4-[2-(pyridin-2-yl)phenyl]butan-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4-[2-(pyridin-2-yl)phenyl]butan-2-one
• 英文别名: 4-(2-Pyridin-2-ylphenyl)butan-2-one
• 化学式: C₁₅H₁₅NO
• 分子量: 225.29
• InChiKey: RTJRKUTZVLXIHW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 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

• 作为反应物：
  描述：

  4-[2-(pyridin-2-yl)phenyl]butan-2-one 在 甲醇 、 sodium tetrahydroborate 作用下， 以97%的产率得到4-(2-(pyridin-2-yl)phenyl)butan-2-ol
  参考文献：
  名称：

  钌和铑催化的C–H键的氧化烷基化：有效地获得β-芳基酮†

  摘要：

  通用的定向芳族碳氢键与烯丙基醇之间已实现了钌和铑催化的氧化偶联。该方法以良好至优异的产率提供了功能性β-芳基酮和醛的有效合成，并且所需产物中的羰基是有机合成的重要合成子。

  DOI：

  10.1039/c3ob41590b
• 作为产物：
  描述：

  2-溴吡啶 在 四(三苯基膦)钯 、 bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] 、 sodium carbonate 、 双三氟甲烷磺酰亚胺银盐 作用下， 以 乙醇 、 水 、 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 24.0h， 生成 4-[2-(pyridin-2-yl)phenyl]butan-2-one
  参考文献：
  名称：

  Complete Switch of Selectivity in the C–H Alkenylation and Hydroarylation Catalyzed by Iridium: The Role of Directing Groups

  摘要：

  A complete switch in the Cp*Ir(III)-catalyzed paths between C-H olefination and hydroarylation was found to be crucially dependent on the type of directing groups. This dichotomy in product distribution was correlated to the efficiency in attaining syn-coplanarity of olefin-inserted 7-membered iridacycles. Theoretical studies support our hypothesis that the degree of flexibility of this key intermediate modulates the beta-H elimination, which ultimately affords the observed chemoselectivity.

  DOI：

  10.1021/jacs.5b09824

文献信息

• Rh(iii)-catalyzed dehydrogenative alkylation of (hetero)arenes with allylic alcohols, allowing aldol condensation to indenes
  作者：Zhuangzhi Shi、Mélissa Boultadakis-Arapinis、Frank Glorius

  DOI：10.1039/c3cc43903h

  日期：——

  Efficient Rh(III)-catalyzed C-H activation of different classes of (hetero)arenes such as 2-phenylpyridine, indoles, aryl ketones and acetanilide and their dehydrogenative cross-coupling with allylic alcohols are described. Several important skeletons such as beta-aryl aldehydes and ketones, 2-acetylindenes, 3,4-dihydro-1H-quinolin-2-one and quinoline could be produced using this protocol.

  描述了不同种类的（杂）芳烃如2-苯基吡啶，吲哚，芳基酮和对乙酰苯胺的Rh（III）催化的CH活化及其与烯丙醇的脱氢交叉偶联。使用此方案可以生产一些重要的骨架，例如β-芳基醛和酮，2-乙酰基茚，3,4-二氢-1H-喹啉-2-酮和喹啉。
• Carboxylate-Enhanced Rhodium(III)-Catalyzed Aryl C–H Alkylation with Conjugated Alkenes under Mild Conditions
  作者：Zhao Zhang、Mengyao Tang、Shengnan Han、Lutz Ackermann、Jie Li

  DOI：10.1021/acs.joc.6b02672

  日期：2017.1.6

  synthesis of β-aryl aldehydes and ketones from (hetero)aryl oximes, pyri(mi)dine, as well as pyrazoles and α,β-unsaturated carbonyl compounds has been developed under exceedingly mild reaction conditions. Thus, the versatile rhodium(III) catalysis features high step- and atom-economy, oxidant-free reaction conditions, and broad substrate scope.

  铑（III）催化的C–H键官能化可用于由（杂）芳基肟，吡啶（mi）dine以及吡唑和α，β-不饱和羰基化合物合成β-芳基醛和酮非常温和的反应条件。因此，通用的铑（III）催化具有高步阶和原子经济性，无氧化剂的反应条件以及广泛的底物范围。
• Mild Cobalt(III)-Catalyzed C-H Hydroarylation of Conjugated C=C/C=O Bonds
  作者：Jie Li、Zhao Zhang、Wenbo Ma、Mengyao Tang、Dawei Wang、Liang-Hua Zou

  DOI：10.1002/adsc.201700097

  日期：2017.5.17

  pyridyl, and pyrazolyl directing groups, thus overcoming the inherent C‐3 selectivity of an electrophilic indole derivatization. This approach provides an expedient route to indolyl‐substituted aldehydes, ketones, and esters with wide functional group tolerance. In addition, it also features high step‐ and atom‐economy.

  在温和的反应条件下，可实现高效的钴（III）催化的丙烯醛，烯酮和乙醛酸酯的C-2-选择性吲哚CHH氢芳基化反应。多功能的钴（III）催化剂在嘧啶基，吡啶基和吡唑基导向基团的辅助下表现出出色的位置选择性，从而克服了亲电吲哚衍生化固有的C-3选择性。这种方法为获得具有宽泛的官能团耐受性的吲哚基取代的醛，酮和酯提供了一条便捷的途径。此外，它还具有较高的阶跃和原子经济性。
• A manganese(<scp>i</scp>)tricarbonyl-catalyst for near room temperature alkene and alkyne hydroarylation
  作者：Shweta Choudhary、Diego M. Cannas、Matthew Wheatley、Igor Larrosa

  DOI：10.1039/d2sc04295a

  日期：——

  We have rationally designed a new Mn(I)-catalyst for hydroarylation reactions that displays much improved catalytic activity over the commonly used MnBr(CO)5. Our catalyst, MnBr(CO)3(MeCN)2, avoids the formation of the off-cycle manganacycle-(CO)4 species responsible for low catalyst activity, allowing near room temperature hydroarylation of alkenes and alkynes with broad functional group tolerance including

  使用丰富且低毒性的过渡金属开发更有效的催化工艺是使其在合成化学中得到主流应用的关键。我们合理地设计了一种用于加氢芳基化反应的新型 Mn( I ) 催化剂，其催化活性比常用的 MnBr(CO) 5显着提高。我们的催化剂 MnBr(CO) 3 (MeCN) 2避免了导致催化剂活性低的非循环锰环-(CO) 4物质的形成，允许在近室温下对烯烃和炔烃进行加氢芳基化，具有广泛的官能团耐受性，包括后期生物活性分子的阶段功能化和多样化。
• Regioselective alkylation of 2-phenylpyridines with terminal alkenes via C–H bond activation by a rhodium catalyst
  作者：Yeong-Gweon Lim、Jung-Bu Kang、Yong Hae Kim

  DOI：10.1039/p19960002201

  日期：——

  2-Phenylpyridine 1a reacts with various terminal alkenes in the presence of a rhodium(I) complex catalyst to give the corresponding mono ortho-alkylated products 2a-i and doubly alkylated products 3a-b (9:1), The same reaction using 3-methyl-2-phenylpyridine 1b gives the mono alkylated products 2j-n exclusively under the same reaction conditions due to steric hindrance between the methyl group of the pyridine and the alkyl group of 2j-n.