2,6-dimethyl-2'-isopropylbiphenyl | 1482498-11-2

• 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-dimethyl-2'-isopropylbiphenyl
• 英文别名: 1,3-Dimethyl-2-(2-propan-2-ylphenyl)benzene；1,3-dimethyl-2-(2-propan-2-ylphenyl)benzene
• CAS: 1482498-11-2
• 化学式: C₁₇H₂₀
• 分子量: 224.346
• InChiKey: GBFJWMSIXXSPPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  2-氯-1,3-二甲苯 、 2-异丙基苯硼酸 在 potassium phosphate monohydrate 、 C₄₈H₄₅PRu 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以98%的产率得到2,6-dimethyl-2'-isopropylbiphenyl
  参考文献：
  名称：

  An Active, General, and Long-Lived Palladium Catalyst for Cross-Couplings of Deactivated (Hetero)aryl Chlorides and Bromides with Arylboronic Acids

  摘要：

  An active, general, and long-lived palladium catalyst for Suzuki-Miyaura reactions of aryl and heteroaryl chlorides deactivated by steric hindrance, electron richness, and coordinating functional groups is reported. In reactions of arylbromide bearing two o-tert-butyl substituents, C(sp(3))-H arylation of the tert-butyl group, rather than the Suzuki-Miyaura reaction, proceeded in excellent yield. The key to the success of the reactions was the development of biphenylene-substituted dicyclohexylruthenocenylphosphine (CyR-Phos) as a supporting ligand.

  DOI：

  10.1021/jo402089r

文献信息

• Univariate classification of phosphine ligation state and reactivity in cross-coupling catalysis
  作者：Samuel H. Newman-Stonebraker、Sleight R. Smith、Julia E. Borowski、Ellyn Peters、Tobias Gensch、Heather C. Johnson、Matthew S. Sigman、Abigail G. Doyle

  DOI：10.1126/science.abj4213

  日期：2021.10.15

  statistical analysis of reaction data with molecular descriptors to identify structure-reactivity relationships, which can enable prediction and mechanistic understanding. In this study, we developed a broadly applicable and quantitative classification workflow that identifies reactivity cliffs in 11 Ni- and Pd-catalyzed cross-coupling datasets using monodentate phosphine ligands. A distinctive ligand steric

  化学家经常使用具有分子描述符的反应数据的统计分析来识别结构-反应性关系，这可以实现预测和机理理解。在这项研究中，我们开发了一个广泛适用的定量分类工作流程，该工作流程使用单齿膦配体识别 11 个 Ni 和 Pd 催化的交叉偶联数据集中的反应性悬崖。发现一个独特的配体空间描述符，最小百分比埋藏体积 [% V bur (min)] 将这些数据集划分为具有相似阈值的活动和非活动区域。有机金属研究表明，该阈值对应于双配金属与单配金属的二元结果，以及 % V bur(min) 是催化中配体结构的物理意义和预测表示。
• An Active, General, and Long-Lived Palladium Catalyst for Cross-Couplings of Deactivated (Hetero)aryl Chlorides and Bromides with Arylboronic Acids
  作者：Takashi Hoshi、Tomonobu Honma、Ayako Mori、Maki Konishi、Tsutomu Sato、Hisahiro Hagiwara、Toshio Suzuki

  DOI：10.1021/jo402089r

  日期：2013.11.15

  An active, general, and long-lived palladium catalyst for Suzuki-Miyaura reactions of aryl and heteroaryl chlorides deactivated by steric hindrance, electron richness, and coordinating functional groups is reported. In reactions of arylbromide bearing two o-tert-butyl substituents, C(sp(3))-H arylation of the tert-butyl group, rather than the Suzuki-Miyaura reaction, proceeded in excellent yield. The key to the success of the reactions was the development of biphenylene-substituted dicyclohexylruthenocenylphosphine (CyR-Phos) as a supporting ligand.