2,4,6-trimethyl-6-methylthiomethylenecyclohexa-2,4-dien-1-one | 16184-96-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,4,6-trimethyl-6-methylthiomethylenecyclohexa-2,4-dien-1-one
• 英文别名: 6-methylthiomethyl-2,4,6-trimethyl-cyclohexadien-1-one；2,4,6-Trimethyl-6-thiomethoxymethyl-cyclohexa-2,4-dien-1-on；2,4,6-Trimethyl-6-(methylsulfanylmethyl)cyclohexa-2,4-dien-1-one
• CAS: 16184-96-6
• 化学式: C₁₁H₁₆OS
• 分子量: 196.313
• InChiKey: OYAIFWAPCYGKQP-UHFFFAOYSA-N

物化性质

• 沸点：
  298.8±9.0 °C(Predicted)
• 密度：
  1.004±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：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,4,6-trimethyl-6-methylthiomethylenecyclohexa-2,4-dien-1-one 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以79%的产率得到6-Methanesulfonylmethyl-2,4,6-trimethyl-cyclohexa-2,4-dienone
  参考文献：
  名称：

  Photocleavage coupling reactions between cyclohexa-2,4-dienone sulfone derivatives and amines by visible light irradiation

  摘要：

  A stable sulfone derivative of 2,4,6-trimethylcyclohexa-2,4-diene-1-one (7) undergoes facile ring cleavage under visible light to produce a ketene intermediate, which could be efficiently captured by amines to give amides even in the presence of competing nucleophiles such as water and ethanol. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00153-5
• 作为产物：
  描述：

  二甲基硫 、 2,4,6-三甲酚 在 N-氯代丁二酰亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 2,4,6-trimethyl-6-methylthiomethylenecyclohexa-2,4-dien-1-one
  参考文献：
  名称：

  Photocleavage coupling reactions between cyclohexa-2,4-dienone sulfone derivatives and amines by visible light irradiation

  摘要：

  A stable sulfone derivative of 2,4,6-trimethylcyclohexa-2,4-diene-1-one (7) undergoes facile ring cleavage under visible light to produce a ketene intermediate, which could be efficiently captured by amines to give amides even in the presence of competing nucleophiles such as water and ethanol. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00153-5

文献信息

• Reaction of phenols with t-butyl bromide–dimethyl sulphoxide. Methylthiomethylation versus bromination
  作者：Arnaldo Dossena、Rosangela Marchelli、Giuseppe Casnati

  DOI：10.1039/p19830001141

  日期：——

  t-Butyl bromide-activated dimethyl sulphoxide reacts with phenols to give either methylthiomethylation or bromination products. Several equilibria are shown to be simultaneously present in the system; however, by appropriate choice of several parameters (basicity, temperature, and reactant ratio) it is possible to drive the reaction selectively in one direction. A general discussion on the mechanism

  叔丁基溴化物活化的二甲基亚砜与酚反应生成甲硫基甲基化或溴化产物。系统中同时存在多个平衡点。然而，通过几个参数适当选择（碱度，温度，和反应物比），可以选择性地驱动所述反应在一个方向上。对这些反应的机理进行了一般性的讨论。
• 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。
• Sulfoxide-carbodiimide reactions. V. Reactions of 2,6-disubstituted phenols
  作者：Michael G. Burdon、John G. Moffatt

  DOI：10.1021/ja00994a028

  日期：1967.8
• Photochemically induced symmetrical coupling reactions between cyclohexa-2,4-dienones and α,ω-diamines. A new approach to the selective labelling of peptides and proteins
  作者：Derek H.R. Barton、Sung Kee Chung、Young Mee Kim、Tae Woo Kwon

  DOI：10.1016/s0960-894x(97)00096-6

  日期：1997.3

  2,4,6-Trimethylcyclohexa-2,4-dien-1-one derivatives undergo ring cleavage to furnish symmetrical amides on irradiation with visible light in the presence of various alpha,omega-diamines. Five different symmetrical amides containing a substituted diene moiety were synthesized in 65-85% yield. (C) 1997 Elsevier Science Ltd.
• Novel synthesis of cyclohexa-2,4-dien-1-ones. Its use in a partial synthesis of the chromophore portion of phomenoic acid
  作者：Ravindra Satish Topgi

  DOI：10.1021/jo00287a030

  日期：1989.12