2-甲基-4-(2-(甲硫基)苯基)丁-3-炔-2-醇 | 124153-79-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 中文名称: 2-甲基-4-(2-(甲硫基)苯基)丁-3-炔-2-醇
• 英文名称: 2-methyl-4-(2-(methylthio)phenyl)but-3-yn-2-ol
• 英文别名: 2-Methyl-4-(2-methylsulfanylphenyl)but-3-yn-2-ol
• CAS: 124153-79-3
• 化学式: C₁₂H₁₄OS
• 分子量: 206.309
• InChiKey: DTQYREKYPUSEBC-UHFFFAOYSA-N

物化性质

• 沸点：
  322.4±27.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-甲基-4-(2-(甲硫基)苯基)丁-3-炔-2-醇 在 sodium hydride 作用下， 以 苯 为溶剂， 反应 1.0h， 以95%的产率得到1-乙炔基-2-(甲硫基)苯
  参考文献：
  名称：

  Synthesis and cyclooxygenase inhibitory activities of linear 1-(methanesulfonylphenyl or benzenesulfonamido)-2-(pyridyl)acetylene regioisomers

  摘要：

  A group of 1-(aminosulfonylphenyl and methylsulfonylphenyl)-2-(pyridyl) acetylene regioisomers were designed such that a COX-2 SO2NH2 pharmacophore was located at the para-position of the phenyl ring, or a SO2Me pharmacophore was placed at the ortho-, meta- or para-position of the phenyl ring, on an acetylene template (scaffold). The point of attachment of the pyridyl ring to the acetylene linker was simultaneously varied (2-pyridyl, 3-pyridyl, 4-pyridyl, 3-methyl- 2-pyridyl) to determine the combined effects of positional, steric, and electronic substituent properties upon COX-1 and COX-2 inhibitory potency and COX isozyme selectivity. These target linear 1-(phenyl)-2-(pyridyl) acetylenes were synthesized via a palladium-catalyzed Sonogashira cross-coupling reaction. Structure-activity relationship (SAR) data (IC50 values) acquired by determination of the in vitro ability of the title compounds to inhibit the COX-1 and COX-2 isozymes showed that the position of the COX-2 SO2NH2 or SO2Me pharmacophore on the phenyl ring, and the point of attachment of the pyridyl ring to the acetylene linker, were either individual, or collective, determinants of COX-2 inhibitory potency and selectivity. A number of compounds discovered in this study, particularly 1-(4-aminosulfonylphenyl)-2-(3-methyl-2-pyridyl) acetylene (22), 1-(3-methanesulfonylphenyl)-2-(2-pyridyl) acetylene (27), 1-(3methanesulfonylphenyl)-2-(4-pyridyl)acetylene (29), 1-(4-methanesulfonylphenyl)-2-(2-pyridyl)acetylene (30), and 1-(4-methanesulfonylphenyl)2-(3-pyridyl)acetylene (31), exhibit potent (IC50 = 0.04-0.33 mu M range) and selective (SI = 18 to > 312 range) COX-2 inhibitory activities, that compare favorably with the reference drug celecoxib (COX-2 IC50 = 0.07 mu M; COX-2 SI = 473). The sulfonamide (22), and methylsulfonyl (27 and 31), compounds exhibited anti-inflammatory activities (ID50 = 59.9-76.6 mg/kg range) that were intermediate in potency between the reference drugs aspirin (ID50 = 128.7 mg/kg) and celecoxib (ID50 = 10.8 mg/kg). (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.11.003
• 作为产物：
  描述：

  苯乙炔 在 正丁基锂 、 potassium tert-butylate 作用下， 反应 2.17h， 生成 2-甲基-4-(2-(甲硫基)苯基)丁-3-炔-2-醇
  参考文献：
  名称：

  Experimental and theoretical study of the dimetalation of phenylacetylene and (1-naphthyl)acetylene

