5-hydroxy-2-(phenylthiomethyl)-4H-pyran-4-one | 138426-83-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 5-hydroxy-2-(phenylthiomethyl)-4H-pyran-4-one
• 英文别名: 5-Hydroxy-2-(phenylsulfanylmethyl)pyran-4-one
• CAS: 138426-83-2
• 化学式: C₁₂H₁₀O₃S
• mdl: MFCD08531027
• 分子量: 234.276
• InChiKey: HOVLWGFSEOFXSR-UHFFFAOYSA-N

物化性质

• 沸点：
  427.2±45.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.083
• 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：

  5-hydroxy-2-(phenylthiomethyl)-4H-pyran-4-one 在 Oxone 作用下， 以 甲醇 、 水 为溶剂， 生成 5-hydroxy-2-((phenylsulfonyl)methyl)-4H-pyran-4-one
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Kojyl Thioether Derivatives as Tyrosinase Inhibitors

  摘要：

  DOI：

  10.5012/bkcs.2010.31.8.2375
• 作为产物：
  描述：

  曲酸 在 氯化亚砜 、 sodium methylate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 6.0h， 生成 5-hydroxy-2-(phenylthiomethyl)-4H-pyran-4-one
  参考文献：
  名称：

  Discovery of 4-oxo-6-((pyrimidin-2-ylthio)methyl)-4H-pyran-3-yl 4-nitrobenzoate (ML221) as a functional antagonist of the apelin (APJ) receptor

  摘要：

  The recently discovered apelin/APJ system has emerged as a critical mediator of cardiovascular homeostasis and is associated with the pathogenesis of cardiovascular disease. A role for apelin/APJ in energy metabolism and gastrointestinal function has also recently emerged. We disclose the discovery and characterization of 4-oxo-6-((pyrimidin-2-ylthio)methyl)-4H-pyran-3-yl 4-nitrobenzoate (ML221), a potent APJ functional antagonist in cell-based assays that is >37-fold selective over the closely related angiotensin II type 1 (AT1) receptor. ML221 was derived from an HTS of the similar to 330,600 compound MLSMR collection. This antagonist showed no significant binding activity against 29 other GPCRs, except to the kappa-opioid and benzodiazepinone receptors (<50/<70%I at 10 mu M). The synthetic methodology, development of structure-activity relationship (SAR), and initial in vitro pharmacologic characterization are also presented. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.105

文献信息

• C₂-Symmetric Chiral Squaramide, Recyclable Organocatalyst for Asymmetric Michael Reactions
  作者：Alexander S. Kucherenko、Alexey A. Kostenko、Andrey N. Komogortsev、Boris V. Lichitsky、Michael Yu. Fedotov、Sergei G. Zlotin

  DOI：10.1021/acs.joc.9b00252

  日期：2019.4.5

  organocatalyst for asymmetric Michael reactions has been elaborated. In the presence of only 1 mol % of this catalyst, kojic acid derivatives and β-dicarbonyl compounds reacted with nitroolefins, affording the corresponding adducts in a nearly quantitative yield with an enantioselectivity up to 99% ee. The kojic acid-derived adducts could be efficiently produced under “green” conditions (in 96% EtOH or

  一个非常简单且高效的C 2阐述了用于不对称迈克尔反应的不对称叔胺-方酸酰胺有机催化剂。在仅1mol％的该催化剂的存在下，曲酸衍生物和β-二羰基化合物与硝基烯烃反应，以接近定量的产率提供相应的加合物，对映选择性高达99％ee。曲酸衍生的加合物可以在“绿色”条件下（在96％乙醇或纯水中）有效生产。而且，由于在有机溶剂中的溶解度非常低，因此可以容易地回收开发的无载体催化剂，并将其重复使用多达7次用于催化反应。极高的可用性（无需色谱纯化即可进行一步合成），高水平的立体诱导，低有效负载和可回收性，使其在制药行业的工业应用中具有吸引力。
• The first example of cine-substitution for 3-nitrocoumarins. Effective approach to the synthesis of 2H-chromen-2-ones containing 3-hydroxypyran-4-one fragment
  作者：Andrey N. Komogortsev、Boris V. Lichitsky、Valeriya G. Melekhina、Mikhail E. Minyaev

