5-(benzylidene)-1-methylhydantoin | 31113-70-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 5-(benzylidene)-1-methylhydantoin
• 英文别名: 5-benzylidene-1-methyl-imidazolidine-2,4-dione；5-Benzyliden-1-methyl-imidazolidin-2,4-dion；3-Methyl-2.5-dioxo-4-benzyliden-imidazolidin；5-Benzylidene-1-methylimidazolidine-2,4-dione；5-benzylidene-1-methylimidazolidine-2,4-dione
• CAS: 31113-70-9
• 化学式: C₁₁H₁₀N₂O₂
• 分子量: 202.213
• InChiKey: KTEHTGGNHJQFHF-UHFFFAOYSA-N

物化性质

• 熔点：
  193-194 °C
• 密度：
  1.291±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(benzylidene)-1-methylhydantoin 在 氯磺酸 作用下， 以 甲醇 为溶剂， 反应 17.0h， 生成
  参考文献：
  名称：

  Cremlyn, Richard; Jethwa, Sanjay; Joiner, Graham, Phosphorus and Sulfur and the Related Elements, 1988, vol. 36, p. 99 - 110

  摘要：

  DOI：
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 barium dihydroxide 作用下， 生成 5-(benzylidene)-1-methylhydantoin
  参考文献：
  名称：

  Nicolet; Campbell, Journal of the American Chemical Society, 1928, vol. 50, p. 1158

  摘要：

  DOI：

文献信息

• Reasons Why Aldehydes Do Not Generally Participate in Cucurbit[<i>n</i>]uril Forming Reactions
  作者：Da Ma、Zuzana Gargulakova、Peter Y. Zavalij、Vladimir Sindelar、Lyle Isaacs

  DOI：10.1021/jo100186q

  日期：2010.5.7

  stable than the C-shaped diastereomers which we attribute to the conformational preferences of the newly formed benzo bicyclo[3.3.2]decane ring system. The preferential formation of S-shaped subunits is one reason why o-phthalaldehyde and possibly other aldehydes do not usually participate in CB[n] forming reactions. We also present evidence that points toward an equilibrium between glycoluril monomer

  取代的甘脲或甘脲二聚体与二醛（邻苯二甲醛）的反应选择性地产生S形二聚体和S形四聚体。X射线晶体学，PM3计算和产物再提交实验相结合，发现S形异构体在热力学上比C形非对映异构体稳定，这归因于新形成的苯并双环的构象偏爱[3.3.2]癸烷环系统。S形亚基的优先形成是邻苯二甲醛和其他可能的醛通常不参与CB的原因之一[ n形成反应。我们还提供了证据表明，甘脲单体+苯甲醛与S形二聚体+水之间存在平衡，该平衡对1-50 mM范围内的浓度有响应。该结果表明第二个原因，即反应性不足（例如，低的平衡常数），为什么邻苯二甲醛和可能的其他醛不参与CB [ n ]的形成反应。描述一些醛在这些反应中失败的原因是设计克服这些限制的方法的第一步。
• Diethyl 2,4-dioxoimidazolidine-5-phosphonates: Horner-Wadsworth-Emmons reagents for the mild and efficient preparation of C-5 unsaturated hydantoin derivatives
  作者：Nicholas A. Meanwell、Herbert R. Roth、Edward C. R. Smith、Donald L. Wedding、J. J. Kim Wright

  DOI：10.1021/jo00024a036

  日期：1991.11

  The phosphonates 19 and 20 were prepared from hydantoin and 1-methylhydantoin, respectively, by way of bromination at C-5 and a subsequent Michaelis-Arbuzov reaction with triethyl phosphite. The Horner-Wadsworth-Emmons-type reagents 19 and 20 were found to react readily with aromatic and aliphatic aldehydes, in the presence of a base, to produce C-5 unsaturated hydantoin derivatives 22 and 26, generally in high yield. The products 22 and 26 were frequently isolated as mixtures of E and Z isomers depending upon the identity of the aldehyde and phosphonate. The isomeric configuration of the products was determined from an analysis of NMR spectral data. Long-range C-13-H-1 coupling constants between the C-4 carbonyl of the hydantoin ring and the olefinic proton were found to be diagnostic of isomer geometry. Conditions were also developed that allowed coupling of 19 and 20 with cyclic and acyclic ketones and alpha-dicarbonyl compounds to afford the corresponding olefinic products. C-5 unsaturated hydantoin derivatives are of synthetic utility as precursors to alpha-amino acid derivatives, pyruvates, and the imidazo[4,5-b]quinolin-2-one heterocyclic ring system, a class of potent inhibitors of low Km cAMP phosphodiesterase and the chromophore present in the siderophore azotobactin.
• Fukuyama, Journal of Biochemistry, 1941, vol. 33, p. 73,74
  作者：Fukuyama

  DOI：——

  日期：——