2-allyl-6-(1-methylpropyl)phenol | 74926-88-8

• 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-allyl-6-(1-methylpropyl)phenol
• 英文别名: 2-allyl-6-sec-butylphenol；2-Allyl-6-sec-butyl-phenol；2-Butan-2-yl-6-prop-2-enylphenol
• CAS: 74926-88-8
• 化学式: C₁₃H₁₈O
• 分子量: 190.285
• InChiKey: AHGHRZIARCKVRL-UHFFFAOYSA-N

物化性质

• 沸点：
  98-102 °C(Press: 2 Torr)
• 密度：
  0.956±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  14
• 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：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-allyl-6-(1-methylpropyl)phenol 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 25.0 ℃ 、101.32 kPa 条件下， 反应 0.25h， 以66%的产率得到2-丁烷-2-基-6-丙基苯酚
  参考文献：
  名称：

  Synthesis, biological evaluation, and preliminary structure-activity considerations of a series of alkylphenols as intravenous anesthetic agents

  摘要：

  Following our discovery of the intravenous (iv) anesthetic activity of 2,6-diethylphenol in mice, a series of alkylphenols was examined in this species and the most active analogues were further evaluated in rabbits. The synthesis of compounds which were not commercially available was accomplished by adaptations of standard ortho-alkylation procedures for phenols. Structure-activity relationships were found to be complex, but, in general, potency and kinetics appeared to be a function of both the lipophilic character and the degree of steric hindrance exerted by ortho substituents. The most interesting compounds were found in the 2,6-dialkyl series, and the greatest potency was associated with 2,6-di-sec-alkyl substitution. In particular, 2,6-diisopropylphenol (ICI 35 868) emerged as a candidate for further development and has subsequently been shown to be an effective iv anesthetic agent in man.

  DOI：

  10.1021/jm00186a013
• 作为产物：
  描述：

  2-仲丁基苯酚 在 sodium hydroxide 、 苄基三丁基溴化铵 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 生成 2-allyl-6-(1-methylpropyl)phenol
  参考文献：
  名称：

  Synthesis, biological evaluation, and preliminary structure-activity considerations of a series of alkylphenols as intravenous anesthetic agents

  摘要：

  Following our discovery of the intravenous (iv) anesthetic activity of 2,6-diethylphenol in mice, a series of alkylphenols was examined in this species and the most active analogues were further evaluated in rabbits. The synthesis of compounds which were not commercially available was accomplished by adaptations of standard ortho-alkylation procedures for phenols. Structure-activity relationships were found to be complex, but, in general, potency and kinetics appeared to be a function of both the lipophilic character and the degree of steric hindrance exerted by ortho substituents. The most interesting compounds were found in the 2,6-dialkyl series, and the greatest potency was associated with 2,6-di-sec-alkyl substitution. In particular, 2,6-diisopropylphenol (ICI 35 868) emerged as a candidate for further development and has subsequently been shown to be an effective iv anesthetic agent in man.

  DOI：

  10.1021/jm00186a013

文献信息

• Convenient Synthesis of 2,4-Cyclohexadien-1-ones by Regioselective Methylthiomethylation of Phenols.
  作者：Sadamu KATAYAMA、Toshio WATANABE、Masashige YAMAUCHI

  DOI：10.1248/cpb.41.439

  日期：——

  A convenient synthesis of a variety of 2, 4-cyclohexadien-1-ones 3-7 is described. Reaction of various phenols 2 having appropriate substituents with an excess of S, S-dimethylsuccinmidosulfonium chloride (Corey-Kim reagent, 1)in the presence of triethylamine proceeded with regioselective methylthiomethylation to give methylthiomethyl, bis(methylthiomethyl), or tris(methylthiomethyl)-2, 4-cyclohexadien-1-ones 3-7 in satisfactory yields.

  描述了一种便捷合成多种2,4-环己二烯-1-酮（3-7）的方法。将具有适当取代基的各种酚（2）与过量的S,S-二甲基琥珀酰亚胺磺酸盐氯化物（Corey-Kim Reagent，1）在存在三乙胺的条件下反应，经过区域选择性甲硫基甲基化，得到甲硫基甲基、双（甲硫基甲基）或三（甲硫基甲基）-2,4-环己二烯-1-酮（3-7），产率令人满意。
• Organocatalytic enantioselective Friedel–Crafts alkylation of simple phenols with trifluoropyruvate
  作者：Jun-Ling Zhao、Li Liu、Chun-Ling Gu、Dong Wang、Yong-Jun Chen

  DOI：10.1016/j.tetlet.2007.12.129

  日期：2008.2

  Enantioselective Friedel–Crafts alkylation of simple phenols (4a–j) with 3,3,3-trifluoropyruvate (3) was accomplished by using chiral cinchona alkaloid catalyst 2h (10 mol %). High yields and enantioselectivities (71–94% ee) of the Friedel–Crafts alkylation products were obtained.

  通过使用手性金鸡纳生物碱催化剂2h（10 mol％），将简单的酚（4a – j）与3,3,3-三氟丙酮酸（3）进行对映选择性Friedel–Crafts烷基化。获得了Friedel-Crafts烷基化产品的高收率和对映选择性（71-94％ee）。
• 2-allyl-6-secondarybutylphenyl ester of benzoic acid
  申请人：DOW CHEMICAL CO

  公开号：US02500901A1

  公开（公告）日：1950-03-14
• Synthesis, biological evaluation, and preliminary structure-activity considerations of a series of alkylphenols as intravenous anesthetic agents
  作者：Roger James、John B. Glen

  DOI：10.1021/jm00186a013

  日期：1980.12

  Following our discovery of the intravenous (iv) anesthetic activity of 2,6-diethylphenol in mice, a series of alkylphenols was examined in this species and the most active analogues were further evaluated in rabbits. The synthesis of compounds which were not commercially available was accomplished by adaptations of standard ortho-alkylation procedures for phenols. Structure-activity relationships were found to be complex, but, in general, potency and kinetics appeared to be a function of both the lipophilic character and the degree of steric hindrance exerted by ortho substituents. The most interesting compounds were found in the 2,6-dialkyl series, and the greatest potency was associated with 2,6-di-sec-alkyl substitution. In particular, 2,6-diisopropylphenol (ICI 35 868) emerged as a candidate for further development and has subsequently been shown to be an effective iv anesthetic agent in man.