  DOI：10.1016/j.tetlet.2021.152939

  日期：2021.3

  For the first time we have demonstrated the feasibility of cine-substitution for 3-nitrocoumarins. Based on this process a novel efficient one-step protocol for the preparation of substituted 2H-chromen-2-ones bearing 3-hydroxypyran-4-one moiety has been developed. The presented method includes base-catalyzed reaction of allomaltol derivatives with various 3-nitrocoumarins. The reaction proceeds under

  我们首次证明了用电影代替3-硝基香豆素的可行性。基于该方法，已经开发了一种新颖的有效的一步方案，用于制备带有3-羟基吡喃-4-酮部分的取代的2 H-色烯-2-酮。提出的方法包括异麦芽酚衍生物与各种3-硝基香豆素的碱催化反应。反应在温和的条件下进行，使用简单的纯化程序即可轻松获得产物。通过X射线衍射确定了2 H-铬-2--2-酮衍生物之一的结构。
• Asymmetric Michael addition between kojic acid derivatives and unsaturated ketoesters promoted by <i>C</i>₂-symmetric organocatalysts
  作者：Alexey A. Kostenko、Alexander S. Kucherenko、Andrey N. Komogortsev、Boris V. Lichitsky、Sergei G. Zlotin

  DOI：10.1039/c8ob02523a

  日期：——

  An efficient sterically hindered C2-symmetric bifunctional tertiary amine–squaramide organocatalyst for the asymmetric Michael addition/hemiketalization domino reaction of kojic acid derivatives with β,γ-unsaturated α-ketoesters has been designed. Pharmacology-relevant functionalized 2,3,4,8-tetrahydropyrano[3,2-b]pyran derivatives were produced over the catalyst in as low as 1 mol% with up to 99%

  设计了一种高效的位阻C 2对称双官能叔胺-方酰胺有机催化剂，用于曲酸衍生物与β，γ-不饱和α-酮酸酯的不对称迈克尔加成/半缩酮化多米诺反应。在催化剂上以低至1 mol％的产率制备了药理学相关的官能化2,3,4,8-四氢吡喃并[3,2- b ]吡喃衍生物，产率高达99％，ee高达99％。该程序至少可扩展30倍，并且该催化剂可通过酸碱萃取容易地用于催化反应中。用（S）-或rac酰化产物-布洛芬和十一碳烯酸与相应的手性酯含有两个特权药效基序。
• Hydroxy-directed iridium-catalyzed enantioselective formal β-C(sp²)–H allylic alkylation of α,β-unsaturated carbonyls
  作者：Sankash Mitra、Rahul Sarkar、Aditya Chakrabarty、Santanu Mukherjee

  DOI：10.1039/d2sc03966d

  日期：——

  Hydroxy-directed iridium-catalyzed enantioselective formal β-C(sp2)–H allylic alkylation of kojic acid and structurally related α,β-unsaturated carbonyl compounds is developed. This reaction, catalyzed by an Ir(I)/(P,olefin) complex, utilizes the nucleophilic character of α-hydroxy α,β-unsaturated carbonyls, to introduce an allyl group at its β-position in a branched-selective manner in good to excellent

  开发了羟基导向的铱催化的对映选择性形式 β-C(sp 2 )–H 烯丙基烷基化曲酸和结构相关的 α,β-不饱和羰基化合物。该反应由 Ir( I )/( P ,olefin) 络合物催化，利用 α-羟基 α,β-不饱和羰基的亲核特性，以支化选择性方式在其 β-位引入烯丙基良好至优异的产率，具有一致的高对映选择性（高达 >99.9 : 0.1 er）。据我们所知，这份报告代表了在过渡金属催化的高度对映选择性转化中使用曲酸的第一个例子。
• Inhibitory Activities of Kojyl Thioether Derivatives against Nitric Oxide Production Induced by Lipopolysaccharide
  作者：Ho-Sik Rho、Dae-Sung Yoo、Soo-Mi Ahn、Myung-Kyoo Kim、Dong-Ha Cho、Jae-Youl Cho

  DOI：10.5012/bkcs.2010.31.11.3463

  日期：2010.11.20