6,6-dimethoxy-4-tert-butyl-2,4-cyclohexadienone | 147088-66-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6,6-dimethoxy-4-tert-butyl-2,4-cyclohexadienone
• 英文别名: 4-Tert-butyl-6,6-dimethoxycyclohexa-2,4-dien-1-one
• CAS: 147088-66-2
• 化学式: C₁₂H₁₈O₃
• 分子量: 210.273
• InChiKey: SNCLNYSWFVQEBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6,6-dimethoxy-4-tert-butyl-2,4-cyclohexadienone 在 盐酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 0.03h， 以90%的产率得到4-tert-butyl-2-methyl-6-methoxyphenol
  参考文献：
  名称：

  Unanticipated participation of HCl in nucleophilic chlorination reaction: expedient route to meta chlorophenols

  摘要：

  o-Quinone monoketals participated in a 1,4-addition reaction with HCl furnishing m-chlorophenols in high yields. Several readily available o-quinone monoketals were selected to display the generality of this serendipitous and unprecedented reaction and the results are presented herein. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.11.012
• 作为产物：
  描述：

  甲醇 、 4-叔丁基-2-甲氧基苯酚 在 碘苯二乙酸 作用下， 以85%的产率得到6,6-dimethoxy-4-tert-butyl-2,4-cyclohexadienone
  参考文献：
  名称：

  通过涉及脱芳构化、区域选择性迈克尔加成反应和重芳构化的串联一锅法获得 3-芳基吲哚

  摘要：

  描述了在吲哚的 3 位引入氧化芳基的简便、通用和快速的方案。该方法由串联脱芳构化、区域选择性迈克尔加成反应和一锅三步序列中的重芳构化组成，以高产率获得 3-芳基吲哚。

  DOI：

  10.1002/ejoc.201400079

文献信息

• Oxidations of substituted phenols with hypervalent iodine : Applications to the phthalide annulation route to anthraquinones
  作者：Anthony S. Mitchell、Richard A. Russell

  DOI：10.1016/0040-4039(93)85123-e

  日期：1993.1

  Substituted phenols are oxidized by phenyliodonium diacetate in methanol to yield either cyclohexa-2,4- or the isomeric 2,5-dienones depending upon the structure of the phenol. Annulation of these oxidation products with the anion of 3-cyanophthalide affords access to a range of anthraquinones not previously accessible by this route.

  取代的苯酚在甲醇中被二乙酸苯基碘铵氧化，生成环己2,4-或异构体2,5-二烯酮，具体取决于苯酚的结构。这些氧化产物与3-氰基邻苯二甲酸酯的阴离子环合提供了以前通过该途径无法获得的一系列蒽醌。
• Oxidation with hypervalent iodine reagents. Part II: Novel cyclohexadienones as precursors for the synthesis of anthraquinones
  作者：Anthony S. Mitchell、Richard A. Russell

  DOI：10.1016/s0040-4020(97)00110-5

  日期：1997.3

  2,4-cyclohexadienones, 2,5-cyclohexadienones or mixtures of isomers, depending on the substrate being oxidized. Annulation of these cyclohexadienones with the anion of 3-cyanophthalide afforded anthraquinones in high yields.

  发现在甲醇中用二乙酸苯基碘铵取代的苯酚进行氧化可得到2,4-环己二酮，2,5-环己二酮或异构体的混合物，具体取决于被氧化的底物。这些环己二酮与3-氰基邻苯二甲酸酯的阴离子环化可高产率地得到蒽醌。
• Access to 3-Arylindoles through a Tandem One-Pot Protocol Involving Dearomatization, a Regioselective Michael Addition Reaction, and Rearomatization
  作者：Santhosh Kumar Chittimalla、Chennakesavulu Bandi、Sireesha Putturu、Rajesh Kuppusamy、Kevin Christopher Boellaard、David Chu Aan Tan、Demi Ming Jie Lum

  DOI：10.1002/ejoc.201400079

  日期：2014.4

  A facile, general and rapid protocol for the introduction of oxygenated aryls at the 3-position of indoles is described. This approach consists of a tandem dearomatization, a regioselective Michael addition reaction, and rearomatization in a one-pot three-step sequence to obtain 3-arylindoles in good yields.

  描述了在吲哚的 3 位引入氧化芳基的简便、通用和快速的方案。该方法由串联脱芳构化、区域选择性迈克尔加成反应和一锅三步序列中的重芳构化组成，以高产率获得 3-芳基吲哚。
• Reaction of Nitrile Oxides with Masked<i>o</i>-Benzoquinones; Synthesis of Highly Functionalized Isoxazolines
  作者：Santhosh Kumar Chittimalla、Rajesh Kuppusamy、Kamalraj Thiyagarajan、Chennakesavulu Bandi

  DOI：10.1002/ejoc.201201670

  日期：2013.5

  o-benzoquinones, on reaction with nitrile oxides generated in situ from the corresponding hydroxamoyl chlorides, provide [3+2] cycloaddition products or novel isoxazoline derivatives through an unprecedented rearrangement. The isolated [3+2] cycloadducts could be transformed into the corresponding isoxazoline derivatives in the presence of Et3N and highly functionalized benzisoxazoles in the presence

  掩蔽的邻苯醌与相应的异羟肟酰氯原位生成的腈氧化物反应，通过前所未有的重排提供 [3+2] 环加成产物或新型异恶唑啉衍生物。分离出的 [3+2] 环加合物在 Et3N 存在下可以转化为相应的异恶唑啉衍生物，在 4 N HCl 存在下可以转化为高度官能化的苯并异恶唑。
• A Detour Route for meta Functionalization of Phenols
  作者：Santhosh Chittimalla、Rajesh Kuppusamy、Chennakesavulu Bandi

  DOI：10.1055/s-0034-1378395

  日期：——

  Cyclohexadienones participate in a two-step procedure, a Michael addition followed by aromatization, providing hitherto difficult-to-synthesize meta-functionalized phenol derivatives in good yield. Application of the developed approach is exemplified by synthesizing C-aryl acetophenones, C-aryl glycines, and elemicin - an allylphenol natural product.