3-(pyridin-3-yl)-1-(p-tolyl)propan-1-one | 1330172-83-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(pyridin-3-yl)-1-(p-tolyl)propan-1-one
• 英文别名: 3-(Pyridin-3-yl)-1-(p-tolyl)propan-1-one；1-(4-methylphenyl)-3-pyridin-3-ylpropan-1-one
• CAS: 1330172-83-2
• 化学式: C₁₅H₁₅NO
• 分子量: 225.29
• InChiKey: SBDQDHSNCVGYGG-UHFFFAOYSA-N

物化性质

• 熔点：
  59-62 °C
• 沸点：
  393.5±30.0 °C(Predicted)
• 密度：
  1.084±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-吡啶甲醇 、 1-(4-甲基苯基)-1-乙醇 在 C₃₈H₄₃IrN₂PS₂⁽¹⁺⁾*CF₃O₃S^(1-) 、 caesium carbonate 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以79%的产率得到3-(pyridin-3-yl)-1-(p-tolyl)propan-1-one
  参考文献：
  名称：

  Iridium–CNP complex catalyzed cross-coupling of primary alcohols and secondary alcohols by a borrowing hydrogen strategy

  摘要：

  通过伯醇和仲醇的交叉耦合，开发了一种高效形成碳-碳键的方法。利用铱-CNP配合物作为催化剂，通过借氢策略，获得了相应的功能化酮类化合物。目前的方法为aldol反应衍生物提供了一种简便的替代方法。更重要的是，这些配合物在芳香胺与叔�胺的烷基化反应中也是有效的催化剂。

  DOI：

  10.1039/c4ra06474g

文献信息

• Phosphine-Free NNN-Manganese Complex Catalyzed α-Alkylation of Ketones with Primary Alcohols and Friedländer Quinoline Synthesis
  作者：Milan K. Barman、Akash Jana、Biplab Maji

  DOI：10.1002/adsc.201800380

  日期：2018.9.3

  a very simple and inexpensive catalytic system based on Earth's abundant transition metal manganese and on a bench‐stable phosphine‐free NNN‐pincer ligand for an atom‐efficient α‐alkylations of ketones with primary alcohols via hydrogen‐autotransfer C−C bond formation protocol. The precatalyst could be generated in situ and could be activated by using catalytic amount of base under milder conditions

  在此，我们报告了一种非常简单且便宜的催化体系，该体系基于地球上大量的过渡金属锰和稳定的无膦NNN钳位配体，可通过氢自动转移C-与伯醇进行酮的原子高效α-烷基化C键形成协议。该预催化剂可以原位产生，并且可以通过在较温和的条件下使用催化量的碱来活化。酮类与多种伯醇可有效地多样化，分离收率良好至极佳。值得注意的是，该催化剂也可用于以2-氨基苄醇为烷基化剂的喹啉衍生物的合成。后面的反应是高度良性的，仅产生氢和水作为副产物。
• Direct α-alkylation of ketones with primary alcohols catalyzed by iridium–CNP complex
  作者：Dawei Wang、Keyan Zhao、Piming Ma、Chongying Xu、Yuqiang Ding

  DOI：10.1016/j.tetlet.2014.11.034

  日期：2014.12

  The α-alkylation of ketones with primary alcohols was realized by CC cross-coupling with iridium–CNP complexes as catalyst. This reaction proceeds via dehydrogenation reactions, aldol condensation, and hydrogenation using the borrowed hydrogen atoms from alcohols. The pyridyl methanols and other heterocyclic substituted methanols, especially alkyl alcohols, were also suitable for this transformation

  酮与伯醇的α-烷基化是通过铱-CNP络合物作为催化剂的C C交叉偶联实现的。该反应通过脱氢反应，醇醛缩合和使用从醇中借来的氢原子进行氢化而进行。吡啶基甲醇和其他杂环取代的甲醇，尤其是烷基醇，也适用于该转化。
• Rhodium-catalyzed alkylation of ketones and alcohols with alcohols
  作者：X. Yu、Q. Y. Wang、Q. J. Wu、D. W. Wang

  DOI：10.1134/s107036321601028x

  日期：2016.1

  alkylation of ketones and alcohols through the borrowing hydrogen strategy in the presence of rhodium complexes as catalyst was developed. This transformation is tolerant to various functional substrates and is efficient in C–C coupling of primary and secondary alcohols, which provides an alternative method of the synthesis of functional ketones from simple and commercially available materials.

  提出了在铑配合物作为催化剂存在下，通过借氢策略直接催化酮和醇烷基化的有效方法。这种转化可以耐受各种功能性底物，并且在伯醇和仲醇的C-C偶联中很有效，这为从简单的市售材料合成功能性酮提供了另一种方法。
• Efficient ruthenium-catalyzed α-alkylation of ketones using pyridyl methanols
  作者：Feng-Xia Yan、Min Zhang、Xiao-Ting Wang、Feng Xie、Meng-Meng Chen、Huanfeng Jiang

  DOI：10.1016/j.tet.2013.12.065

  日期：2014.2

  By employing an easily available [Ru(p-cymene)Cl-2](2)/Xantphos/t-BuOK catalyst system, the alpha-alkylation of ketones was demonstrated by using pyridyl methanol as the alkylating reagents. The synthetic protocol allows synthesizing a wide range of alpha-pyridyl methylated ketones in reasonable to excellent isolated yields with high atom-efficiency. The transformation is operationally simple, the substrate scope is wide, and the starting materials are readily-available. There is no need for addition of alkenes as the hydrogen receptors or the use of stoichiometric amount of base. (C) 2013 Elsevier Ltd. All rights reserved.
• Iridium–CNP complex catalyzed cross-coupling of primary alcohols and secondary alcohols by a borrowing hydrogen strategy
  作者：Dawei Wang、Keyan Zhao、Xin Yu、Hongyan Miao、Yuqiang Ding

  DOI：10.1039/c4ra06474g

  日期：——

  A highly efficient C–C bond formation has been developed through the cross-coupling of primary and secondary alcohols. The corresponding functionalized ketones were obtained with an iridium–CNP complex as a catalyst through the borrowing hydrogen strategy. The present methodology provides an easy alternative method to aldol reaction derivatives. More importantly, the complexes were also effective catalysts for the alkylation of an aromatic amine with a tertiary alkyl amine.

  通过伯醇和仲醇的交叉耦合，开发了一种高效形成碳-碳键的方法。利用铱-CNP配合物作为催化剂，通过借氢策略，获得了相应的功能化酮类化合物。目前的方法为aldol反应衍生物提供了一种简便的替代方法。更重要的是，这些配合物在芳香胺与叔�胺的烷基化反应中也是有效的催化剂。