2,6-dimethylfuchsone | 13135-13-2

• 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: 2,6-dimethylfuchsone
• 英文别名: 4-(Diphenylmethylidene)-2,6-dimethylcyclohexa-2,5-dien-1-one；4-benzhydrylidene-2,6-dimethylcyclohexa-2,5-dien-1-one
• CAS: 13135-13-2
• 化学式: C₂₁H₁₈O
• 分子量: 286.373
• InChiKey: AKCSOQPHQQYMOS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,6-dimethylfuchsone 在 三乙基硅烷 、 uranyl nirate hexahydrate 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以91%的产率得到4-benzhydryl-2,6-dimethylphenol
  参考文献：
  名称：

  Uranyl-catalyzed hydrosilylation of para-quinone methides: access to diarylmethane derivatives

  摘要：

  一种高效便捷的铀催化还原水硅烷基化反应被开发出来，其中采用硅烷作为还原剂，用于对对位醌亚甲基化合物进行反应。

  DOI：

  10.1039/d0ob02455d
• 作为产物：
  描述：

  2,6-二甲基苯酚 、 二氯二苯甲烷 反应 72.0h， 生成 2,6-dimethylfuchsone
  参考文献：
  名称：

  Koutek, Bohumir; Musil, Lubomir; Velek, Jiri, Collection of Czechoslovak Chemical Communications, 1981, vol. 46, # 10, p. 2540 - 2556

  摘要：

  DOI：

文献信息

• N-Heterocyclic carbene catalysed 1,6-hydrophosphonylation of p-quinone methides and fuchsones: an atom economical route to unsymmetrical diaryl- and triarylmethyl phosphonates
  作者：Panjab Arde、Ramasamy Vijaya Anand

  DOI：10.1039/c6ob00289g

  日期：——

  A convenient organocatalytic approach to access unsymmetrical diaryl- and triarylmethyl phosphonates using NHC as a Brønsted base catalyst is described. This atom-economical protocol enables the installation of phosphonate groups on p-quinone methides and fuchsones through a 1,6-conjugate addition of dialkylphosphites, and the corresponding phosphonates were obtained in excellent yields.

  描述了一种方便的有机催化方法，该方法使用NHC作为布朗斯台德碱催化剂来获得不对称的二芳基和三芳基甲基膦酸酯。通过这种原子经济的方案，可以通过亚磷酸二烷基酯的1，6-共轭加成将膦酸酯基团安装在对苯二甲酮和丁烯二酮上，并以极高的收率获得了相应的膦酸酯。
• B(C₆F₅)₃ catalysed reduction of para-quinone methides and fuchsones to access unsymmetrical diaryl- and triarylmethanes: elaboration to beclobrate
  作者：Sriram Mahesh、Ramasamy Vijaya Anand

  DOI：10.1039/c7ob02007d

  日期：——

  A mild and efficient method for the synthesis of unsymmetrical diaryl- and triarylmethanes through a B(C6F5)3 catalyzed reduction of para-quinone methides and fuchsones respectively, using the Hantzsch ester as a reducing source has been developed. Detailed mechanistic investigations revealed that the reaction actually proceeds through a Lewis acid–base pair complex derived from B(C6F5)3 and the Hantzsch

  已开发出一种温和有效的方法，该方法通过使用Hantzsch酯作为还原源，通过B（C 6 F 5）3分别催化对苯醌甲基化物和丁二酮的还原反应，合成不对称的二芳基甲烷和三芳基甲烷。详细的机械研究表明，该反应实际上是通过衍生自B（C 6 F 5）3和汉茨（Hantzsch）酯的路易斯酸-碱对络合物进行的。
• Accessing α-Arylated Nitriles via BF₃·OEt₂ Catalyzed Cyanation of <i>para</i>-Quinone Methides Using <i>tert-</i>Butyl Isocyanide as a Cyanide Source
  作者：Sachin R. Shirsath、Ganesh H. Shinde、Aslam C. Shaikh、M. Muthukrishnan

  DOI：10.1021/acs.joc.8b01926

  日期：2018.10.5

  for the synthesis of α-diaryl and α-triaryl nitriles has been reported. This protocol allows α-diaryl- and α-triaryl nitriles to be accessed in good to excellent yields and with a broad substrate scope, which could be further functionalized to give a versatile set of products. This is the first example wherein tert-butyl isocyanide has been used as a cyanide source for the 1,6-conjugate addition.

  已经报道了BF 3 ·OEt 2催化叔丁基异氰酸酯向对苯醌甲基化物和紫红色中的1，6-共轭加成反应，以合成α-二芳基和α-三芳基腈。该方案允许以良好的产率，优异的产率和广泛的底物范围使用α-二芳基和α-三芳基腈，可以进一步对其进行功能化，以提供一组通用的产品。这是第一个实例，其中叔丁基异氰化物已用作1，6-共轭加成的氰化物源。
• <i>N</i>-Heterocyclic Carbene Catalyzed 1,6-Conjugate Addition of Me₃Si-CN to <i>para</i>-Quinone Methides and Fuchsones: Access to α-Arylated Nitriles
  作者：Prithwish Goswami、Gurdeep Singh、Ramasamy Vijaya Anand

  DOI：10.1021/acs.orglett.7b00508

  日期：2017.4.21

  N-heterocyclic carbene (NHC) as a catalyst is described. This protocol comprises an NHC catalyzed activation of Me3Si-CN followed by 1,6-conjugate addition of cyanide to para-quinone methides (p-QMs) and fuchsones leading to α-diaryl- and α-triaryl nitriles in good to excellent yields.

  描述了使用N-杂环卡宾（NHC）作为催化剂的α-芳基腈的有机催化方法。该方案包括NHC催化的Me 3 Si-CN活化，然后将氰化物1,6-共轭加成到对苯醌甲基化物（p -QMs）和富马酮中，从而导致α-二芳基和α-三芳基腈的优劣。产量。
• Metal‐Free Aminocarbonylation of <i>p</i> ‐Quinone Methides with Isocyanides: Synthesis of Sterically Hindered α‐Arylated Acetamides
  作者：Sachin R. Shirsath、Devidas A. More、M. Muthukrishnan

  DOI：10.1002/asia.202200642

  日期：2022.10.17

  The synthesis of sterically hindered α-arylated acetamides generally requires a multistep reaction sequence and is also difficult to access due to steric constraints. This protocol allows the synthesis of sterically hindered α-arylated acetamides in moderate to high yields via 1,6-addition of isocyanides to p-quinone methides in the presence of BF3.OEt2.

  空间位阻α-芳基化乙酰胺的合成通常需要多步反应序列，并且由于空间限制也难以获得。该协议允许在存在 BF 3 .OEt 2的情况下，通过将异氰化物 1,6-加成到对醌甲基化物中，以中等至高产率合成空间位阻 α-芳基化乙酰胺。