(S)-5-(1-甲基乙基)-3-苯基-2-硫代咪唑烷-4-酮 | 29635-81-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 中文名称: (S)-5-(1-甲基乙基)-3-苯基-2-硫代咪唑烷-4-酮
• 英文名称: (S)-5-isopropyl-3-phenyl-2-thioxoimidazolidin-4-one
• 英文别名: 5-isopropyl-3-phenyl-2-thioxoimidazolidin-4-one；(5S)-3-phenyl-5-propan-2-yl-2-sulfanylideneimidazolidin-4-one
• CAS: 29635-81-2
• 化学式: C₁₂H₁₄N₂OS
• 分子量: 234.322
• InChiKey: HEIKHJHSVLQGGN-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  64.4
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  (S)-5-(1-甲基乙基)-3-苯基-2-硫代咪唑烷-4-酮 在 lithium aluminium tetrahydride 、 四氯化钛 、 sodium hydride 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 15.67h， 生成 (2R,3R)-3-(4-bromophenyl)-3-hydroxy-1-[(S)-5-isopropyl-3-phenyl-2-thioxoimidazolidin-1-yl]-2-methylpropan-1-one
  参考文献：
  名称：

  （S）-4-异丙基-1-苯基咪唑烷基-2-硫酮在钛介导的羟醛反应中的不对称诱导及其在（R）-巴氯芬的对映选择性合成中的应用

  摘要：

  讨论了（S）-4-异丙基-1-苯基咪唑烷基-2-硫酮作为手性助剂在立体选择性丙酸酯和乙酸羟醛反应中的用途。此外，证明了使用手性助剂通过乙酸酯醛醇缩醛反应的（R）-baclofen的对映选择性合成。 钛-Aldol反应-不对称合成-手性助剂-立体选择性

  DOI：

  10.1055/s-0030-1260187
• 作为产物：
  描述：

  (2S)-3-methyl-N-[[4-[(3-methylimidazol-3-ium-1-yl)methyl]phenyl]methyl]-2-(phenylcarbamothioylamino)butanamide;tetrafluoroborate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以0.38 g的产率得到(S)-5-(1-甲基乙基)-3-苯基-2-硫代咪唑烷-4-酮
  参考文献：
  名称：

  Traceless Approach for the Synthesis of 3,5-Disubstituted Thiohydantoins on Functionalized Ionic-Liquid Support

  摘要：

  A traceless approach for the synthesis of 3,5-disubstituted thiohydantoins on a novel functionalized ionic-liquid support, 5, is described. Acylation of benzylamine functionalized ionic-liquid support with amino acids yielded ionic-liquid-supported amino acids, which reacted with isothiocyanates to afford ionic-liquid-supported thioureas. Following intramolecular cyclization cleavage from the ionic-liquid support by trifluoroacetic acid (TFA), the desired 3,5-disubstituted thiohydantoins were obtained in good yields and purities. The efficiency of this ionic-liquid-phase strategy facilitated isolation and analysis of intermediates and removal of excess reagents and by-products during the reaction process.

  DOI：

  10.1080/00397910903013697

文献信息

• Pavlik, Manfred; Kluh, Ivan; Pavlikova, Frantiska, Collection of Czechoslovak Chemical Communications, 1989, vol. 54, # 7, p. 1940 - 1954
  作者：Pavlik, Manfred、Kluh, Ivan、Pavlikova, Frantiska、Vasickova, Sona、Kostka, Vladimir

  DOI：——

  日期：——
• Investigation of the diastereoselective Mannich reaction using imidazolidin-2-thione as a chiral auxiliary
  作者：Liang Zhu、Cuifen Lu、Zuxing Chen、Guichun Yang、Yan Li、Junqi Nie

  DOI：10.1016/j.tetasy.2014.11.008

  日期：2015.1

  Titanium mediated asymmetric Mannich reactions using imidazolidin-2-thione as a chiral auxiliary proceeded in good yields and with high diastereoselectivity to afford the anti-products in the presence of PPh3 additive. A non-chelated transition state with the PPh3-bound titanium enolate was proposed to explain the stereochemistry of the product. Alcoholysis of the adducts with methanol cleaved the imidazolidin-2-thione auxiliary to give the methyl esters in good yields and with excellent ee values. (C) 2014 Elsevier Ltd. All rights reserved.
• Simple and Efficient Synthesis of 5-Substituted-3-phenyl-2-thioxoimidazolidin-4-one Derivatives from<i>S</i>-Amino Acids and Phenylisothiocyanate in Et₃N/DMF-H₂O
  作者：Asha D. Jangale、Yogesh B. Wagh、Yogesh A. Tayade、Dipak S. Dalal

  DOI：10.1080/00397911.2015.1052506

  日期：2015.8.18

  A concise approach for the transformation of various S-amino acids into the 5-alkyl-3-phenyl-2-thioxoimidazolidin-4-one heterocycles using phenylisothiocyanate is described. Phenylthiohydantoins of amino acid were synthesized at room temperature in Et3N/DMF-H2O with easy workup and excellent yields.
• 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.
• BOUDAH, F.;GUERMOUCHE, M. H., ANALUSIS, 18,(1990) N, C. 483-486
  作者：BOUDAH, F.、GUERMOUCHE, M. H.

  DOI：——

  日期：——