  摘要：

  DOI：

  10.1021/jo00291a041

文献信息

• Synthesis and Evaluation of 3-Halobenzo[b]thiophenes as Potential Antibacterial and Antifungal Agents
  作者：Prerna J. Masih、Tanay Kesharwani、Elivet Rodriguez、Mia A. Vertudez、Mina L. Motakhaveri、Terelan K. Le、Minh Kieu T. Tran、Matthew R. Cloyd、Cory T. Kornman、Aimee M. Phillips

  DOI：10.3390/ph15010039

  日期：——

  with copper(II) sulfate. This environmentally benign methodology is facile, uses ethanol as the solvent, and results in 3-halo substituted benzo[b]thiophene structures in very high yields. The cyclohexanol-substituted 3-chloro and 3-bromobenzo[b]thiophenes resulted in a low MIC of 16 µg/mL against Gram-positive bacteria and yeast. Additionally, in silico absorption, distribution, metabolism, and excretion

  全球对抗菌素耐药性的健康关注已引起人们的研究兴趣，以寻找新类别的抗生素来对抗致病病原体。在我们的研究中，合成了3-卤代苯并[ b ]噻吩衍生物，并使用肉汤微量稀释药敏法测试了其抗菌活性。3-卤素取代的苯并[ b ]噻吩是从2-炔基茴香硫醚开始使用方便的亲电环化方法合成的，该方法利用卤化钠作为与硫酸铜(II)反应时的亲电卤素源。这种环境友好的方法很简单，使用乙醇作为溶剂，并以非常高的产率产生3-卤代苯并[ b ]噻吩结构。环己醇取代的 3-氯和 3-溴苯并[ b ]噻吩对革兰氏阳性细菌和酵母的 MIC 较低，为 16 µg/mL。此外，还确定了化合物的计算机吸收、分布、代谢和排泄 (ADME) 特性。具有最低 MIC 值的化合物表现出优异的类药特性，且不会违反 Lipinski、Veber 和 Muegge 过滤器的要求。获得了环己醇取代的3-氯苯并[ b ]噻吩对金黄色葡萄球菌的时间杀灭曲线，其在MIC下表现出快速杀菌活性。
• Synthesis of benzothienofuranones and dihydrobenzothienopyranones by palladium iodide-catalyzed carbonylative double cyclization
  作者：Ida Ziccarelli、Raffaella Mancuso、Domenico Santandrea、Angela Altomare、Diego Olivieri、Carla Carfagna、Bartolo Gabriele

  DOI：10.1016/j.jcat.2023.115101

  日期：2023.11

  second cyclization (possibly, through the formation of a palladacycle intermediate followed by reductive elimination), and Pd(0) reoxidation by oxygen (from air) used as external benign oxidant. Under similar conditions, 4-(2-(methylthio)phenyl)but-3-yn-1-ols, bearing a butynol moiety ortho to the methylthio group, led to a mixture of double cyclization and dicarbonylation products, however, by slightly

  3-(2-(甲硫基)苯基)丙-2-炔-1-醇已通过 PdI 在一个合成步骤中成功转化为苯并[4,5]噻吩并[2,3-c]呋喃-1-酮2 /KI 催化的氧化羰基化双环化过程，在相对温和的条件下（1–10 mol% PdI 2、7 当量的 KI、80 °C、60 atm 的 4:1 CO-空气混合物）在 MeCN 中进行。该过程通过一系列有序步骤进行，涉及 5- endo - dig S-环化，碘化物促进随后锍盐的去甲基化，CO插入，第二次环化（可能通过形成环环中间体，然后还原消除），以及用作外部氧气（来自空气）的Pd（0）再氧化良性氧化剂。在类似的条件下，4-(2-(甲硫基)苯基)丁-3-yn-1-醇，带有与甲硫基邻位的丁炔醇部分，导致双环化和二羰基化产物的混合物，然而，通过稍微调整在该反应条件下，可以选择性地获得二氢苯并[4,5]噻吩并[3,2-c]吡喃-1-酮，且不形成二羰基化副产物。四