3-phenyl-5-benzyl-hydantoin | 2221-08-1

• 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-phenyl-5-benzyl-hydantoin
• 英文别名: 3-phenyl-5-benzylhydantoin；5-benzyl-3-phenyl-imidazolidine-2,4-dione；5-Benzyl-3-phenyl-imidazolidin-2,4-dion；5-Benzyl-3-phenyl hydantoin；5-Benzyl-3-phenyl-hydantoin；5-Benzyl-3-phenylimidazolidine-2,4-dione
• CAS: 2221-08-1；138088-50-3
• 化学式: C₁₆H₁₄N₂O₂
• 分子量: 266.299
• InChiKey: MZPQMSNHXOWKHF-UHFFFAOYSA-N

物化性质

• 熔点：
  171 °C
• 密度：
  1.260±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  3-phenyl-5-benzyl-hydantoin 在 氢氧化钾 作用下， 生成 3-Phenyl-2-(3-phenylureido)-propionsaeure
  参考文献：
  名称：

  Lutsenko,V.V. et al., Journal of Organic Chemistry USSR (English Translation), 1971, vol. 7, # 6, p. 1186 - 1191

  摘要：

  DOI：
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 钯 作用下， 生成 3-phenyl-5-benzyl-hydantoin
  参考文献：
  名称：

  Bergmann; Delis, Justus Liebigs Annalen der Chemie, 1927, vol. 458, p. 83

  摘要：

  DOI：

文献信息

• Microwave-assisted solid-phase synthesis of hydantoin derivatives
  作者：Evelina Colacino、Frédéric Lamaty、Jean Martinez、Isabelle Parrot

  DOI：10.1016/j.tetlet.2007.05.084

  日期：2007.7

  5-substituted hydantoins starting from various resins for solid-phase combinatorial chemistry has been developed. The hydantoins were synthesized from pre-loaded resins with amino acids via treatment with isocyanate or phenylisocyanate and subsequent intramolecular cyclization. Both reactions were performed under microwave irradiation. We studied the cyclative cleavage leading to hydantoin compounds dependent

  已经开发了用于各种固相组合化学的微波辅助合成的各种树脂起始的3,5-和1,3,5-取代的乙内酰脲。乙内酰脲是通过用异氰酸酯或苯基异氰酸酯处理并随后进行分子内环化作用而由具有氨基酸的预载树脂合成的。两种反应均在微波辐射下进行。我们研究了导致乙内酰脲化合物的环化裂解，这取决于氨基酸的性质和树脂的核定性。
• Process for the preparation of hydantoin derivatives
  申请人：Teijin Ltd.

  公开号：US03946033A1

  公开（公告）日：1976-03-23

  Hydantoin derivatives are produced by reacting 1. a glycine derivative, 2. a primary amine, and 3. a diaryl carbonate Thus, various kinds of hydantoin derivatives can be obtained without using an isocyanate.

  Hydantoin衍生物是通过将1.甘氨酸衍生物，2.一种初级胺和3.二芳基碳酸酯反应而生产的。因此，可以获得各种种类的Hydantoin衍生物，而无需使用异氰酸酯。
• 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。
• Unprecedented One-Pot Chemocontrolled Entry to Thioxoimidazolidinones and Aminoimidazolones: Synthesis of Kinase Inhibitor Leucettamine B
  作者：Manikandan Selvaraju、Chung-Ming Sun

  DOI：10.1021/co500152s

  日期：2015.3.9

  A novel and highly chemoselective protocol for the construction of thioxoimidazolidinone and aminoimidazolone frameworks was explored, and the influence of the reaction conditions on product formation was studied to establish two distinct approaches for their selective formation. In this one-pot reaction, ambient temperature generally resulted in the formation of thioxoimidazolidinones, whereas microwave irradiation provided aminoimidazolones exclusively. An attempt to elucidate the observed chemoselectivity is described, and the products were confirmed by X-ray studies. One-pot synthesis toward Leucettamine B, a marine alkaloid, was achieved on the basis of this protocol.
• Johnson; Brautlecht, Journal of the American Chemical Society, 1911, vol. 33, p. 1537
  作者：Johnson、Brautlecht

  DOI：——

  日期：——