3-butyl-2-thioxoimidazolidin-4-one | 162150-91-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-butyl-2-thioxoimidazolidin-4-one
• 英文别名: 3-butyl-2-thiohydantoin；N-butyl thiohydantoine；3-butyl-2-sulfanylideneimidazolidin-4-one
• CAS: 162150-91-6
• 化学式: C₇H₁₂N₂OS
• mdl: MFCD04967166
• 分子量: 172.251
• InChiKey: JIPAXYGBULGOLF-UHFFFAOYSA-N

物化性质

• 熔点：
  109.8-110.7 °C(Solv: hexane (110-54-3))
• 沸点：
  234.9±23.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.714
• 拓扑面积：
  64.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-butyl-2-thioxoimidazolidin-4-one 在 sodium tetrahydroborate 、 lithium chloride 、 过氧化苯甲酰 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 乙醇 为溶剂， 反应 6.5h， 生成 N-丁基咪唑
  参考文献：
  名称：

  氨基酸轻松转化为 1-烷基咪唑-2-硫酮，以及用过氧化苯甲酰将其氧化脱硫为咪唑

  摘要：

  甘氨酸用异硫氰酸酯酰化并缩合为 3-烷基 2-硫代乙内酰脲，再用硼氢化钠和氯化锂的混合物还原并脱水为 1-烷基咪唑-2-硫酮。用过氧化苯甲酰将它们氧化脱硫成咪唑。模型化合物不需要色谱。开发的方法用于将酪氨酸精制为 1,4-二（对甲氧基苄基）咪唑，这是从海绵 Leucetta 合成三种咪唑的常见中间体。

  DOI：

  10.1055/s-2007-983740
• 作为产物：
  描述：

  (3-Butyl-thioureido)-acetic acid ethyl ester 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 3-butyl-2-thioxoimidazolidin-4-one
  参考文献：
  名称：

  Substituted 2-Thioxoimidazolidin-4-ones and Imidazolidine-2,4-diones as Fatty Acid Amide Hydrolase Inhibitors Templates

  摘要：

  The demonstration of the essential role of fatty acid amide hydrolase (FAAH) in hydrolyzing endogenous bioactive fatty acid derivatives has launched the quest for the discovery of inhibitors for this enzyme. Along this line, a set of 58 imidazolidine-2,4-dione and 2-thioxoirnidazolidin-4-one derivatives was evaluated as FAAH inhibitors. Among these compounds, 3-substituted 5,5'-diplietiylimidazolidine-2,4-dione and 3-substituted 5,5'-diphenyl-2-thioxoimidazolidin-4-one derivatives were previously described as CB, cannabinoid receptor ligands. In the present study, we synthesized several derivatives exhibiting interesting FAAH inhibitory activity and devoid of affinity for the CB, and CB, cannabinoid receptors. For instance, 3-heptyl-5,5'-diphenylimidazolidine-2,4-dione (14) and 5.5'-diphenyl-3-tetradecyl-2-thioxo-imidazolidin-4-one (46) showed pI(50) values of 5.12 and 5.94, respectively. In conclusion, it appears that even though several 3-substituted 5,5'-diphenyl-2-thioxoimidazolidin-4-one and 3-substituted 5.5'-diphenylimidazolidine-2,4-dione derivatives have been previously shown to behave as CB, cannabinoid receptor ligands, appropriate substitutions of these templates can result in FAAH inhibitors devoid of affinity for the cannabinoid receptors.

  DOI：

  10.1021/jm050977k

文献信息

• A practical and eco-friendly synthesis of stereocontrolled alkylaminomethylidene derivatives of 2-thiohydantoins by dimethylamine substitution
  作者：Jean-René Chérouvrier、François Carreaux、Jean Pierre Bazureau

  DOI：10.1016/s0040-4039(02)02156-1

  日期：2002.11

  -4-ones 3(a–c) available in two steps from methyl glycinate hydrochloride, represent a useful synthetic tool for efficient and mild solventless preparations of new alkylaminomethylidene derivatives of 2-thiohydantoins 8(a–e), 10(a–c) and 12(a–d) by stereocontrolled transamination reactions under microwave irradiations. The 1H, 13C NMR spectrum and the (5Z)-conformation of some representatives products

  可从甘氨酸甲酯盐酸盐分两步获得的3-烷基-5-二甲基氨基亚甲基-2-硫代-咪唑啉丁-4-酮3（a – c）是有用的合成工具，可用于高效，温和的无溶剂制备2-的新烷基氨基亚甲基衍生物硫代乙内酰脲8（a - e），10（a - c）和12（a - d）在微波辐射下通过立体控制的氨基转移反应生成。的1个H，13 C NMR光谱和（5 ž）-一些代表性产品的构形也进行了讨论。
• Ryczek, J., Polish Journal of Chemistry, 1994, vol. 68, # 12, p. 2599 - 2604
  作者：Ryczek, J.

  DOI：——

  日期：——
• Synthesis of N,N′-bis(5-arylidene-4-oxo-3,5-dihydro-4H-imidazol-2-yl)diamines bearing various linkers and biological evaluation as potential inhibitors of kinases
  作者：Wacothon Karime Coulibaly、Ludovic Paquin、Anoubilé Bénie、Yves-Alain Bekro、Emilie Durieu、Laurent Meijer、Jean Pierre Bazureau

  DOI：10.1016/j.ejmech.2012.08.044

  日期：2012.12

  The synthesis in 4 steps of new N,N'-bis(5-arylidene-4-oxo-3,5-dihydro-4H-imidazol-2-yl)diamines issued from various symmetric primary diamines as linkers was reported. The key step of our strategy has been the sulphur/nitrogen displacement of (5Z)-5-arylidene-2-ethylsulfanyl-3,5-dihydro-4H-imidazol-4-ones 6 with respectively ethylenediamine 7a, piperazine 7b and N,N'-bis(3-aminopropyl)piperazine 7c using solvent-free reaction conditions under microwave irradiation with retention of configuration. These compounds were tested for their kinase inhibitory potencies toward four kinases (GSK-3 alpha/beta, DYRK1A, CLK1 and CLK3). Crown Copyright (C) 2012 Published by Elsevier Masson SAS. All rights reserved.
• Microwave-mediated solventless synthesis of new derivatives of marine alkaloid Leucettamine B
  作者：Jean-René Chérouvrier、François Carreaux、Jean Pierre Bazureau

  DOI：10.1016/s0040-4039(02)00575-0

  日期：2002.5

  New access to N-alkyl derivatives of the marine alkaloid Leucettamine B are described using two three-step convergent routes. For the formation of the 2-amino imidazolone ring, the key steps involve solvent-free condensations under microwaves and guanylation reactions with non-sterically hindered primary amines. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Microwave-assisted traceless synthesis of thiohydantoin
  作者：Mei-Jung Lin、Chung-Ming Sun

  DOI：10.1016/j.tetlet.2003.09.156

  日期：2003.11

  An efficient, microwave-assisted method for the liquid-phase combinatorial synthesis of 3,5-disubstituted-thiohydantoin has been developed. Fmoc-protected amino acids were coupled with HO-PEG-OH and after deprotection, reacted with various isothiocyanates in microwave cavity. The PEG bound thiourea compounds underwent base mediated cyclization/cleavage step by microwave flash heating. The desired products were then liberated from the soluble matrix in good yield and purity under microwave exposure. (C) 2003 Elsevier Ltd. All rights reserved.