3'-hydroxymethyl-[1,1′]-biphenyl-2-carbaldehyde

• 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'-hydroxymethyl-[1,1′]-biphenyl-2-carbaldehyde
• 英文别名: 3'-(hydroxymethyl)biphenyl-2-carbaldehyde；3'-(Hydroxymethyl)-[1,1'-biphenyl]-2-carbaldehyde；2-[3-(hydroxymethyl)phenyl]benzaldehyde
• 化学式: C₁₄H₁₂O₂
• 分子量: 212.248
• InChiKey: SJWKDRUWRNQMNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  邻溴苯甲醛 、 3-羟甲基苯硼酸 在 1,1',1'',1'''-benzene-1,2,4,5-tetrayltetrakis(methylene)tetrakis-(piperidin-4-ol) 、 palladium diacetate 、 potassium carbonate 作用下， 以 乙醇 、 水 为溶剂， 以100%的产率得到3'-hydroxymethyl-[1,1′]-biphenyl-2-carbaldehyde
  参考文献：
  名称：

  作为铃木-宫浦交叉偶联反应配体的单分子 Tetrakis（piperdin-4-ol）的开发：Incrustoporin 和 Preclamol 的合成

  摘要：

  多米诺 aza-Cope/aza-Prins 级联反应合成了一类新的 4-羟基哌啶附加单分子、双、三和四单分子化合物，作为有效配体在有氧条件下催化 Suzuki-Miyaura 交叉偶联反应. 以良好到极好的收率获得了各种联芳基、三联苯和杂环联苯。配体还能够催化 Heck-Mizoroki 反应。作为应用，Suzuki-Miyaura 偶联反应用于合成肠壳孔蛋白、其类似物和药物分子 preclamol。

  DOI：

  10.1002/ejoc.201500353

文献信息

• 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.
• Development of Unimolecular Tetrakis(piperidin-4-ol) as a Ligand for Suzuki-Miyaura Cross-Coupling Reactions: Synthesis of Incrustoporin and Preclamol
  作者：Jothi L. Nallasivam、Rodney A. Fernandes

  DOI：10.1002/ejoc.201500353

  日期：2015.6

  cross-coupling reactions under aerobic conditions. Various biaryls, terphenyls, and heterocyclic biphenyls were obtained in good to excellent yields. The ligands were also capable of catalyzing the Heck–Mizoroki reaction. As an application, the Suzuki–Miyaura coupling reaction was used in the synthesis of incrustoporin, its analogs, and the drug molecule preclamol.

  多米诺 aza-Cope/aza-Prins 级联反应合成了一类新的 4-羟基哌啶附加单分子、双、三和四单分子化合物，作为有效配体在有氧条件下催化 Suzuki-Miyaura 交叉偶联反应. 以良好到极好的收率获得了各种联芳基、三联苯和杂环联苯。配体还能够催化 Heck-Mizoroki 反应。作为应用，Suzuki-Miyaura 偶联反应用于合成肠壳孔蛋白、其类似物和药物分子 preclamol。