2-bromo-4'-biphenylcarbonyl | 29267-44-5

• 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-bromo-4'-biphenylcarbonyl
• 英文别名: p-Phenylbenzoylbromid；4-PhC(=O)C6H4Br；[1,1'-Biphenyl]-4-carbonyl bromide；4-phenylbenzoyl bromide
• CAS: 29267-44-5
• 化学式: C₁₃H₉BrO
• 分子量: 261.118
• InChiKey: MBWXUJFBPLGAMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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-bromo-4'-biphenylcarbonyl 、 2-hex-3-ynyl-malonic acid dimethyl ester 在 tris-(dibenzylideneacetone)dipalladium(0) 、 dicyclohexyl(2',4',6'-triisopropyl-[1,1'-biphenyl]-3-yl)phosphine 、 sodium hexamethyldisilazane 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.33h， 以77%的产率得到dimethyl 3-(4-benzoylphenyl)-2-ethylcyclopent-2-ene-1,1-dicarboxylate
  参考文献：
  名称：

  Synthesis of 1,2-Disubstituted Cyclopentenes by Palladium-Catalyzed Reaction of Homopropargyl-Substituted Dicarbonyl Compounds with Organic Halides via 5-Endo-Dig Cyclization

  摘要：

  Palladium catalysts with bulky biaryl phosphine ligands allow homopropargyl-substituted dicarbonyl compounds to undergo intramolecular addition via a rare 5-endo-dig pathway. C-C bond forming reductive elimination follows the addition to Introduce alkenyl and alkynyl as well as aryl groups by using the corresponding organic halides. The cyclization is versatile enough to be applicable to the synthesis of highly substituted dihydropyrrole and a fused tricyclic compound.

  DOI：

  10.1021/ol301257m

文献信息

• Benzyl Derivatives of 2,1,3-Benzo- and Benzothieno[3,2-<i>a</i>]thiadiazine 2,2-Dioxides:  First Phosphodiesterase 7 Inhibitors
  作者：Ana Martínez、Ana Castro、Carmen Gil、Montserrat Miralpeix、Victor Segarra、Teresa Doménech、Jorge Beleta、Jose M. Palacios、Hamish Ryder、Xavier Miró、Carles Bonet、Josep M. Casacuberta、Ferran Azorín、Benjamí Piña、Pere Puigdoménech

  DOI：10.1021/jm990382n

  日期：2000.2.1

  The synthesis of a new family of benzyl derivatives of 2,1,3-benzo- and benzothieno[3,2-a]-thiadiazine 2,2-dioxides was achieved. The biological data revealed the first heterocyclic family of compounds with PDE 7 inhibitory properties appearing to be a new objective for the treatment of T-cell-dependent disorders. The IC50 values or percent inhibition values of the compounds against PDE 7 were calculated by testing them against human recombinant PDE 7 expressed in S, cerevisiae. In this expression system the only cyclic nucleotide hydrolyzing activity present in cell extracts corresponded to human PDE 7. Isoenzyme selectivity PDE 7 versus PDE 4 and PDE 3 was also measured. Considering simultaneously inhibition of the three different isoenzymes, monobenzyl derivatives 15 and 23 showed interesting PDE 7 potency (around 10 mu M); although not statistically significant, a trend toward selectivity with respect to PDE 3 and PDE 4 was obtained. Benzothiadiazine 16, although less potent at PDE 7 (IC50 25 mu M), also showed a trend of selectivity toward PDE 3 and PDE 4. These compounds are considered the best leads for further optimization.
• Synthesis of 1,2-Disubstituted Cyclopentenes by Palladium-Catalyzed Reaction of Homopropargyl-Substituted Dicarbonyl Compounds with Organic Halides via 5-<i>Endo-Dig</i> Cyclization
  作者：Daishi Fujino、Hideki Yorimitsu、Atsuhiro Osuka

  DOI：10.1021/ol301257m

  日期：2012.6.1

  Palladium catalysts with bulky biaryl phosphine ligands allow homopropargyl-substituted dicarbonyl compounds to undergo intramolecular addition via a rare 5-endo-dig pathway. C-C bond forming reductive elimination follows the addition to Introduce alkenyl and alkynyl as well as aryl groups by using the corresponding organic halides. The cyclization is versatile enough to be applicable to the synthesis of highly substituted dihydropyrrole and a fused tricyclic compound.