1-benzoyl-5,5-dimethylhydantoin | 102617-87-8

• 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: 1-benzoyl-5,5-dimethylhydantoin
• 英文别名: Cambridge id 5766751；1-benzoyl-5,5-dimethylimidazolidine-2,4-dione
• CAS: 102617-87-8
• 化学式: C₁₂H₁₂N₂O₃
• 分子量: 232.239
• InChiKey: HKHHUXCFTMSKOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  1-benzoyl-5,5-dimethylhydantoin 在 三氯异氰尿酸 作用下， 以 乙腈 为溶剂， 以87%的产率得到1-benzoyl-3-chloro-5,5-dimethylhydantoin
  参考文献：
  名称：

  On the Chlorenium Source in the Asymmetric Chlorolactonization Reaction

  摘要：

  N-Acylated N-chlorohydantoins are shown to be competent chlorenium sources in the (DHQD)(2)PHAL-mediated asymmetric chlorolactonization. The derivatives demonstrate the exact role of the N1 and N3 chlorine atoms in the parent dichlorohydantoins with the N1 chlorine serving as an inductive activator and the N3 chlorine being delivered to the substrate. The putative associated catalyst/chlorine source complex was experimentally demonstrated through a series of matched/mismatched experiments employing chiral N-chlorinated hydantoins.

  DOI：

  10.1021/ol102850m
• 作为产物：
  描述：

  5,5-二甲基海因 以 吡啶 为溶剂， 反应 12.0h， 生成 1-benzoyl-5,5-dimethylhydantoin
  参考文献：
  名称：

  On the Chlorenium Source in the Asymmetric Chlorolactonization Reaction

  摘要：

  N-Acylated N-chlorohydantoins are shown to be competent chlorenium sources in the (DHQD)(2)PHAL-mediated asymmetric chlorolactonization. The derivatives demonstrate the exact role of the N1 and N3 chlorine atoms in the parent dichlorohydantoins with the N1 chlorine serving as an inductive activator and the N3 chlorine being delivered to the substrate. The putative associated catalyst/chlorine source complex was experimentally demonstrated through a series of matched/mismatched experiments employing chiral N-chlorinated hydantoins.

  DOI：

  10.1021/ol102850m

文献信息

• Substitution in the hydantoin ring. Part IX.<i>N</i>-cyanohydantoins
  作者：Juan Zinczuk、Orfeo O. Orazi、Renée A. Corral、Hugo Roncaglia

  DOI：10.1002/jhet.5570220419

  日期：1985.7

  The N1-and N3-cyanohydantoins, a new series of derivatives, were prepared by reaction of the parent hydantoin with a base and a cyanogen halide. Analysis of ir, pmr, and mass spectral data allowed the assignment of ring position-3 to the cyano group in derivatives IIa,b of 1,3-unsubstituted hydantoins. 3-Cyanohydantoins can transfer the cyano substituent to strong nucleophiles via an addition-elimination

  所述Ñ 1 -and Ñ 3个-cyanohydantoins，一系列新的衍生物的，通过用碱和卤化氰的父乙内酰脲反应而制备。通过对ir，pmr和质谱数据的分析，可以将环位置3分配给1,3-未取代的乙内酰脲衍生物IIa，b中的氰基。3-氰基乙内酰脲可以通过加成消除法将氰基取代基转移到强亲核体上。
• ZINCZUK, J.;ORAZI, O. O.;CORRAL, R. A.;RONCAGLIA, H., J. HETEROCYCL. CHEM., 1985, 22, N 4, 1025-1028
  作者：ZINCZUK, J.、ORAZI, O. O.、CORRAL, R. A.、RONCAGLIA, H.

  DOI：——

  日期：——
• US4013575A
  申请人：——

  公开号：US4013575A

  公开（公告）日：1977-03-22
• On the Chlorenium Source in the Asymmetric Chlorolactonization Reaction
  作者：Roozbeh Yousefi、Daniel C. Whitehead、Janet M. Mueller、Richard J. Staples、Babak Borhan

  DOI：10.1021/ol102850m

  日期：2011.2.18

  N-Acylated N-chlorohydantoins are shown to be competent chlorenium sources in the (DHQD)(2)PHAL-mediated asymmetric chlorolactonization. The derivatives demonstrate the exact role of the N1 and N3 chlorine atoms in the parent dichlorohydantoins with the N1 chlorine serving as an inductive activator and the N3 chlorine being delivered to the substrate. The putative associated catalyst/chlorine source complex was experimentally demonstrated through a series of matched/mismatched experiments employing chiral N-chlorinated hydantoins.