6-benzyl-2,6-dimethyl-cyclohexa-2,4-dienone | 31040-73-0

• 分子结构分类: 有机化合物
• 英文名称: 6-benzyl-2,6-dimethyl-cyclohexa-2,4-dienone
• 英文别名: 6-benzyl-2,6-dimethylcyclohexa-2,4-dien-1-one；6-Benzyl-2,6-dimethyl-cyclohexa-2,4-dienon；6-Benzyl-2.6-dimethylcyclohexa-2.4-dien-1-on
• CAS: 31040-73-0
• 化学式: C₁₅H₁₆O
• 分子量: 212.291
• InChiKey: IHMLXYLROSDKJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.32
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  6-benzyl-2,6-dimethyl-cyclohexa-2,4-dienone 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 20.0~22.0 ℃ 、30.0 kPa 条件下， 生成 6-benzyl-2,6-dimethylcyclohex-2-enone
  参考文献：
  名称：

  Stereoselective synthesis of cyclohexa-2,4-dien-1-ones and cyclohex-2-en-1-ones from phenols

  摘要：

  A convenient synthetic method for the synthesis of substituted cyclohex-2-en-1-ones by the direct alkylation of phenols has been developed. Furthermore, enantiomerically enriched 2,6-dimethyl-6-(3-methylbut-2-enyl)-cyclohexa-2,4-dienone was prepared by the deprotonation of 2,6-dimethylphenol with a sparteine-lithium complex followed by alkylation with 1-chloro-3-methylbut-2-ene. 2,6-Dimethyl-6-(3-methyl-but-2-enyl)-cyclohex-2-enone was prepared from the corresponding cyclohexa-2,4-dien-1-one by selective hydrogenation of the 4,5-double bond. The method was extended to 2-methyl-naphthalen-1-ol and 1-methyl-naphthalen-2-ol resulting in 2-(R)methyl-2-(3-methylbut-2-enyl)-2H-naphthalen- 1-one and 1-(S)-methyl-1-(3-methylbut-2-enyl)-1H-naphthalen-2-one, respectively. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.06.017
• 作为产物：
  描述：

  sodium 2,6-dimethylphenolate 、 溴甲苯 在 苯 作用下， 生成 6-benzyl-2,6-dimethyl-cyclohexa-2,4-dienone
  参考文献：
  名称：

  Factors Controlling Position of Alkylation of Alkali Metal Salts of Phenols, Benzyl and Allyl Halides^1,2

  摘要：

  DOI：

  10.1021/ja01539a030

文献信息

• Towards ortho-selective electrophilic substitution/addition to phenolates in anhydrous solvents
  作者：Eleana Lopušanskaja、Anni Kooli、Anne Paju、Ivar Järving、Margus Lopp

  DOI：10.1016/j.tet.2021.131935

  日期：2021.3

  solution lead to a mixture of o- and p-Bn-substituted phenols together with a substantial amount of phenol Bn ether. In CPME, and especially in toluene with 1–2 equivalents of ether or alcohol additives, ortho-selective alkylation is achieved. In the case of o,o,p-tri- and o,o-di-substituted phenols dearomatization occurs affording o-Bn-substituted alkyl cyclohexadienones with yields up to 92% with an o/p

  在水溶液中用BnBr进行烷基取代的Li-苯酚盐会生成邻和对Bn-取代的苯酚与大量的苯酚Bn醚的混合物。在CPME中，尤其是在具有1-2当量的醚或醇类添加剂的甲苯中，可以实现邻位选择性烷基化。在的情况下O，O-，P-三-和ö，ø -二-取代的苯酚脱芳构化，得到发生ø -Bn取代的烷基环己二烯酮与产率高达92％，其具有ø / p比高达90/1。
• Formation of Cyclohexadienones by Direct Alkylation of Phenols with Saturated Alkyl Derivatives¹
  作者：David Y. Curtin、Robert R. Fraser

  DOI：10.1021/ja01555a033

  日期：1958.11