1-(but-3-enyl)pyridin-2(1H)-one | 1071155-39-9

• 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: 1-(but-3-enyl)pyridin-2(1H)-one
• 英文别名: 1-(But-3-en-1yl)pyridin-2(1h)-one；1-but-3-enylpyridin-2-one
• CAS: 1071155-39-9
• 化学式: C₉H₁₁NO
• 分子量: 149.192
• InChiKey: ISDIYKOBSKQEQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(but-3-enyl)pyridin-2(1H)-one 在 碘 作用下， 以 异丙醇 为溶剂， 反应 29.0h， 以61%的产率得到2-(iodomethyl)-3,4-dihydro-2H-pyrido[2,1-b][1,3]oxazinium triiodide
  参考文献：
  名称：

  Synthesis of 2-(halomethyl)-3,4-dihydro-2H-pyrido[2,1-b][1,3]oxazinium halides

  摘要：

  Alkylation of pyridin-2(1H)-one and 5-nitropyridin-2(1H)-one with 4-bromobut-1-ene afforded a mixture of N- and O-butenyl derivatives. 1-(But-3-en-1yl)pyridin-2(1H)-one and 1-(but-3-en-1-yl)-5-nitropyridin- 2(1H)-one reacted with bromine and iodine to give 2-(halomethyl)-3,4-dihydro-2H-pyrido[2,1-b][1,3]-oxazinium halides.

  DOI：

  10.1134/s1070428017070132
• 作为产物：
  描述：

  2-羟基吡啶 、 but-3-en-1-yl triflate 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.5h， 以91%的产率得到1-(but-3-enyl)pyridin-2(1H)-one
  参考文献：
  名称：

  通过简单的前体方法，通过将烯丙基镁酸锂添加到2-吡啶酮和RCM中，作为关键步骤，通过简单的前体方法合成官能化喹喔啉酮及其相关化合物的范围和局限性

  摘要：

  通过N H吡啶2（1 H）-酮（2-吡啶酮）的化学选择性N-烯基化，区域选择性加成烯丙基锂（二-正丁基）的化学合成N吡啶基简单地合成官能化的喹啉并丁4-酮的范围和局限性将镁酸盐（1-）转变为N-烯基吡啶-2（1 H）-，然后进行闭环复分解（RCM）。引入喹喔啉-4-酮环的许多功能化表明了支架合成中提出的策略的高前景。还介绍了它们扩展到吡啶并[1,2 - a ]氮杂环庚烷-4-酮和吡啶并[1,2 - a ]偶氮星-4-酮衍生物的合成以及螺环稠合化合物的合成。

  DOI：

  10.1016/j.tet.2014.09.043

文献信息

• Direct Alkenylation and Alkylation of Pyridone Derivatives by Ni/AlMe₃ Catalysis
  作者：Yoshiaki Nakao、Hiroaki Idei、Kyalo Stephen Kanyiva、Tamejiro Hiyama

  DOI：10.1021/ja907214t

  日期：2009.11.11

  derivatives are achieved through inter- and intramolecular insertion of alkynes, 1,3-dienes, and alkenes into the C(6)-H bond by nickel/AlMe(3) catalysis. Coordination of the heterocycles to the Lewis acid cocatalyst through their basic carbonyl oxygen is considered to be responsible for the regioselective activation of the C-H bonds, probably through oxidative addition to nickel(0).

  2-吡啶酮衍生物的区域选择性烯基化和烷基化是通过在镍/AlMe(3) 催化下将炔烃、1,3-二烯和烯烃插入 C(6)-H 键的分子间和分子内实现的。杂环通过它们的碱性羰基氧与路易斯酸助催化剂的配位被认为是导致 CH 键的区域选择性活化的原因，可能是通过氧化加成到镍 (0)。
• Regioselective Synthesis of 6-Vinyl-3,6-dihydropyridine-2(1<i>H</i>)-ones through Simple Addition of a Vinylmagnesium “Ate” Complex to 2-Pyridones
  作者：Jacek G. Sośnicki、Przemysław Dzitkowski、Łukasz Struk

  DOI：10.1002/ejoc.201500605

  日期：2015.8

  vinyldimethylmagnesate (vinylMe2MgLi), is obtained by mixing vinylmagnesium chloride (1 equiv.) and MeLi (in diethoxymethane; 2 equiv.). The application of this new reagent in the completely regioselective synthesis of 6-vinyl-3,6-dihydro-1H-pyridin-2(1H)-ones by simple 1,6-additions to 2-pyridones is described. Examination of the scope and limitations of the addition revealed the influence on the efficiency of the

  一种高度亲核的乙烯基化试剂，乙烯基二甲基镁酸锂（vinylMe2MgLi），是通过混合乙烯基氯化镁（1 当量）和 MeLi（在二乙氧基甲烷中；2 当量）获得的。描述了这种新试剂在 6-vinyl-3,6-dihydro-1H-pyridin-2(1H)-ones 的完全区域选择性合成中的应用，通过简单的 1,6-加成到 2-pyridones 进行了描述。对加成范围和限制的检查揭示了对氮原子和 2-吡啶酮环上的取代基的 6-乙烯基化反应效率的影响。
• Highly C3-Selective Direct Alkylation and Arylation of 2-Pyridones under Visible-Light-Promoted Photoredox Catalysis
  作者：Masahiro Miura、Koji Hirano、Atifah Najib、Sho Tabuchi

  DOI：10.3987/com-16-13459

  日期：——

  An Ir photoredox catalyst-mediated highly site-selective direct alkylation and arylation of 2-pyridones has been developed. Under visible-light-promoted conditions, ethyl 2-bromo-2,2-difluoroacetate couples with various 2-pyridones exclusively at the C3 position. A similar photoredox catalysis is also effective for the direct C3-arylation with diaryliodonium triflates. Thus, these reactions occurs under very mild conditions (blue LEDs irradiation and ambient temperature) to form the corresponding C3-alkylated and arylated 2-pyridones of potential interest in medicinal and pharmaceutical chemistry.
• Manganese-Mediated C3-Selective Direct Alkylation and Arylation of 2-Pyridones with Diethyl Malonates and Arylboronic Acids
  作者：Akihiro Nakatani、Koji Hirano、Tetsuya Satoh、Masahiro Miura

  DOI：10.1021/jo4027885

  日期：2014.2.7

  A manganese-mediated dehydrogenative direct alkylation of 2-pyridones with diethyl malonates has been developed. A similar reaction system is applicable to the direct arylation with arylboronic acids. These manganese-based reactions occur regioselectively at the C3 position of the 2-pyridones. The observed high C3 regioselectivity can complement precedented C-H functionalization protocols of the 2-pyridones in view of the site selectivity.
• Highly Active Nickel Catalysts for C–H Functionalization Identified through Analysis of Off-Cycle Intermediates
  作者：Alex J. Nett、Wanxiang Zhao、Paul M. Zimmerman、John Montgomery

  DOI：10.1021/jacs.5b04548

  日期：2015.6.24

  An inhibitory role of 1,5-cyclooctadiene (COD) in nickel-catalyzed,C-H functionalization processes as identified and studied. The bound COD participates in C-H activation by capturing the hydride, leading to a stable off-cycle pi-allyl complex that greatly diminished overall catalytic efficiency. Computational studies elucidated the origin of the effect and enabled identification of a 1,5-hexadiene-derived pre-catalyst that avoids the off-cycle intermediate and provides catalytic efficiencies that are superior to those of catalysts derived from Ni(COD)(2).