5-{[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]-methyl}-2-thioxo-4-thiazolidinone | 107902-68-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-{[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]-methyl}-2-thioxo-4-thiazolidinone
• 英文别名: 5-(3,5-di-tert-butyl-4-hydroxyphenylmethyl)-4-oxo-2-thiazolidinethione；5-{[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]}-methyl-2-thioxo-4-thiazolidinone；5-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methyl]-2-thioxo-4-thiazolidinone；5-{[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methyl}-2-thioxo-4-thiazolidinone；5-[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-2-sulfanylidene-1,3-thiazolidin-4-one
• CAS: 107902-68-1
• 化学式: C₁₈H₂₅NO₂S₂
• 分子量: 351.534
• InChiKey: PWRGVTODAPJEIP-UHFFFAOYSA-N

物化性质

• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-{[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]-methyl}-2-thioxo-4-thiazolidinone 在 盐酸 、 ammonium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 生成 3-(3,5-Ditert-butyl-4-hydroxyphenyl)-2-(hydroxymethylsulfanyl)propanamide
  参考文献：
  名称：

  Product Structure as a Function of Reaction Conditions in the Reaction of Formaldehyde with an Alpha-Mercapto Amide

  摘要：

  DOI：

  10.3987/com-98-8138
• 作为产物：
  描述：

  3,5-二叔丁基-4-羟基苯甲醛 在 二氢吡啶 、 sodium acetate 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 29.5h， 生成 5-{[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]-methyl}-2-thioxo-4-thiazolidinone
  参考文献：
  名称：

  Synthesis of enantioenriched 4-thiazolidinone (−)-LY213829 by chemoselective benzylamide cleavage in the presence of a C-S bond

  摘要：

  (R)-2-Methylbenzylamine has been used to covalently ''resolve'' thiol acid 7 and assemble 4-thiazolidinone 8a in one step. Selective deprotection of the 2-methylbenzylamide using lithium in ammonia/THF has been achieved in the presence of a readily hydrogenolyzed C-S bond. Enantioenriched (-)-LY213829 (1) of 98% ee has been prepared by this five step route in 25% yield from aldehyde 2. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00321-7

文献信息

• Synthesis of 4-thiazolidinones from rhodanines by thiocarbonyl removal
  作者：Marvin M. Hansen、Allen R. Harkness

  DOI：10.1016/0040-4039(94)88201-0

  日期：1994.9

  A new procedure for synthesis of 4-thiazolidinones from readily available rhodanines is reported. Slow addition of the substrate to excess zinc dust in acetic acid at reflux affords the best yields. Identification of dimeric byproducts led to development of a procedure to suppress their formation.

  报道了一种从容易获得的罗丹酮合成4-噻唑烷酮的新方法。将底物缓慢添加到过量的醋酸乙酸锌粉中，回流可获得最佳收率。二聚体副产物的鉴定导致抑制其形成的方法的发展。
• Aryl-substituted rhodanine derivatives
  申请人：Eli Lilly and Company

  公开号：US05356917A1

  公开（公告）日：1994-10-18

  Provided are certain aryl-substituted rhodanine derivatives, treatment methods and pharmaceutical formulations thereof.

  提供了某些含芳基取代的罗丹宁衍生物，以及其治疗方法和制药配方。
• Method for treating multiple sclerosis
  申请人：Eli Lilly and Company

  公开号：US05731336A1

  公开（公告）日：1998-03-24

  Provided is a method of treating multiple sclerosis employing certain aryl-substituted rhodanines.

  提供了一种利用特定芳基取代的硫氰酸酯治疗多发性硬化症的方法。
• Method of treating type I diabetes
  申请人：The University of Colorado Foundation, Inc.

  公开号：US05158966A1

  公开（公告）日：1992-10-27

  Provided is a method for treating Type I diabetes in mammals utilizing certain aryl-substituted rhodanine derivatives.

  提供了一种利用特定芳基取代的罗丹宁衍生物治疗哺乳动物I型糖尿病的方法。
• Process for preparing benzyl-substituted rhodanine derivatives
  申请人：Eli Lilly and Company

  公开号：US05563277A1

  公开（公告）日：1996-10-08

  The instant invention provides a novel process for preparing benzyl-substituted rhodanine derivatives. The process is particularly useful for synthesizing the enantiomers of such derivatives. Also provided are novel benzyl-substituted mercaptopropanoic acids and benzyl-substituted thiazolidinones. Such compounds are useful for treating inflammatory bowel disease and, accordingly, the present invention provides a method of treating inflammatory bowel disease in mammals utilizing such novel compounds as well as pharmaceutical compositions containing same.

  本发明提供了一种制备苯甲基取代的罗达宁衍生物的新型过程。该过程特别适用于合成这些衍生物的对映体。此外，还提供了新型苯甲基取代的巯基丙酸和苯甲基取代的噻唑烷酮。这些化合物对治疗炎症性肠病有用，因此，本发明提供了一种利用这种新型化合物以及含有相同化合物的药物组合物来治疗哺乳动物的炎症性肠病的方法。