(3r,5r,7r)-adamantan-1-yl(o-tolyl)methanone | 1193404-11-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3r,5r,7r)-adamantan-1-yl(o-tolyl)methanone
• 英文别名: 1-adamantyl-2-methylphenylmethanone；(1-Adamantyl)(2-methylphenyl)methanone；1-adamantyl-(2-methylphenyl)methanone
• CAS: 1193404-11-3
• 化学式: C₁₈H₂₂O
• mdl: MFCD18064517
• 分子量: 254.372
• InChiKey: XTNWPDZPDMBIRX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.611
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-金刚烷甲酸 在 4-二甲氨基吡啶 、 双(三环己基膦)二氯化钯 、 草酰氯 、 potassium carbonate 、 三乙胺 、 N,N-二甲基甲酰胺 、 三环己基膦 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 14.0h， 生成 (3r,5r,7r)-adamantan-1-yl(o-tolyl)methanone
  参考文献：
  名称：

  Acylative Suzuki coupling of amides: acyl-nitrogen activation via synergy of independently modifiable activating groups

  摘要：

  高效的Pd/PCy3催化的酰基化Suzuki偶联反应已经实现，可提供各种芳基酮，包括空间位阻大且难以接近的化合物。

  DOI：

  10.1039/c5cc00430f

文献信息

• Indium-mediated regioselective synthesis of ketones from arylstannanes under solvent-free ultrasound irradiation
  作者：Marcos J. Lo Fiego、Mercedes A. Badajoz、Claudia Domini、Alicia B. Chopa、María T. Lockhart

  DOI：10.1016/j.ultsonch.2012.10.018

  日期：2013.5

  drastically reduced (from 3-32h to 10-70min) under ultrasonic irradiation. Evidences for the involvement of a homolytic aromatic ipso-substitution mechanism, in which indium metal acts as radical initiator, are presented. It is possible the transference of two aryl groups from tin, thus improving effective mass yield, working with diarylstannanes as starting substrates.

  烷酰氯与空间和电子异构芳基锡的无溶剂铟促进反应是一种简单直接的方法，可以在温和的条件下良好地分离出高，极好的分离产率（42-84％）的伯，仲和叔烷基芳基酮和中立的条件。该方案对于合成芳基乙烯基酮也是足够的。在超声波照射下，反应时间大大减少（从3-32h减少到10-70min）。证据表明，其中均以铟金属为自由基引发剂的均质芳香族介孔取代机制参与其中。使用二芳基锡烷作为起始底物，可以从锡上转移两个芳基，从而提高有效的质量收率。
• Palladium-catalyzed acylative cross-coupling of amides with diarylborinic acids and sodium tetraarylborates
  作者：Xijing Li、Gang Zou

  DOI：10.1016/j.jorganchem.2015.07.009

  日期：2015.10

  A general and efficient acylative Suzuki coupling of active amides with diarylborinic acids has been achieved by using 1 mol% Pd(PCy3)(2)Cl-2/0.6 mol% PCy3 as catalyst system taking advantage of modifiable reactivities of acyl-nitrogen bonds of amides. Both electronic and steric influences from either aryl or acyl counterparts on the coupling proved to be negligible or small. A variety of aryl ketones including sterically hindered ones could be synthesized by the coupling of diarylborinic acids in good to excellent yields. Sodium tetraarylborates could also be used as high atom-economy aryl source in the palladium-catalyzed cross-coupling with active amides. (C) 2015 Elsevier B.V. All rights reserved.
• Catalyst-free alkanoylation of aromatic rings via arylstannanes. Scope and limitations
  作者：Marcos J. Lo Fiego、María T. Lockhart、Alicia B. Chopa

  DOI：10.1016/j.jorganchem.2009.07.019

  日期：2009.10

  The reaction of alkanoyl chlorides with arylstannanes in 1,2-dichlorobenzene (180 degrees C) is a simple and direct route for the catalyst-free and regioselective synthesis of tertiary alkyl aryl ketones in good to excellent isolated yields (55-77%). Nevertheless, under similar conditions, reactions carried out with alkanoyl chlorides bearing alpha-hydrogens render only the product of protodestannylation. (C) 2009 Elsevier B. V. All rights reserved.