3'-isopropyl-[1,1']-biphenyl-2-carbaldehyde | 916888-07-8

• 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: 3'-isopropyl-[1,1']-biphenyl-2-carbaldehyde
• 英文别名: 2-(3-Propan-2-ylphenyl)benzaldehyde
• CAS: 916888-07-8
• 化学式: C₁₆H₁₆O
• 分子量: 224.302
• InChiKey: KEGMCWIQIQHMOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  3'-isopropyl-[1,1']-biphenyl-2-carbaldehyde 在 zinc-copper couple 、 potassium carbonate 作用下， 以 甲醇 、 乙二醇二甲醚 、 乙醚 为溶剂， 生成
  参考文献：
  名称：

  联苯环丁烯酮光电环化

  摘要：

  在这项工作中，我们证明了容易获得的共轭双芳基环丁烯酮在暴露于 350 nm 光、TFA 和 TMSCl 时会发生光电环化反应以产生相应的二氢菲环丁酮。我们还发现环丁烯酮的电环化和环化反应处于平衡状态。

  DOI：

  10.1021/acs.joc.1c01809
• 作为产物：
  描述：

  2-溴苄醇 、 2-碘异丙基苯 在 降冰片烯 、 palladium diacetate 、 cesium pivalate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以95%的产率得到3'-isopropyl-[1,1']-biphenyl-2-carbaldehyde
  参考文献：
  名称：

  Formation of a carbonyl group ortho to a biaryl structure or a 6H-dibenzopyran by a palladium/norbornene-catalyzed ordered reaction sequence

  摘要：

  Developments are reported in the catalytic synthesis of biaryls containing an ortho-carbaldehyde or 6H-dibenzopyrans in the presence of palladium/norbornene as catalyst. The reaction of o-substituted aryl iodides and o-bromobenzyl alcohols proceeds by unsymmetrical aryl-aryl coupling to form a seven-membered oxapalladacycle intermediate, which may undergo an intramolecular redox process to form carbonyl groups or a C-O coupling to six-membered cyclic ethers. The predominant formation of di-benzopyrans as well as of biaryl structures containing the oxidized CHO group in one ring and the reduced CH2OH in the other is described along with some mechanistic insights. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.05.110

文献信息

• Unexpected Stereodynamic Consequences of the Restricted Rotations in <i>ortho</i>-Acyl- and <i>ortho</i>-Vinyl Biphenyls
  作者：Lodovico Lunazzi、Andrea Mazzanti、Mirko Minzoni

  DOI：10.1021/jo0613131

  日期：2006.12.1

  Surprisingly, the aryl−aryl rotation barriers of biphenyl derivatives ortho-substituted by the “small” HCO and HCCH2 groups (10.0 and 8.4 kcal mol-1, respectively) were found greater than those observed in biphenyls ortho-substituted by the “large” t-BuCO and t-BuCCH2 groups (6.7 and 6.9 kcal mol-1, respectively).

  出乎意料的是，发现被“小的” HC O和HC CH 2基团（分别为10.0和8.4 kcal mol -1）邻位取代的联苯衍生物的芳基-芳基旋转势垒比被OH邻位取代的联苯中观察到的更大。 “大” t -BuC O和t -BuC CH 2基团（分别为6.7和6.9 kcal mol -1）。
• A Sequential Pd/Norbornene-Catalyzed Process Generates <i>o-</i>Biaryl Carbaldehydes or Ketones via a Redox Reaction or 6<i>H</i>-Dibenzopyrans by C–O Ring Closure
  作者：Elena Motti、Nicola Della Ca’、Di Xu、Anna Piersimoni、Elena Bedogni、Zhi-Ming Zhou、Marta Catellani

  DOI：10.1021/ol302889t

  日期：2012.11.16

  o-Biaryl carbaldeydes and ketones are obtained through the one-pot reaction of o-aryl iodides with o-bromobenzyl alcohols under the catalytic action of Pd and norbornene, in the presence of a base. The same reaction can also give dibenzopyrans by Pd and norbornene catalysis with a different termination, leading to C-O ring closure. In both cases the process first leads to a five-membered palladacycle, which controls C-C coupling, then to a seven-membered oxapalladacycle, which gives aldehydes and ketones or dibenzopyrans.
• Formation of a carbonyl group ortho to a biaryl structure or a 6H-dibenzopyran by a palladium/norbornene-catalyzed ordered reaction sequence
  作者：Nicola Della Ca'、Marco Fontana、Di Xu、Mirko Cremaschi、Riccardo Lucentini、Zhi-Ming Zhou、Marta Catellani、Elena Motti

  DOI：10.1016/j.tet.2015.05.110

  日期：2015.9

  Developments are reported in the catalytic synthesis of biaryls containing an ortho-carbaldehyde or 6H-dibenzopyrans in the presence of palladium/norbornene as catalyst. The reaction of o-substituted aryl iodides and o-bromobenzyl alcohols proceeds by unsymmetrical aryl-aryl coupling to form a seven-membered oxapalladacycle intermediate, which may undergo an intramolecular redox process to form carbonyl groups or a C-O coupling to six-membered cyclic ethers. The predominant formation of di-benzopyrans as well as of biaryl structures containing the oxidized CHO group in one ring and the reduced CH2OH in the other is described along with some mechanistic insights. (C) 2015 Elsevier Ltd. All rights reserved.
• Biphenyl Cyclobutenone Photoelectrocyclizations
  作者：Changhang Dai、Xuchen Zhao、Changqing Song、Zach Schwartz、Jon D. Rainier

  DOI：10.1021/acs.joc.1c01809

  日期：2021.11.5

  In this work, we demonstrate that readily available conjugated bis-aryl cyclobutenones undergo photoelectrocyclization reactions to give the corresponding dihydrophenanthrene cyclobutanones when exposed to 350 nm light, TFA, and TMSCl. We have also found that cyclobutenone electrocyclizations and cycloreversions are in equilibrium.

  在这项工作中，我们证明了容易获得的共轭双芳基环丁烯酮在暴露于 350 nm 光、TFA 和 TMSCl 时会发生光电环化反应以产生相应的二氢菲环丁酮。我们还发现环丁烯酮的电环化和环化反应处于平衡状态。