5-n-Amyl-5-methylhydantoin | 65826-54-2

• 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-n-Amyl-5-methylhydantoin
• 英文别名: 5-Methyl-5-n-pentylhydantoin；DL-5-Methyl-5-pentyl-hydantoin；5-methyl-5-n-amylhydantoin；5-methyl-5-pentyl-imidazolidine-2,4-dione；5-Methyl-5-pentyl-imidazolidin-2,4-dion；2,4-Imidazolidinedione, 5-methyl-5-pentyl-；5-methyl-5-pentylimidazolidine-2,4-dione
• CAS: 65826-54-2
• 化学式: C₉H₁₆N₂O₂
• 分子量: 184.238
• InChiKey: ZCZARJLJMRQNRB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 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-n-Amyl-5-methylhydantoin 在 barium dihydroxide 作用下， 生成 2-Amino-2-methyl-heptansaeure
  参考文献：
  名称：

  A New Series of Anticonvulsant Drugs: Branched-Chain α-Aminoacetamides

  摘要：

  DOI：

  10.1021/jo01358a022
• 作为产物：
  描述：

  2-庚酮 在 potassium cyanide 、 乙醇 、 碳酸氢铵 作用下， 生成 5-n-Amyl-5-methylhydantoin
  参考文献：
  名称：

  Identification of Carbonyl Compounds through Conversion into Hydantoins¹

  摘要：

  DOI：

  10.1021/ja01255a014

文献信息

• Facile one-pot synthesis of 5-substituted hydantoins
  作者：Ross G. Murray、David M. Whitehead、Franck Le Strat、Stuart J. Conway

  DOI：10.1039/b719675j

  日期：——

  5-Substituted and 5,5-disubstituted hydantoins are synthesised from the corresponding aldehydes or ketones, using a one-pot, gallium(III) triflate-catalysed procedure that is compatible with a range of substrates and solvents.

  5-取代和5,5-二取代海因是由相应的醛或酮通过一步法合成，采用与多种底物和溶剂兼容的镓(III)三氟甲磺酸盐催化过程。
• Rapid generation of molecular complexity using ‘sequenced’ multi-component reactions: one-pot synthesis of 5,5′-disubstituted hydantoins from methyleneaziridines
  作者：Cyril Montagne、Jason J. Shiers、Michael Shipman

  DOI：10.1016/j.tetlet.2006.10.135

  日期：2006.12

  2-Methyleneaziridines can be transformed into 5,5′-disubstituted hydantoins in moderate to good yield (48–75%) via a ‘one-pot’ process that brings together up to six components in an orchestrated way.

  可以通过“一锅法”将2-亚甲基氮丙啶以中等到良好的产率（48-75％）转化为5,5'-二取代的乙内酰脲，该过程以精心策划的方式将多达六个组分结合在一起。
• Modified Bucherer-Bergs Reaction for the One-Pot Synthesis of 5,5′-Disubstituted Hydantoins from Nitriles and Organometallic Reagents
  作者：Michael Shipman、Cyril Montagne

  DOI：10.1055/s-2006-949644

  日期：2006.9

  Diverse sets of 5,5'-disubstituted hydantoins can conveniently be made in moderate to good yields (40-92%) by a one-pot process involving treatment of aromatic, heteroaromatic or aliphatic nitriles with an organometallic reagent (RLi or RMgX) followed by KCN/(NH4)(2)CO3.

  通过一锅法，包括用有机金属试剂（RLi 或 RMgX）处理芳香族、杂芳香族或脂肪族腈，然后以中等至良好的产率 (40-92%) 方便地制备不同组的 5,5'-二取代乙内酰脲通过 KCN/(NH4)(2)CO3。
• Process for the preparation of dl-beta-aryl amino acids
  申请人：ALKALOIDA VEGYESZETI GYAR

  公开号：EP0156582A1

  公开（公告）日：1985-10-02

  The invention relates to a process for the preparation of DL-β-aryl-amino acids of the general Formula. wherein R,R, and R2 stand for hydrogen, halogen, C1-6 alkyl, C1-6 alkoxy, nitro or C1-4 dialkylamino. An aqueous solution of glycine and an excess of urea is heated and the reaction mixture is subjected to acidic cyclisation. The hydantoin thus obtained is reached with an aromatic aldehyde of the general Formula in aqueous solution in the presence of an excess of ethanolamine or morpholine. The 5-arylidene hydantoin derivative of the general Formula thus obtained is reduced quantitatively in a dilute alkaline medium with a Raney-nickel or a palladium-carbon catalyst to yield the corresponding 5-aryl-methyl-hydantoin derivative of the general Formula R which is subjected to alkaline hydrolysis. The corresponding DL-β-aryl amino acid of the general Formula V is obtained in high yield and may be isolated at the isoelectric point thereof

  本发明涉及一种通式为 DL-β-芳基氨基酸的制备工艺。 其中 R、R和R2代表氢、卤素、C1-6烷基、C1-6烷氧基、硝基或C1-4二烷基氨基。 加热甘氨酸和过量脲的水溶液，并对反应混合物进行酸性环化。将得到的海因与通式为 在过量乙醇胺或吗啉存在的水溶液中进行反应。通式中的 5-芳基海因衍生物 在稀碱性介质中用雷尼-镍或钯-碳催化剂进行定量还原，生成相应的通式 R 的 5-芳基-甲基海因衍生物。 进行碱性水解。相应的通式 V 的 DL-β-芳基氨基酸的产率很高，并可在其等电点处分离出来。
• US3966627A
  申请人：——

  公开号：US3966627A

  公开（公告）日：1976-06-29