1-(2-羟基-4-甲基苯基)丙烷-1-酮 | 2886-52-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(2-羟基-4-甲基苯基)丙烷-1-酮
• 英文名称: 1-(2-hydroxy-4-methyl-phenyl)-propan-1-one
• 英文别名: 1-(2-hydroxy-4-methylphenyl)propan-1-one；2-hydroxy-4-methylpropiophenone；1-(2-Hydroxy-4-methyl-phenyl)-propan-1-on；2-Hydroxy-4-methyl-propiophenon；3-Methyl-6-propionyl-phenol；6-Propionyl-3-methyl-phenol
• CAS: 2886-52-4
• 化学式: C₁₀H₁₂O₂
• mdl: MFCD00218575
• 分子量: 164.204
• InChiKey: PDHADLNZFCPLIV-UHFFFAOYSA-N

物化性质

• 熔点：
  44°C
• 沸点：
  251.67°C (rough estimate)
• 密度：
  1.0326 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-羟基-4-甲基苯基)丙烷-1-酮 在 氢氧化钾 、 盐酸羟胺 作用下， 以 乙醇 为溶剂， 以40%的产率得到2-hydroxy-4-methylpropiophenone oxime
  参考文献：
  名称：

  Jhaveri, L.C.; Naik, H.B.; Patel, G.S., Journal of the Indian Chemical Society, 1980, vol. 57, # 10, p. 1027 - 1028

  摘要：

  DOI：
• 作为产物：
  描述：

  3-甲基-2-丙-2-基苯酚 在 三氯化铝 作用下， 以 硝基甲烷 为溶剂， 反应 172.0h， 生成 1-(2-羟基-4-甲基苯基)丙烷-1-酮
  参考文献：
  名称：

  Lewis acids catalysed Fries rearrangement of isopropylcresol esters

  摘要：

  DOI：

  10.1007/bf00809536

文献信息

• Photoredox/nickel-catalyzed hydroacylation of ethylene with aromatic acids
  作者：Lili Zhang、Shuai Chen、Hengchi He、Weipeng Li、Chengjian Zhu、Jin Xie

  DOI：10.1039/d1cc04188f

  日期：——

  We report a general, practical and scalable hydroacylation reaction of ethylene with aromatic carboxylic acids with the synergistic combination of nickel and photoredox catalysis. Under ambient temperature and pressure, feedstock chemicals such as ethylene can be converted into high-value-added aromatic ketones in moderate to good yields (up to 92%) with reaction time of 2–6 hours.

  我们报告了乙烯与芳香族羧酸在镍和光氧化还原催化的协同组合下的通用、实用和可扩展的加氢酰化反应。在环境温度和压力下，原料化学品，如乙烯可在中等至良好的产率（高达92％），用2反应时间被转化成高附加值的芳香族酮- 6小时。
• Comparisons of O-acylation and Friedel–Crafts acylation of phenols and acyl chlorides and Fries rearrangement of phenyl esters in trifluoromethanesulfonic acid: effective synthesis of optically active homotyrosines
  作者：Ryo Murashige、Yuka Hayashi、Syo Ohmori、Ayuko Torii、Yoko Aizu、Yasuyuki Muto、Yuta Murai、Yuji Oda、Makoto Hashimoto

  DOI：10.1016/j.tet.2010.11.047

  日期：2011.1

  Reactions involving phenol derivatives and acyl chlorides have to be controlled for competitive O-acylations and C-acylations (Friedel–Crafts acylations and Fries rearrangements) in acidic condition. The extent for these reactions in trifluoromethanesulfonic acid (TfOH), which is used as catalyst and solvent, is examined. Although diluted TfOH was needed for effective O-acylation, concentrated TfOH

  对于酸性条件下的竞争性O-酰化和C-酰化（Friedel-Crafts酰化和Fries重排），必须控制涉及酚衍生物和酰氯的反应。检查了在用作催化剂和溶剂的三氟甲磺酸（TfOH）中这些反应的程度。尽管有效的O-酰化需要稀释的TfOH，但在温和的条件下有效的C-酰化则需要浓缩的TfOH。这些结果已应用于新的高酪氨酸衍生物的合成。N -TFA–Asp（OBn）–OMe的弗里斯重排和苯酚与N的Friedel-Crafts酰化反应TfOH中的-TFA–Asp（Cl）–OMe提供高酪氨酸骨架，然后还原和脱保护得到高酪氨酸，以光学纯净形式保留Asp的立体化学。
• Broadening the catalyst and reaction scope of regio- and chemoselective C–H oxygenation: a convenient and scalable approach to 2-acylphenols by intriguing Rh(ii) and Ru(ii) catalysis
  作者：Gang Shan、Xuesong Han、Yun Lin、Shanyou Yu、Yu Rao

  DOI：10.1039/c3ob27457h

  日期：——

  catalyzed C–H oxygenation of aryl ketones and other arenes has been developed for the facile synthesis of diverse functionalized phenols. The reaction demonstrates excellent reactivity, regio- and chemoselectivity, good functional group compatibility and high yields. The practicality of this method has been proved by gram-scale synthesis of a few different 2-acylphenols. Its utility has been well exemplified

  已开发出一种独特的Rh（II）和Ru（II）催化的芳基酮和其他芳烃的CH氧化反应，可以轻松合成各种功能化的酚。该反应显示出优异的反应性，区域和化学选择性，良好的官能团相容性和高产率。该方法的实用性已通过克级合成几种不同的2-酰基酚得到了证明。它的效用已在杂环合成和药物的直接修饰中的进一步应用中得到很好的例证非诺贝特。
• CONSTRUCTION AND SCREENING OF SOLUTION-PHASE DERIVED LIBRARY OF FENBUFEN AND ETHACRYNIC ACID
  申请人：Yu Chung-Shan

  公开号：US20110306668A1

  公开（公告）日：2011-12-15

  A process for synthesizing and screening solution phase derived libraries of fenbufen and ethacrynic acid is provided in the present invention. Compounds in the present invention having cytotoxicities are useful for a variety of therapeutic applications.

  本发明提供了一种合成和筛选溶液相衍生的芬布芬和依他克酸库的过程。本发明中具有细胞毒性的化合物对多种治疗应用是有用的。
• Facile access to novel chromeno-2,6,9-trioxabicyclo[3.3.1]nonadienes via tandem nucleophilic substitution and [4+2] hetero Diels–Alder reaction: experimental and theoretical study
  作者：Satyanarayana Reddy Jaggavarapu、Anand Solomon Kamalakaran、Gaddamanugu Gayatri、Matsyendranath Shukla、Kavita Dorai、Gopikrishna Gaddamanugu

  DOI：10.1016/j.tet.2013.01.002

  日期：2013.3

  An efficient synthesis of novel chromeno-2,6,9-trioxabicyclo-[3.3.1]nonadienes (CTOBN) scaffolds was achieved by mild base mediated reaction of 4-chloro-3-formylcoumarin and o-hydroxyacetophenones. The structure of the product was confirmed by X-ray analysis and the proposed mechanism was validated computationally at B3LYP/6-31G(d) level.

  通过4-氯-3-甲酰基香豆素和邻羟基苯乙酮的轻度碱介导反应，可以有效合成新型的chromeno-2,6,9-三恶双环-[3.3.1]壬二烯（CTOBN）支架。通过X射线分析确定了产品的结构，并在B3LYP / 6-31G（d）水平上对所提出的机理进行了计算验证。