ethyl phenyl [4-(hydroxyphenyl)sulfanyl]acetate | 287393-39-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: ethyl phenyl [4-(hydroxyphenyl)sulfanyl]acetate
• 英文别名: ethyl phenyl [(4-hydroxyphenyl)sulfanyl] acetate；ethyl phenyl[4-(hydroxyphenyl)sulfanyl]acetate；Ethyl 2-(4-hydroxyphenyl)sulfanyl-2-phenylacetate
• CAS: 287393-39-9
• 化学式: C₁₆H₁₆O₃S
• 分子量: 288.367
• InChiKey: FOCKFGZKFJCPRB-UHFFFAOYSA-N

物化性质

• 沸点：
  433.3±45.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  71.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl phenyl [4-(hydroxyphenyl)sulfanyl]acetate 在 Oxone 、 sodium hydroxide 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 丙酮 为溶剂， 生成 {[4-(2-butynyloxy)phenyl]sulfonyl}(phenyl)acetic acid
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of 4-alkynyloxy Phenyl Sulfanyl, Sulfinyl, and Sulfonyl Alkyl Hydroxamates as Tumor Necrosis Factor-α Converting Enzyme and Matrix Metalloproteinase Inhibitors

  摘要：

  A series of 4-alkynyloxy phenyl sulfanyl, sulfinyl and sulfony alkyl and piperidine-4-carboxylic acid hydroxamides were synthesized. Their structure-activity relationships, against tumor necrosis factor-alpha (TACE) and matrix metalloproteinase (NIMP) inhibitor activities, are presented by investigating the oxidation state on sulfur and altering the P1' substituent. The sulfonyl derivatives 20-24 carrying a 4-butynyloxy moiety were selective TACE inhibitors over the MMPs tested. The sulfinyl derivatives showed a preference for a specific oxidation on sulfur as in compounds 25-28. The selectivity over MMPs was also demonstrated in the sulfonyl series. The enhanced cellular activity was achieved upon incorporating a butynyloxy substituent in the piperidene series. Compounds 64 and 65 were potent inhibitors of TNF-alpha release in the mouse at 100 mg/kg po.

  DOI：

  10.1021/jm040086x
• 作为产物：
  描述：

  4-羟基苯硫酚 、 ethyl 2-(dimethyl(oxo)- λ⁶-sulfaneylidene)-2-phenylacetate 以 乙腈 为溶剂， 反应 24.0h， 以80%的产率得到ethyl phenyl [4-(hydroxyphenyl)sulfanyl]acetate
  参考文献：
  名称：

  钯催化合成双取代的ox硫鎓叶立德

  摘要：

  通过开发一种钯催化的α-酯sulf氧化物与（杂）芳基碘化物，溴化物和三氟甲磺酸酯的C–H交叉偶联，可以解决一般无法获得双取代sulf氧化物的问题。已经评估了三种不同的催化剂。该方法适合于活性药物成分的后期功能化。

  DOI：

  10.1021/acs.orglett.8b03744

文献信息

• Alkynyl containing hydroxamic acid compounds as matrix metalloproteinase and tace inhibitors
  申请人：American Cyanamid Company

  公开号：US06340691B1

  公开（公告）日：2002-01-22

  Compounds of the formula are useful in treating disease conditions mediated by TNF-&agr;, such as rheumatoid arthritis, osteoarthritis, sepsis, AIDS, ulcerative colitis, multiple sclerosis, Crohn's disease and degenerative cartilage loss.

  该公式的化合物可用于治疗由TNF-α介导的疾病状况，例如类风湿性关节炎、骨关节炎、脓毒症、艾滋病、溃疡性结肠炎、多发性硬化症、克罗恩病和退化性软骨丧失。
• Synthesis and Structure−Activity Relationships of 4-alkynyloxy Phenyl Sulfanyl, Sulfinyl, and Sulfonyl Alkyl Hydroxamates as Tumor Necrosis Factor-α Converting Enzyme and Matrix Metalloproteinase Inhibitors
  作者：Aranapakam M. Venkatesan、Jamie M. Davis、George T. Grosu、Jannie Baker、Arie Zask、Jeremy I. Levin、John Ellingboe、Jerauld S. Skotnicki、John F. DiJoseph、Amy Sung、Guixian Jin、Weixin Xu、Diane Joseph McCarthy、Dauphine Barone

  DOI：10.1021/jm040086x

  日期：2004.12.1

  A series of 4-alkynyloxy phenyl sulfanyl, sulfinyl and sulfony alkyl and piperidine-4-carboxylic acid hydroxamides were synthesized. Their structure-activity relationships, against tumor necrosis factor-alpha (TACE) and matrix metalloproteinase (NIMP) inhibitor activities, are presented by investigating the oxidation state on sulfur and altering the P1' substituent. The sulfonyl derivatives 20-24 carrying a 4-butynyloxy moiety were selective TACE inhibitors over the MMPs tested. The sulfinyl derivatives showed a preference for a specific oxidation on sulfur as in compounds 25-28. The selectivity over MMPs was also demonstrated in the sulfonyl series. The enhanced cellular activity was achieved upon incorporating a butynyloxy substituent in the piperidene series. Compounds 64 and 65 were potent inhibitors of TNF-alpha release in the mouse at 100 mg/kg po.
• Palladium-Catalyzed Synthesis of Bis-Substituted Sulfoxonium Ylides
  作者：Christopher Janot、Pierre Palamini、Benjamin C. Dobson、James Muir、Christophe Aïssa

  DOI：10.1021/acs.orglett.8b03744

  日期：2019.1.4

  The lack of general access to bis-substituted sulfoxonium ylides is addressed by developing a palladium-catalyzed C–H cross-coupling of α-ester sulfoxonium ylides with (hetero)aryl iodides, bromides, and triflates. Three different catalysts have been evaluated. This method is amenable to the late-stage functionalization of active pharmaceutical ingredients.

  通过开发一种钯催化的α-酯sulf氧化物与（杂）芳基碘化物，溴化物和三氟甲磺酸酯的C–H交叉偶联，可以解决一般无法获得双取代sulf氧化物的问题。已经评估了三种不同的催化剂。该方法适合于活性药物成分的后期功能化。