1-(2-hydroxy-5-methyl-phenyl)-hexan-1-one | 101002-28-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2-hydroxy-5-methyl-phenyl)-hexan-1-one
• 英文别名: 1-(2-Hydroxy-5-methyl-phenyl)-hexan-1-on；1-(2-Hydroxy-5-methylphenyl)-1-hexanone；1-(2-hydroxy-5-methylphenyl)hexan-1-one
• CAS: 101002-28-2
• 化学式: C₁₃H₁₈O₂
• 分子量: 206.285
• InChiKey: OKLRXZMADIGFHP-UHFFFAOYSA-N

物化性质

• 沸点：
  163 °C(Press: 15 Torr)
• 密度：
  1.022±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 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-hydroxy-5-methyl-phenyl)-hexan-1-one 在 吡啶 、 盐酸羟胺 作用下， 生成 5-methyl-2-hydroxycaprophenone oxime
  参考文献：
  名称：

  Mass spectra of 1-(2′-hydroxy-5′-alkylphenyl)-1-alkanone (E)-oximes

  摘要：

  AbstractThe mass spectra of 1‐(2′‐hydroxy‐5′‐alkylphenyl)‐1‐ethanone (E)‐oximes 1–6 and 1‐(2′‐hydroxy‐5′‐methylphenyl)‐1‐alkanone (E)‐oximes 7–12 are given and the major fragmentation pathways discussed. The simultaneous loss of water and alkyl moieties from the molecular ion indicates that a skeletal rearrangement take place and a cycloheptatrienyloheterocyclic system is formed. The McLafferty rearrangement, γ‐fission in the side aliphatic chain and oxygen expulsion are discussed with evidence being drawn from accurate mass measurements, metastable ions and comparison with mass spectral data of related compounds.

  DOI：

  10.1002/oms.1210210108
• 作为产物：
  描述：

  己酰氯 在 四氯化碳 、 三氯化铝 作用下， 生成 1-(2-hydroxy-5-methyl-phenyl)-hexan-1-one
  参考文献：
  名称：

  The Preparation and Properties of Three Isomeric n-Hexyl Cresols and their Chlorinated Derivatives

  摘要：

  DOI：

  10.1021/ja01856a079

文献信息

• Rosenmund; Schnurr, Justus Liebigs Annalen der Chemie, 1928, vol. 460, p. 89
  作者：Rosenmund、Schnurr

  DOI：——

  日期：——
• 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：——
• Microwave-induced deactivation-free catalytic activity of BEA zeolite in acylation reactions
  作者：B.M. Chandra Shekara、B.S. Jai Prakash、Y.S. Bhat

  DOI：10.1016/j.jcat.2012.03.005

  日期：2012.6

  Solventless liquid-phase acylation of p-cresol with different aliphatic carboxylic acids like acetic, propionic, butyric, hexanoic, octanoic, and decanoic acids was investigated over BEA zeolite under conventional as well as microwave heating. An unanticipated huge difference in activity was observed between two modes of heating. Under conventional heating, conversion of all the acids was less than 20%, while under microwave heating, the conversion was in the range of 50-80%. Ester formed through O-acylation and ortho-hydroxyketone formed through Fries rearrangement of the ester were the only products. Conversion of carboxylic acid increased with chain length up to hexanoic acid and then it showed a decrease in the trend. With all the acids, O-acylation occurred rapidly followed by slow conversion to ortho-hydroxyketone. The ketone/ester ratio increased with catalyst amount, temperature, and reaction time. Used catalyst samples were characterized by TGA, XRD, and IR studies to understand lower activity and deactivation behavior under conventional heating. The results showed absence of coke precursor/coke on the catalyst used in microwave-irradiated reactions in contrast to catalyst used in conventionally heated ones. Higher yield in the case of microwave-assisted reactions is attributed to the prevention of coke precursor/coke on the active sites by microwaves. (c) 2012 Elsevier Inc. All rights reserved.