丙氨酸-1-(苯基硫基)-2,4-咪唑烷二酮(1:1) | 7390-20-7

• 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: 丙氨酸-1-(苯基硫基)-2,4-咪唑烷二酮(1:1)
• 英文名称: (S)-5-methyl-3-phenyl-2-thioxoimidazolidin-4-one
• 英文别名: 5-methyl-3-phenyl-2-thioxo-imidazolidin-4-one；5-methyl-3-phenyl-2-thioxoimidazolidin-4-one；anilinothiazolinone-Ala；PTH-α-alanine；(5S)-5-methyl-3-phenyl-2-sulfanylideneimidazolidin-4-one
• CAS: 7390-20-7
• 化学式: C₁₀H₁₀N₂OS
• 分子量: 206.268
• InChiKey: XGPFPXALZVOKRI-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  丙氨酸-1-(苯基硫基)-2,4-咪唑烷二酮(1:1) 在 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 生成 (S)-N-propionyl-4-methyl-1-phenylimidazolidin-2-thione
  参考文献：
  名称：

  Investigation of the diastereoselective Mannich reaction using imidazolidin-2-thione as a chiral auxiliary

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2014.11.008
• 作为产物：
  描述：

  (2S)-N-[[4-[(3-methylimidazol-3-ium-1-yl)methyl]phenyl]methyl]-2-(phenylcarbamothioylamino)propanamide;tetrafluoroborate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 丙氨酸-1-(苯基硫基)-2,4-咪唑烷二酮(1:1)
  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

• Biodegradable Microspheres. 16. Synthesis of Primaquine–Peptide Spacers for Lysosomal Release from Starch Microparticles
  作者：Rossitsa Borissova、Bernard Lammek、Peter Stjärnkvist、Ingvar Sjöholm

  DOI：10.1002/jps.2600840226

  日期：1995.2

  tetrapeptide spacer arm for the rate of lysosomal enzymatic release of PQ can be possible. A third group, comprising epsilon-aminocaproic acid-PQ derivatives which lack a free alpha-amino group, was synthesized. This was done to study the importance of enzymes, other than aminopeptidases, during lysosomal degradation of these derivatives. To allow HPLC analysis of the pattern of degradation of tetrapeptide-PQ

  采用经典的肽合成方法合成了四组化合物，并为每组化合物开发了分析方法。其中两个是抗衰老药物伯氨喹（PQ）的四肽衍生物，其一般结构为NH2-X-Leu-Ala-Y-PQ。第一组，Y位置使用Leu，Tyr，Lys和Asp，而X为Ala；第二组，X位置使用Ala，Tyr，Lys和Asp在X位置，Y为Leu。这些衍生物旨在通过其游离的α-氨基与聚丙烯酸酯淀粉微粒（在我们实验室开发的溶同溶性药物载体）偶联。因此，对PQ的溶酶体酶促释放速率的四肽间隔臂的不同氨基酸组成的重要性的系统研究是可能的。第三组 合成了包含缺少游离α-氨基的ε-氨基己酸-PQ衍生物的化合物。这样做是为了研究在这些衍生物的溶酶体降解过程中除氨肽酶以外的酶的重要性。为了允许HPLC分析四肽-PQ衍生物的降解模式，还制备了一些较短的肽-PQ衍生物（第四组）。
• 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：——
• 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.
• CHEN, TENG-MAN;COUTANT, JOHN E., J. CHROMATOGR., 463,(1989) N, C. 95-106
  作者：CHEN, TENG-MAN、COUTANT, JOHN E.

  DOI：——

  日期：——
• BOUDAH, F.;GUERMOUCHE, M. H., ANALUSIS, 18,(1990) N, C. 483-486
  作者：BOUDAH, F.、GUERMOUCHE, M. H.

  DOI：——

  日期：——