2,6-di(4-methylphenyl)benzaldehyde | 1174744-75-2

• 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-di(4-methylphenyl)benzaldehyde
• 英文别名: 4,4''-dimethyl-[1,1':3',1''-terphenyl]-2'-carbaldehyde；2,6-di(4'-tolyl)benzaldehyde；2,6-Bis(4-methylphenyl)benzaldehyde；2,6-bis(4-methylphenyl)benzaldehyde
• CAS: 1174744-75-2
• 化学式: C₂₁H₁₈O
• 分子量: 286.373
• InChiKey: BQNOZSRRWOQCRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  22
• 可旋转键数：
  3
• 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-di(4-methylphenyl)benzaldehyde 在 tetrakis(acetonitrile)palladium(II) tetrafluoroborate 、 三氟化硼乙醚 作用下， 以 四氢呋喃 为溶剂， 反应 3.08h， 生成 9-fluoro-7-methyl-1-(4-methylphenyl)phenanthrene
  参考文献：
  名称：

  Pinpoint-fluorinated phenanthrene synthesis based on CF bond activation of difluoroalkenes

  摘要：

  Treatment with a cationic palladium(II) catalyst promoted the Friedel-Crafts-type cyclization of 1,1-difluoro-1-alkenes bearing a biphenyl skeleton to afford regioselectively fluorinated (pinpoint-fluorinated) phenanthrenes via C-F bond activation. The obtained pinpoint-fluorinated phenanthrenes were observed to be organized by pi-pi and C-H center dot center dot center dot F interactions to exhibit columnar and layer structures in the solid state. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2015.06.008
• 作为产物：
  描述：

  2,6-二羟基苯甲醛 在 四(三苯基膦)钯 、 三氟甲磺酸酐 、 sodium carbonate 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 、 水 为溶剂， 反应 9.5h， 生成 2,6-di(4-methylphenyl)benzaldehyde
  参考文献：
  名称：

  Pinpoint-fluorinated phenanthrene synthesis based on CF bond activation of difluoroalkenes

  摘要：

  Treatment with a cationic palladium(II) catalyst promoted the Friedel-Crafts-type cyclization of 1,1-difluoro-1-alkenes bearing a biphenyl skeleton to afford regioselectively fluorinated (pinpoint-fluorinated) phenanthrenes via C-F bond activation. The obtained pinpoint-fluorinated phenanthrenes were observed to be organized by pi-pi and C-H center dot center dot center dot F interactions to exhibit columnar and layer structures in the solid state. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2015.06.008

文献信息

• Selective Alkylation and Arylation of C–F Bond with Grignard Reagents
  作者：Faguan Lu、Hongjian Sun、Aiqin Du、Lei Feng、Xiaoyan Li

  DOI：10.1021/ol403479r

  日期：2014.2.7

  polyfluoroaryl imines with Grignard reagents were discovered in the absence of metal catalysts. The aldazine-N atom as an anchoring group has a special effect on the regioselectivity of the reaction. The C═N bond addition reaction with Grignard reagents was also explored. A possible mechanism was proposed on the competition between the nucleophilic substitution and addition reaction.

  在没有金属催化剂的情况下，发现了用格氏试剂对多氟芳基亚胺的CF键进行选择性烷基化和芳基化。作为锚定基团的恶嗪-N原子对反应的区域选择性具有特殊的影响。还研究了与格氏试剂的C═N键加成反应。提出了亲核取代与加成反应竞争的可能机制。
• Formation of Five- and Seven-Membered Rings Enabled by the Triisopropylsilyl Auxiliary Group
  作者：Dmitry L. Usanov、Hisashi Yamamoto

  DOI：10.1021/ol203209b

  日期：2012.1.6

  to 2-indanones from aldehydes was established. The introduction of a triisopropylsilyl group greatly facilitated Meinwald rearrangement of the intermediate epoxides and alleviated the necessity of polysubstitution for the clean formation of indenes and cyclopentadienes via cyclodehydration of allylic alcohols; unprecedented freedom with respect to the product structure was thus achieved. The developed

  建立了从醛到2-茚满酮的高度方便的合成途径。三异丙基甲硅烷基的引入极大地促进了中间环氧化物的迈因瓦尔德重排，并减轻了通过烯丙基醇的环化脱水干净形成茚满和环戊二烯的多取代的必要性。这样就实现了产品结构方面前所未有的自由。所开发的方法也可以适用于形成二元环[7]环和二苯并亚砜的七元环的形成。
• Chromium-catalyzed couplings of C(aryl)–SMe bonds for accessing arylated and alkylated benzaldehyde derivatives
  作者：Haohao Zeng、Shangru Yang、Chao Li、Fei Fan、Liang Ling、Meiming Luo、Xiaoming Zeng

  DOI：10.1039/d2cc01631a

  日期：——

  functionalized benzaldehydes under mild conditions. This reaction was promoted specifically by a low-cost and simple CrCl2 salt used as a precatalyst, enabling synchronous activations of ortho-C(aryl)–SMe and ortho′-C(aryl)–H bonds to achieve difunctionalization of benzaldimines. This work provided a strategy for accessing arylated, alkylated, and diarylated benzaldehyde derivatives as a result of

  这里描述的是铬催化的 C(芳基)-SMe 键断裂，导致在温和条件下与有机镁偶联得到官能化苯甲醛。该反应通过一种用作预催化剂的低成本且简单的 CrCl 2盐来特别促进，使邻-C(芳基)-SMe 和邻'-C(芳基)-H 键同步活化以实现苯扎亚胺的双官能化。由于 C(芳基)-SMe 和 C(芳基)-SMe/C(芳基)-H 键的偶联在具有成本效益的 Cr 催化作用下得到促进，这项工作提供了一种获取芳基化、烷基化和二芳基化苯甲醛衍生物的策略.
• Palladium-catalyzed site-selective arylation of symmetric dichlorobenzaldehyde to non-symmetric diaryl benzaldehyde via Suzuki coupling
  作者：Raju Dey、Brindaban C. Ranu

  DOI：10.1016/j.tetlet.2012.01.014

  日期：2012.3

  Arylation of 2,6-dichlorobenzaldehyde by aryl boronic acids via site-selective Suzuki coupling catalyzed by PdCl2 supported on 4 A molecular sieves produces 2-aryl-6-chlorobenzaldehyde which on subsequent coupling with a different aryl boronic acid in the presence of Pd(OAc)(2)-NHC ligand leads to non-symmetric diaryl benzaldehyde in good overall yield. (C) 2012 Elsevier Ltd. All rights reserved.
• Pinpoint-fluorinated phenanthrene synthesis based on CF bond activation of difluoroalkenes
  作者：Kohei Fuchibe、Toshiyuki Morikawa、Ryu Ueda、Tatsuo Okauchi、Junji Ichikawa

  DOI：10.1016/j.jfluchem.2015.06.008

  日期：2015.11

  Treatment with a cationic palladium(II) catalyst promoted the Friedel-Crafts-type cyclization of 1,1-difluoro-1-alkenes bearing a biphenyl skeleton to afford regioselectively fluorinated (pinpoint-fluorinated) phenanthrenes via C-F bond activation. The obtained pinpoint-fluorinated phenanthrenes were observed to be organized by pi-pi and C-H center dot center dot center dot F interactions to exhibit columnar and layer structures in the solid state. (C) 2015 Elsevier B.V. All rights reserved.