5-(3,5-Di-tert-butyl-4-oxocyclohexa-2,5-dien-1-ylidene)-1,3,4-oxathiazolidin-2-one | 114522-42-8

• 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-Di-tert-butyl-4-oxocyclohexa-2,5-dien-1-ylidene)-1,3,4-oxathiazolidin-2-one
• 英文别名: 5-(3,5-ditert-butyl-4-hydroxyphenyl)-1,3,4-oxathiazol-2-one
• CAS: 114522-42-8
• 化学式: C₁₆H₂₁NO₃S
• 分子量: 307.414
• InChiKey: DWWNMIPPHGZAHO-UHFFFAOYSA-N

物化性质

• 沸点：
  374.0±52.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  84.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(3,5-Di-tert-butyl-4-oxocyclohexa-2,5-dien-1-ylidene)-1,3,4-oxathiazolidin-2-one 以 甲醇 为溶剂， 反应 19.0h， 生成 2,6-bis(1,1-dimethylethyl)-4-(5-methylthio-1,2,4-thiadiazol-3-yl)phenol
  参考文献：
  名称：

  通过与4-甲基苯磺酰基氰化物（甲苯磺酰基氰化物）环化制备新型1,2,4-噻二唑†

  摘要：

  描述了在噻二唑3-位带有二叔丁基苯酚取代基的1,2,4-噻二唑的制备。在1，3-偶极环化反应中，使热产生的腈硫化物与甲苯磺酰基氰化物反应，以提供含有不稳定的5-甲苯磺酰基取代基的噻二唑中间体。

  DOI：

  10.1002/jhet.5570300211
• 作为产物：
  描述：

  3,5-二-叔-丁基-4-羟基苯甲酰胺 、 氯羰基亚磺酰氯 在 Toluene heptane 作用下， 生成 5-(3,5-Di-tert-butyl-4-oxocyclohexa-2,5-dien-1-ylidene)-1,3,4-oxathiazolidin-2-one
  参考文献：
  名称：

  Substituted 1,3,4-oxathiazol-2-one stabilizers

  摘要：

  该文献描述了一种公式为##STR1## 的1,3,4-氧硫杂唑-2-酮衍生物以及有机材料。通过在有机材料中添加该衍生物，可以使其稳定性得到提高，抵抗氧化、热降解和光降解。

  公开号：

  US04724246A1

文献信息

• Non-ATP competitive glycogen synthase kinase 3β (GSK-3β) inhibitors: Study of structural requirements for thiadiazolidinone derivatives
  作者：Ana Castro、Arantxa Encinas、Carmen Gil、Stefan Bräse、Williams Porcal、Concepción Pérez、Francisco J. Moreno、Ana Martínez

  DOI：10.1016/j.bmc.2007.09.016

  日期：2008.1

  The 2,4-disubstituted thiadiazolidinones (TDZD) were described as the first non-ATP competitive GSK-3 beta inhibitors. New modifications in this heterocyclic ring are here reported to study the influence on the biological activity. The basic skeleton of 1,2,4-thiadiazole and also one of the carbonyl groups are kept, while different modifications are introduced in positions 3 and 5, respectively. The GSK-3 beta activity of the new thiadiazole derivatives here synthesized showed IC50 values for some of the compounds in the micromolar range. Additionally, ATP competition studies have been carried out, showing that as well as the first generation of TDZD, these new compounds act in a non-competitive manner. With this study, additional requirements for the biological activity of the TDZD family have been delineated. (c) 2007 Elsevier Ltd. All rights reserved.
• Heteroarylnitrones as Drugs for Neurodegenerative Diseases: Synthesis, Neuroprotective Properties, and Free Radical Scavenger Properties
  作者：Williams Porcal、Paola Hernández、Mercedes González、Ana Ferreira、Claudio Olea-Azar、Hugo Cerecetto、Ana Castro

  DOI：10.1021/jm8006432

  日期：2008.10.9

  New 1,2,4-thiadiazolylnitrones and furoxanylnitrones were developed and evaluated as neuroprotective agents on a human neuroblastoma (SH-SY5Y) cells model. They inhibited at low micromolar concentrations the oxidative damage and the death induced by exposure to hydrogen peroxide. These heteroarylnitrones showed excellent peroxyl free radical absorbance capacities, analyzed by oxygen radical absorbance capacity (ORAC) assay with fluorescein as the fluorescent probe, ranging from 1.5- to 16.5-fold the value of the reference nitrone, alpha-phenyl-N-tert-butylnitrone (PBN). The electron spin resonance spectroscopy (ESR) demonstrated the ability of these derivatives to directly trap and stabilize oxygen, carbon, and sulfur-centered free radicals. These results demonstrated the potential use of these heteroarylnitrones as neuroprotective agents in preventing the death of cells exposed to enhanced oxidative stress and damage.
• US4724246A
  申请人：——

  公开号：US4724246A

  公开（公告）日：1988-02-09
• Preparation of novel 1,2,4-thiadiazoles by cyclization with 4-methylbenzenesulfonyl cyanide (tosyl cyanide)
  作者：Paul C. Unangst、Gary P. Shrum、David T. Connor

  DOI：10.1002/jhet.5570300211

  日期：1993.3

  The preparation of 1,2,4-thiadiazoles with a di-tert-butylphenol substituent at the thiadiazole 3-position is described. A thermally generated nitrile sulfide was reacted with tosyl cyanide in a 1,3-dipolar cyclization reaction to provide a thiadiazole intermediate containing a labile 5-tosyl substituent.

  描述了在噻二唑3-位带有二叔丁基苯酚取代基的1,2,4-噻二唑的制备。在1，3-偶极环化反应中，使热产生的腈硫化物与甲苯磺酰基氰化物反应，以提供含有不稳定的5-甲苯磺酰基取代基的噻二唑中间体。
• Substituted 1,3,4-oxathiazol-2-one stabilizers
  申请人：Ciba-Geigy Corporation

  公开号：US04724246A1

  公开（公告）日：1988-02-09

  Substituted 1,3,4-oxathiazol-2-one derivatives of the formula ##STR1## and organic materials stabilized against oxidative, thermal and/or actinic degradation by the presence therein of said derivatives.

  该文献描述了一种公式为##STR1## 的1,3,4-氧硫杂唑-2-酮衍生物以及有机材料。通过在有机材料中添加该衍生物，可以使其稳定性得到提高，抵抗氧化、热降解和光降解。