4-(allyloxy)-2,4,6-trimethylcyclohexa-2,5-dien-1-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(allyloxy)-2,4,6-trimethylcyclohexa-2,5-dien-1-one
• 英文别名: 2,4,6-Trimethyl-4-prop-2-enoxycyclohexa-2,5-dien-1-one
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: BSBMWQGIJZVMBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  4-(allyloxy)-2,4,6-trimethylcyclohexa-2,5-dien-1-one 、 丙烯酸甲酯（MA） 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以65%的产率得到(E)-methyl 4-((1,3,5-trimethyl-4-oxocyclohexa-2,5-dien-1-yl)oxy)but-2-enoate
  参考文献：
  名称：

  Tandem Dienone Photorearrangement–Cycloaddition for the Rapid Generation of Molecular Complexity

  摘要：

  A tandem dienone photorearrangement-cycloaddition (DPC) reaction of novel cyclohexadienone substrates tethered with various 2 pi and 4 pi reaction partners resulted in the formation of polycyclic, bridged frameworks. In particular, use of alkynyl ether-tethered substrates led to (3 + 2) cycloaddition to afford strained alkenes which could be further elaborated by intra- and intermolecular cycloaddition chemistry to produce complex, polycyclic chemotypes.

  DOI：

  10.1021/ja409992m
• 作为产物：
  描述：

  (2,4,6-trimethylphenoxy)trimethylsilane 在 碘苯二乙酸 、 水 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 0.5h， 生成 4-(allyloxy)-2,4,6-trimethylcyclohexa-2,5-dien-1-one
  参考文献：
  名称：

  Tandem Dienone Photorearrangement–Cycloaddition for the Rapid Generation of Molecular Complexity

  摘要：

  A tandem dienone photorearrangement-cycloaddition (DPC) reaction of novel cyclohexadienone substrates tethered with various 2 pi and 4 pi reaction partners resulted in the formation of polycyclic, bridged frameworks. In particular, use of alkynyl ether-tethered substrates led to (3 + 2) cycloaddition to afford strained alkenes which could be further elaborated by intra- and intermolecular cycloaddition chemistry to produce complex, polycyclic chemotypes.

  DOI：

  10.1021/ja409992m

文献信息

• Rhodium(III)-catalyzed diastereo- and enantioselective hydrosilylation/cyclization reaction of cyclohexadienone-tethered α,β-unsaturated aldehydes
  作者：Yi-Fan Wang、Hao-Yun Yu、Hao Xu、Ya-Jie Wang、Xiaodi Yang、Yu-Hui Wang、Ping Tian、Guo-Qiang Lin

  DOI：10.1016/j.cclet.2024.109520

  日期：2024.1

  A rhodium(III)-catalyzed hydrosilylation/cyclization reaction of cyclohexadienone-tethered α,β-unsaturated aldehydes (1,6-dienes) with triethylsilane is described, providing a series of -hydrobenzofurans, -hydroindoles, and -hydroindenes bearing silyl enol ether in good to excellent yields and excellent stereoselectivities. Additionally, the versatility of this method was demonstrated through a gram-scale

  描述了铑(III)催化的环己二烯酮系链的α,β-不饱和醛(1,6-二烯)与三乙基硅烷的氢化硅烷化/环化反应，提供了一系列带有硅基烯醇醚的-氢苯并呋喃、-氢吲哚和-氢茚。具有良好至优异的产率和优异的立体选择性。此外，通过克级实验和各种下游转化证明了该方法的多功能性，突出了其实用性。
• Bromide-Assisted Oxidation of Substituted Phenols with Hydrogen Peroxide to the Correspondingp-Quinol andp-Quinol Ethers over WO42?-Exchanged Layered Double Hydroxides
  作者：B. F. Sels、D. E. De Vos、P. A. Jacobs

  DOI：10.1002/anie.200461555

  日期：2005.1
• Tandem Dienone Photorearrangement–Cycloaddition for the Rapid Generation of Molecular Complexity
  作者：Pieter H. Bos、Mitchell T. Antalek、John A. Porco、Corey R. J. Stephenson

  DOI：10.1021/ja409992m

  日期：2013.11.27

  A tandem dienone photorearrangement-cycloaddition (DPC) reaction of novel cyclohexadienone substrates tethered with various 2 pi and 4 pi reaction partners resulted in the formation of polycyclic, bridged frameworks. In particular, use of alkynyl ether-tethered substrates led to (3 + 2) cycloaddition to afford strained alkenes which could be further elaborated by intra- and intermolecular cycloaddition chemistry to produce complex, polycyclic chemotypes.