2-methyl-4-(2,5-dimethoxyphenyl)-3-butyn-2-ol | 22944-10-1

• 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: 2-methyl-4-(2,5-dimethoxyphenyl)-3-butyn-2-ol
• 英文别名: 1-(2,5-Dimethoxyphenyl)-3-hydroxy-3-methyl-1-butin；4-(2,5-Dimethoxyphenyl)-2-methyl-3-butyn-2-ol；4-(2,5-dimethoxyphenyl)-2-methylbut-3-yn-2-ol
• CAS: 22944-10-1
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: NOGFYASJSONHDS-UHFFFAOYSA-N

物化性质

• 沸点：
  140-145 °C(Press: 0.18 Torr)
• 密度：
  1.11±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：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-methyl-4-(2,5-dimethoxyphenyl)-3-butyn-2-ol 在 溴苯 、 [Cp*RhCl₂]2 、 三(1-萘基)膦 、 palladium diacetate 、 caesium carbonate 、 silver carbonate 作用下， 以 邻二甲苯 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成
  参考文献：
  名称：

  强大的抗炎药Sparstolonin B的全合成†

  摘要：

  已经描述了两种简捷的路线，用于第一次全面合成Sparstolonin B（SsnB）。SsnB的合成可以分5步和6步完成，总产率分别为40％和38％。两种策略均使用铑催化的苯甲酸与内部炔烃的氧化偶联来构建SsnB的核心结构。

  DOI：

  10.1039/c4ra15948a
• 作为产物：
  描述：

  1-溴-2,5-二甲氧基苯 、 2-甲基-3-丁炔-2-醇 在 哌啶 、 copper(l) iodide 、 三苯基膦 、 palladium dichloride 作用下， 反应 12.0h， 以90%的产率得到2-methyl-4-(2,5-dimethoxyphenyl)-3-butyn-2-ol
  参考文献：
  名称：

  强大的抗炎药Sparstolonin B的全合成†

  摘要：

  已经描述了两种简捷的路线，用于第一次全面合成Sparstolonin B（SsnB）。SsnB的合成可以分5步和6步完成，总产率分别为40％和38％。两种策略均使用铑催化的苯甲酸与内部炔烃的氧化偶联来构建SsnB的核心结构。

  DOI：

  10.1039/c4ra15948a

文献信息

• Preparation and characterisation of a quinone-functionalised polythiophene film on a modified electrode. Application to the potentiometric determination of glutathione and cysteine concentrations
  作者：Stéphanie Étienne、Muriel Matt、Thierry Oster、Mohammad Samadi、Marc Beley

  DOI：10.1016/j.tet.2008.07.041

  日期：2008.9

  The new compound 3-((2,5-dimethoxyphenyl)ethynyl)thiophene has been synthesised by Sonogashira coupling. A modified electrode coated with a polythiophene film hearing a quinone moiety was obtained by electropolymerisation of the thienyl group followed by anodic oxidation of para-dimethoxyphenyl group. The cyclovoltammetric response resulting from the reaction of glutathione with the benzoquinone moiety was investigated. The responses of the modified electrode as a new potentiometric sensor of reduced thiols are proposed. (C) 2008 Elsevier Ltd. All rights reserved.
• A Practical Synthesis of 6-[2-(2,5-Dimethoxyphenyl)ethyl]-4-ethylquinazoline and the Art of Removing Palladium from the Products of Pd-Catalyzed Reactions
  作者：Kurt Königsberger、Guang-Pei Chen、Raeann R. Wu、Michael J. Girgis、Kapa Prasad、Oljan Repič、Thomas J. Blacklock

  DOI：10.1021/op034072x

  日期：2003.9.1

  A concise large-scale synthesis of 1, a new antimitotic agent is described. The key step was a one-pot Sonogashira cross-coupling of an aryl halide with a heteroaryl halide through an acetylene using the readily available 2-methyl-3-butyn-2-ol (7). An innovative approach for palladium removal was designed and successfully scaled-up on a multikilogram scale. The product was crystallized from the crude reaction mixture while keeping the residual palladium in the mother liquor by using Pd-scavenging agents such as N-acetylcysteine or thiourea.
• Electrophilic Cyclization of 2-Chalcogenealkynylanisoles: Versatile Access to 2-Chalcogen-benzo[<i>b</i>]furans
  作者：Flávia Manarin、Juliano A. Roehrs、Rafaela Mozzaquatro Gay、Ricardo Brandão、Paulo H. Menezes、Cristina W. Nogueira、Gilson Zeni

  DOI：10.1021/jo802736e

  日期：2009.3.6

  An efficient synthesis of 2-chalcogen-3-substituted-benzo[b]furan compounds has been accomplished via electrophilic cyclization reaction of 2-chalcogenealkynyl anisoles using I-2, ICl, Br-2 and PhSeBr as electrophile sources. The product distributions were strongly dependent on the nature of substituents in the aromatic ring of anisole and on the chalcogen atom directly bonded to the triple bond. The 2-chalcogen-3-iodo-benzo[b]furans obtained smoothly underwent conversion to more complex structures of benzo[b]furan derivatives via palladium- or copper-catalyzed cross-coupling reaction with thiols, diphenyl diselenides, and zincates.