
• InChiKey: YICWKGPYZJNWJP-VOTSOKGWSA-N

物化性质

• 密度：
  1.713±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 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：
  66.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-benzoyl-5-(2-bromovinyl)uracil 在 ammonium hydroxide 、 三氯化硼 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 5-((E)-2-Bromo-vinyl)-2-[(3S,4S,5R)-5-(tert-butyl-diphenyl-silanyloxymethyl)-4-hydroxy-tetrahydro-thiophen-3-yloxy]-3H-pyrimidin-4-one
  参考文献：
  名称：

  Synthesis of Novel Iso-4‘-thionucleosides Using the Mitsunobu Reaction

  摘要：

  A novel class of isomeric 4'-thionucleosides with the base moiety at the 2'-position was synthesized from D-glucose. The coupling of 1,4-anhydro-4-thioarabitol (13) with various nucleobases using the Mitsunobu reaction was investigated. With both purines and N-3-benzoyluracils, the reaction predominantly gave beta-isomers, suggesting that these were produced via an episulfonium intermediate. The beta-anomers produced by the reaction of N-3-benzoyluracils included both N- and O-alkylated derivatives. Interestingly, only the reaction of N-3-benzoyluracil gave a mixture of N-alkylated adduct (20d) and O-alkylated bipyrimidinyl adduct (22), the structure of which was unambiguously determined by NMR spectroscopic data including HMBC and NOE. Deprotection of the Mitsunobu reaction products gave the desired iso-4'-thionucleosides.

  DOI：

  10.1021/jo980667s
• 作为产物：
  描述：

  苯甲酰氯 、 (E)-5-(2-溴乙烯基)尿嘧啶 在 吡啶 作用下， 以 乙腈 为溶剂， 反应 60.0h， 以81%的产率得到3-benzoyl-5-(2-bromovinyl)uracil
  参考文献：
  名称：

  A Short, Convergent Synthesis of Two Chiral Antiviral Agents, (+) Carbocyclic 2′-Deoxy-5-[(E)-2-Bromovinyl] Uridine and (+) Carbocyclic 2′-DeoxyGuanosine

  摘要：

  DOI：

  10.1016/00404-0399(50)1372o-

文献信息

• New Convergent Synthesis of Carbocyclic Nucleoside Analogues
  作者：Chris Meier、Olaf R. Ludek

  DOI：10.1055/s-2003-41455

  日期：——

  Two convergent approaches towards the synthesis of carbocyclic nucleoside analogs will be described. Both approaches start from the stereochemically pure cyclopentenol 8 that has been prepared enantioselectively from an alkylated cyclopentadiene. Using these approaches, carbocyclic analogues of dT, FdU and BVdU have been prepared. Moreover, the conversion into the cycloSal-pronucleotide and the corresponding nucleotide will be presented for one example.

  将描述两种趋同的方法用于合成碳环核苷类似物。这两种方法均以从烷基化环戊二烯中选择性制备的立体化学纯环戊醇8为起点。通过这些方法，已合成出dT、FdU和BVdU的碳环类似物。此外，还将展示一种例子中转化为环Sal-前核苷酸及相应核苷酸的过程。
• Cyclopentane-Nucleobase Coupling in the Synthesis of Carbocyclic L-Nucleosides: is A S_<i>N</i>2-Reaction an Alternative to the Mitsunobu-Reaction?
  作者：S. Jessel、E. Hense、C. Meier

  DOI：10.1080/15257770701527745

  日期：2007.11.26

  Several carbocyclic L-nucleosides have been synthesized by coupling a cyclopentane-system with heterocycles according to a modified Mitsunobu-protocol. This reaction gave two regioisomers, the NI-alkylated product and an unwanted O-2-product. A simple, S(N)2-reaction has been investigated as an alternative for such couplings.
• Drake, Alex F.; Garofalo, Antonio; Hillman, Jennifer M. L., Journal of the Chemical Society. Perkin transactions I, 1996, # 22, p. 2739 - 2746
  作者：Drake, Alex F.、Garofalo, Antonio、Hillman, Jennifer M. L.、Merlo, Valeria、McCague, Ray、Roberts, Stanley M.

  DOI：——

  日期：——
• Synthesis of the phosphonate isostere of carbocyclic 5-bromovinyldeoxyuridine monophosphate
  作者：Diane M. Coe、Antonio Garofalo、Stanley M. Roberts、Richard Storer、Andrew J. Thorpe

  DOI：10.1039/p19940003061

  日期：——

  The nucleotide analogue 5 has been synthesized, via formation of the diet 11, and has been shown to be inactive against HSV in vitro. Resolution of the intermediate diol 11 was effected using a highly stereoselective enzyme-catalysed acetylation.
• Synthesis of Novel Iso-4‘-thionucleosides Using the Mitsunobu Reaction
  作者：Kohei Yamada、Shinji Sakata、Yuichi Yoshimura

  DOI：10.1021/jo980667s

  日期：1998.10.1

  A novel class of isomeric 4'-thionucleosides with the base moiety at the 2'-position was synthesized from D-glucose. The coupling of 1,4-anhydro-4-thioarabitol (13) with various nucleobases using the Mitsunobu reaction was investigated. With both purines and N-3-benzoyluracils, the reaction predominantly gave beta-isomers, suggesting that these were produced via an episulfonium intermediate. The beta-anomers produced by the reaction of N-3-benzoyluracils included both N- and O-alkylated derivatives. Interestingly, only the reaction of N-3-benzoyluracil gave a mixture of N-alkylated adduct (20d) and O-alkylated bipyrimidinyl adduct (22), the structure of which was unambiguously determined by NMR spectroscopic data including HMBC and NOE. Deprotection of the Mitsunobu reaction products gave the desired iso-4'-thionucleosides.