3,5-dibenzyltetrahydro-1H-imidazole-2,4-dione | 2221-11-6

• 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: 3,5-dibenzyltetrahydro-1H-imidazole-2,4-dione
• 英文别名: 3,5-dibenzylimidazolidine-2,4-dione；3,5-dibenzyl-hydantoin；3,5-dibenzyl-imidazolidine-2,4-dione；3,5-dibenzylhydantoin；3.5-Dibenzyl-hydantoin；2,4-Imidazolidinedione, 3,5-bis(phenylmethyl)-
• CAS: 2221-11-6
• 化学式: C₁₇H₁₆N₂O₂
• 分子量: 280.326
• InChiKey: DGDSEHIUUMNLCW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.176
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  methyl (2S)-2-{[(benzylamino)carbonyl]amino}-3-phenylpropanoate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以34%的产率得到3,5-dibenzyltetrahydro-1H-imidazole-2,4-dione
  参考文献：
  名称：

  利用氢化铝锂合成一系列 3,5-二取代四氢-1H-咪唑-2,4-二酮

  摘要：

  摘要 利用氢化铝锂作为环化剂，从相应的尿素甲酯前体合成了一系列 3,5-二取代四氢-1H-咪唑-2,4-二酮。

  DOI：

  10.1081/scc-120003149

文献信息

• Facile One-Pot Synthesis of Substituted Hydantoins from Carbamates
  作者：Manjinder Gill、Dinesh Tanwar、Anjali Ratan

  DOI：10.1055/s-0036-1588468

  日期：2017.10

  A novel and simple approach for the preparation of 3-substituted, 5-substituted, or 3,5-disubstituted hydantoins is reported. It involves the reaction of α-amino methyl ester hydrochlorides with carbamates to yield the corresponding ureido derivatives, which subsequently cyclize under basic conditions to produce substituted ­hydantoins in good yields. By applying this method, the bioactive anticonvulsant

  报道了一种制备 3-取代、5-取代或 3,5-二取代乙内酰脲的新颖且简单的方法。它涉及 α-氨基甲酯盐酸盐与氨基甲酸酯反应生成相应的脲基衍生物，随后在碱性条件下环化以高产率生成取代的乙内酰脲。应用该方法合成了生物活性抗惊厥药物乙妥英，收率良好。该过程避免了传统的多步骤方案，并且不使用通常用于合成这些重要化合物的危险、刺激性、有毒或对水分敏感的试剂，如异氰酸酯或氯甲酸酯。
• Hydantoin compounds, their preparation and pharmaceutical formulations containing them
  申请人：Lilly Industries Limited

  公开号：EP0005647A1

  公开（公告）日：1979-11-28

  Hydantoin compounds are described, having the following formula wherein Ar is phenyl optionally substituted by up to three radicals selected from the group comprising C1-6 alkoxy, halogen, 1,3-dioxol-2-yl, hydroxy C1-4 alkoxy C1-4 alkyl, phenyl, hydroxyl, nitrile, C1-4 haloalkyl, C1-4 alkyl, C2-4 alkenyloxy, C1-4 alkoxycarbonyl or phenoxy optionally substituted by C1-4 haloalkyl, C1-4 alkoxy or halogen; or is thiophene optionally substituted by phenyl or by one or two C1-4 alkyl groups; R' and R2 are independently hydrogen or taken together represent a chemical bond; R3 is hydrogen, C1-6 alkyl or C2-4 alkenyl; and R4 is C1-6 alkyl, C2-4 alkenyl, phenyl or benzyl; provided that R3 cannot be hydrogen when Ar is unsubstituted phenyl and R4 is n-butyl. The compounds are useful in the prophylactic treatment of asthma in mammals.

  所述的海因化合物具有下式 其中 Ar 是苯基，可任选被最多三个基团取代，这三个基团选自 C1-6 烷氧基、卤素、1,3-二氧戊环-2-基、羟基 C1-4 烷氧基、C1-4 烷基、苯基、羟基、腈基、C1-4 卤代烷基、C1-4 烷基、C2-4 烯氧基、C1-4 烷氧羰基或任选被 C1-4 卤代烷基、C1-4 烷氧基或卤素取代的苯氧基； 或任选被苯基或一个或两个 C1-4 烷基取代的噻吩； R' 和 R2 独立为氢或共同代表一个化学键； R3 是氢、C1-6 烷基或 C2-4 烯基；以及 R4 是 C1-6 烷基、C2-4 烯基、苯基或苄基； 但当 Ar 为未取代苯基且 R4 为正丁基时，R3 不能为氢。 这些化合物可用于哺乳动物哮喘的预防性治疗。
• NMR spectroscopic and theoretical structural analysis of 5-benzyl substituted hydantoins in solution
  作者：R. Benassi、A. Bregulla、D. Henning、M. Heydenreich、G. Kempter、E. Kleinpeter、F. Taddei

  DOI：10.1016/s0022-2860(98)00506-7

  日期：1999.2

  The vicinal H,H and H,C coupling constants along the Ph-CH2AB-CRHM-C-X(=O)R' spin system of 5-benzyl substituted hydantoins together with the results of accompanying force field (TRIPOS) and quantum chemical ab initio calculations (GAUSSIAN-94 with atomic basis set of 3-21G type) were employed to report on the rotamer population about the hydantoin C(5)-benzyl substituent bond. The conformation having the phenyl ring folded over the hydantoin ring system proved to be preferred. (C) 1999 Elsevier Science B.V. All rights reserved.
• Preparation of Hydantoins by Catalytic Oxidative Carbonylation of α-Amino Amides
  作者：Seth M. Dumbris、Delmy J. Díaz、Lisa McElwee-White

  DOI：10.1021/jo9016138

  日期：2009.11.20

  Hydantoins can be synthesized from the corresponding amino amides employing oxidative catalytic carbonylation using W(CO)(6) as the catalyst, I-2 as the oxidant, CO as the carbonyl source, and DBU as base. Secondary amides afford the hydantoins in good to excellent yields, which decrease as the steric bulk of the N-alkyl substituent increases.
• US4241073A
  申请人：——

  公开号：US4241073A

  公开（公告）日：1980-12-23