p-tolyl decanoate | 68367-32-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: p-tolyl decanoate
• 英文别名: p-cresyl decanoate；(4-Methylphenyl) decanoate
• CAS: 68367-32-8
• 化学式: C₁₇H₂₆O₂
• 分子量: 262.392
• InChiKey: VXLDTIULSUYHQY-UHFFFAOYSA-N

物化性质

• 沸点：
  175-178 °C(Press: 7 Torr)
• 密度：
  0.952±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  19
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  p-tolyl decanoate 在 三氯化铝 作用下， 生成 1-(2-羟基-5-甲基苯基)癸-1-酮
  参考文献：
  名称：

  Kawai et al., Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1956, vol. 76, p. 660,664

  摘要：

  DOI：
• 作为产物：
  描述：

  癸酰氯 在 4-二甲氨基吡啶 、 sodium sulfide 、 四丁基溴化铵 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 1.5h， 生成 p-tolyl decanoate
  参考文献：
  名称：

  二酰基二硫化物：4-（N，N-二甲基氨基）吡啶催化的苯酚化学选择性酰化试剂

  摘要：

  为了通过DMAP（4-（N，N-二甲基氨基）吡啶）催化实现有效的酯形成，发现了通用且优异的酰化试剂二酰基二硫化物。该方案为酚和伯脂族羟基的位点选择性酰化提供了一个有希望的合成平台，这大大扩展了保护基化学的领域。该试剂的重要性还体现在其出色的耐湿性，高效率以及在合成化学和生物学上有意义的天然产物修饰方面的潜力。

  DOI：

  10.1021/acs.orglett.6b02818

文献信息

• The active site accessibility aspect of montmorillonite for ketone yield in ester rearrangement
  作者：N. J. Venkatesha、B. S. Jai Prakash、Y. S. Bhat

  DOI：10.1039/c4cy01356e

  日期：——

  A new term Volume Accessibility Factor (VAF), the product of micropore volume and acidity, correlates with ketone formation in modified montmorillonite.

  一个新术语“体积可及性因子（VAF）”，是微孔体积和酸度的乘积，与改性蒙脱石中酮形成相关。
• Vijayakumar; Iyengar, Pushpa; Nagendrappa, Gopalpur, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2005, vol. 44, # 9, p. 1950 - 1953
  作者：Vijayakumar、Iyengar, Pushpa、Nagendrappa, Gopalpur、Prakash, B.S. Jai

  DOI：——

  日期：——
• Suresh Babu; Karanth; Divakar, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2002, vol. 41, # 5, p. 1068 - 1071
  作者：Suresh Babu、Karanth、Divakar

  DOI：——

  日期：——
• Active and deactive modes of modified montmorillonite in p-cresol acylation
  作者：N.J. Venkatesha、B.M. Chandrashekara、B.S. Jai Prakash、Y.S. Bhat

  DOI：10.1016/j.molcata.2014.05.017

  日期：2014.10

  para-Toluene sulphonic acid (p-TSA)-treated montmorillonite clay used as heterogeneous catalyst in acylation of para-cresol (PC) with aliphatic carboxylic acids. Reactions were studied under microwave and conventional modes of heating and reaction conditions were optimized by varying mole ratio, temperature, amount of catalyst and reaction time. Under optimized conditions the reaction was carried out involving p-cresol and decanoic acid. The reaction involved two steps, O-acylation involving ester formation followed by the Fries rearrangement involving C-acylation resulting in ketone product. Microwave heating mode showed higher conversion and the catalytic activity almost retained in repeated use. On the other hand the catalytic activity dropped by more than 50% in the case of conventional heating indicating rapid deactivation. A change in the color of the used catalyst was more intense in the case of conventional than in the microwave heating. Used catalysts were characterized for surface area and pore volume by BET technique, acidity by FTIR spectroscopy and amount of coke by TGA. Further investigations on the catalyst used in conventional heating revealed that the deactivation occurred during the O-acylation and not in the subsequent Fries rearrangement. However, the catalyst in the microwave irradiated reaction, exhibited a retarded rate of formation of coke precursors on the surface during O-acylation, thus preventing any decrease in catalytic activity. Present study indicates that the technique chosen for heating the reaction medium plays an important role in suppressing deactivation. (C) 2014 Elsevier B.V. All rights reserved.
• 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.