1-(4-羟基-2-甲基苯基)丁烷-1-酮 | 104174-31-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(4-羟基-2-甲基苯基)丁烷-1-酮
• 英文名称: 1-(4-hydroxy-2-methylphenyl)butane-1-one
• 英文别名: 1-(4-hydroxy-2-methyl-phenyl)-butan-1-one；1-(4-Hydroxy-2-methyl-phenyl)-butan-1-on；1-(4-Hydroxy-2-methylphenyl)butan-1-one；1-(4-hydroxy-2-methylphenyl)butan-1-one
• CAS: 104174-31-4
• 化学式: C₁₁H₁₄O₂
• 分子量: 178.231
• InChiKey: YYBLGHXMEUSNLA-UHFFFAOYSA-N

物化性质

• 熔点：
  88 °C
• 沸点：
  142-144 °C(Press: 15 Torr)
• 密度：
  1.056±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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-(4-羟基-2-甲基苯基)丁烷-1-酮 在 四甲基乙二胺 、 potassium tert-butylate 、 potassium iodide 作用下， 以 四氢呋喃 为溶剂， 反应 85.0h， 生成 ethyl (3-methyl-4-(2-methylenebutyryl)phenoxy)acetate
  参考文献：
  名称：

  A New Lead for Nonpeptidic Active-Site-Directed Inhibitors of the Severe Acute Respiratory Syndrome Coronavirus Main Protease Discovered by a Combination of Screening and Docking Methods

  摘要：

  The coronavirus main protease, M-pro, is considered to be a major target for drugs suitable for combating coronavirus infections including severe acute respiratory syndrome (SARS). An HPLC-based screening of electrophilic compounds that was performed to identify potential M-pro inhibitors revealed etacrynic acid tert-butylamide (6a) as an effective nonpeptidic inhibitor. Docking studies suggested a binding mode in which the phenyl ring acts as a spacer bridging the inhibitor's activated double bond and its hydrophobic tert-butyl moiety. The latter is supposed to fit into the S4 pocket of the target protease. Furthermore, these studies revealed etacrynic acid amide (6b) as a promising lead for nonpeptidic active-site-directed M-pro inhibitors. In a fluorimetric enzyme assay using a novel fluorescence resonance energy transfer (FRET) pair labeled substrate, compound 6b showed a K-i value of 35.3 mu M. Since the novel lead compound does not target the S1', S1, and S2 subsites of the enzyme's substrate-binding pockets, there is room for improvement that underlines the lead character of compound 6b.

  DOI：

  10.1021/jm0501782
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 三氯化铝 、 氯苯 作用下， 生成 1-(4-羟基-2-甲基苯基)丁烷-1-酮
  参考文献：
  名称：

  John; Beetz, Journal fur praktische Chemie (Leipzig 1954), 1937, vol. <2>149, p. 164,167

  摘要：

  DOI：

文献信息

• 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。
• Forest Biotechnology '99—A Joint Meeting of the International Wood Biotechnology Symposium and the Iufro Working Party for Molecular Genetics of Trees, 11–16 July, 1999 Oxford, UK
  作者：D. Ellis、T. Strabala

  DOI：10.1007/s11627-000-0027-1

  日期：2000.3

  Genetically Engineered Free Forests (GEFF), a group assembled specifically in response to the meeting. In addition, on the opening night of the meeting the only field trial of transgenic trees in the UK, testing trees engineered to suppress lignin production (CAD antisense), was destroyed. The meeting opened with a keynote address by Ron Sederoff (North Carolina University, USA) in which he succinctly

  在参加 1999 年首屈一指的森林生物技术会议时，有什么比每天走进一座巨大的玻璃屋顶大厦更好的方式来保持自己的视野，这是英格兰新哥特式建筑的最佳典范之一，却被古老的骨骼所耸立禽龙的遗骸，一种巨大的白垩纪恐龙。在前往会议室的路上必须经过的其他恐龙骨骼和恐龙蛋中，有一个展览为刘易斯卡罗尔创作《爱丽丝梦游仙境》提供了灵感，其中包含现存最完整的遗骸，头和脚，现已灭绝渡渡鸟。牛津大学自然历史博物馆于 1860 年 7 月举办了臭名昭著的威尔伯福斯和赫胥黎关于创造与进化的辩论，近 140 年后也是森林生物技术 '99 的所在地。会议的目的是提供一个论坛，展示分子生物学和遗传学在林木中应用的最新进展。来自 30 个国家的 200 多名科学家分享了重点关注森林树种的信息，涵盖了广泛的主题，包括体外培养、基因工程、发育、适应性和生理性状的分子分析、细胞壁生物合成和修饰，以及基因组学和基因组图谱。就像 19
• XLII.—The variation of phenol coefficients in homologous series of phenols
  作者：Charles Edward Coulthard、Joseph Marshall、Frank Lee Pyman

  DOI：10.1039/jr9300000280

  日期：——
• The Mechanisms of the Fries Reaction¹
  作者：Richard Baltzly、Walter S. Ide、Arthur P. Phillips

  DOI：10.1021/ja01614a049

  日期：1955.5
• Über die Darstellung von Isonitrosoketonen
  作者：Erwin Karg

  DOI：10.1002/ardp.19442820108

  日期：——