(E)-1-phenyl-3-(pyridin-2-yl)prop-2-en-1-one | 20890-12-4

• 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: (E)-1-phenyl-3-(pyridin-2-yl)prop-2-en-1-one
• 英文别名: 1-Phenyl-3-(pyridin-2-yl)prop-2-en-1-one；(E)-1-phenyl-3-pyridin-2-ylprop-2-en-1-one
• CAS: 20890-12-4
• 化学式: C₁₄H₁₁NO
• mdl: MFCD11936391
• 分子量: 209.247
• InChiKey: GYPWVWMVBAKTHW-MDZDMXLPSA-N

物化性质

• 熔点：
  53-54.5 °C
• 沸点：
  360.9±34.0 °C(Predicted)
• 密度：
  1.143±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  (E)-1-phenyl-3-(pyridin-2-yl)prop-2-en-1-one 在 sodium tetrahydroborate 、 1,10-菲罗啉 、 cerium(III) chloride heptahydrate 、 sodium t-butanolate 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 4.0h， 生成 1-苯基-3-(吡啶-2-基)丙烷-1-酮
  参考文献：
  名称：

  Transition-Metal-Free Self-Hydrogen-Transferring Allylic Isomerization

  摘要：

  Phenanthroline and tert-butoxide have been established as powerful radical initiators in reactions such as the S(RN)1-type coupling reactions due to the cooperation of large heteroarenes and a special feature of tert-butoxide. The first phenanthroline-tert-butoxide-catalyzed transition-metal-free allylic isomerization is described. The resulting ketones are key intermediates for indenes. The control experiments rule out the base-promoted allylic anion pathway. The radical pathway is supported by experimental evidence that includes kinetic study, kinetic isotope effect, isotope-labeling experiments, trapping experiments, and EPR experiments.

  DOI：

  10.1021/acs.orglett.5b03124
• 作为产物：
  描述：

  吡啶-2-甲醛 在 1,4-二氧六环 、 selenium(IV) oxide 、 水 、 sodium carbonate 作用下， 生成 (E)-1-phenyl-3-(pyridin-2-yl)prop-2-en-1-one
  参考文献：
  名称：

  Eistert; Munder, Chemische Berichte, 1958, vol. 91, p. 1415,1425

  摘要：

  DOI：

文献信息

• Copper-Mediated Cross-Dehydrogenative Coupling of 2-Methylpyridine and 8-Methylquinoline with Methyl Ketones and Benzamides
  作者：Gadde Sathish Kumar、Joshua William Boyle、Ciputra Tejo、Philip Wai Hong Chan

  DOI：10.1002/asia.201501096

  日期：2016.2

  synthetic method to prepare (E)‐(pyridin‐2‐yl)enones and (E)‐(quinolin‐8‐yl)enones that relies on the respective copper(I)‐catalyzed formal cross‐dehydrogenative coupling (CDC) reaction of 2‐methylpyridine and 8‐methylquinoline with methyl ketones has been discovered. The mechanism was delineated to follow a pathway involving oxidation of the N‐heterocycle to its corresponding aldehyde adduct prior

  合成方法（E）-（吡啶-2-基）烯酮和（E）-（喹啉-8-基）烯酮依赖于各自的铜（I）催化的正式交叉脱氢偶联（CDC）反应发现了2-甲基吡啶和8-甲基喹啉与甲基酮的混合物。机理被描述为遵循在与甲基酮反应之前将N-杂环氧化成其相应的醛加合物的途径。铜介导的CDC策略在反应性上的多功能性和与底物有关的差异以其在合成N-（喹啉-8-基甲基）酰胺和N中的应用为例-（喹啉-8-甲基）苯胺加成物，将交叉偶联伙伴转换为苯甲酰胺或苯胺衍生物。
• Iron-Facilitated Oxidative Radical Decarboxylative Cross-Coupling between α-Oxocarboxylic Acids and Acrylic Acids: An Approach to α,β-Unsaturated Carbonyls
  作者：Qing Jiang、Jing Jia、Bin Xu、An Zhao、Can-Cheng Guo

  DOI：10.1021/acs.joc.5b00267

  日期：2015.4.3

  The first Fe-facilitated decarboxylative cross-coupling reaction between α-oxocarboxylic acids and acrylic acids in aqueous solution has been developed. This transformation is characterized by its wide substrate scope and good functional group compatibility utilizing inexpensive and easily accessible reagents, thus providing an efficient and expeditious approach to an important class of α,β-unsaturated

  已经开发出水溶液中α-氧代羧酸与丙烯酸之间的第一个铁促进的脱羧交叉偶联反应。该转化的特征在于其底物范围宽和使用廉价且易于获得的试剂的良好官能团相容性，从而为生物活性化合物中常见的重要一类α，β-不饱和羰基化合物提供了一种有效而快捷的方法。在随后的官能化反应中也证明了偶联产物的合成潜力。初步的机理研究表明，该过程涉及自由基途径：
• [EN] A METHOD FOR PREPARING SULFUR-CONTAINING COMPOUNDS<br/>[FR] PROCÉDÉ POUR LA PRÉPARATION DE COMPOSÉS CONTENANT DU SOUFRE
  申请人：ROYAL COLLEGE OF SURGEONS IE

  公开号：WO2010066450A1

  公开（公告）日：2010-06-17

  The invention provides a method for preparing sulfur-containing compounds, the method comprising reacting a donor compound comprising at least one sulfur having at least one lone pair of electrons, with an acceptor compound; wherein the reaction occurs in the presence of an amine, optionally an amine catalyst, capable of activating the sulfur having at least one lone pair of electrons; and wherein the reaction occurs via the formation of an transient intermediate species, optionally a transient intermediate species, between the amine, optionally the amine catalyst and the donor compound; and wherein the donor compound is selected from the group consisting of a sulfurous acid, a sulfenic acid and a sulfinic acid or a salt, ester or amide of a sulfurous acid, a sulfenic acid and a sulfinic acid. The invention also provides sulfur-containing compounds of the formula: wherein R is selected from: (a) 1 -(4-Nitro-phenyl)-3-oxo-3-phenyl-propane; (b) 2-(3-Methyl-4-nitro-isoxazol-5-yl)-1 -phenyl-ethane; (c) 1-(4-Methoxy-phenyl)-2-(3-methyl-4-nitro-isoxazol-5-yl)-ethane; (d) 2-(3-Methyl-4-nitro-isoxazol-5-yl)-1-(4-nitro-phenyl)-ethane; (e) 1-(4-Fluoro-phenyl)-2-(3-methyl-4-nitro-isoxazol-5-yl)-ethane; (f) 1 -(4-Chloro-phenyl)-2-(3-methyl-4-nitro-isoxazol-5-yl)-ethane; and (g) 3-Oxo-cyclohexane. Finally, the invention provides use of chiral sulfur-containing compounds obtainable by the above-mentioned method or chiral sulfur-containing compounds as mentioned above for the resolution of racemic mixtures of amines.

  该发明提供了一种制备含硫化合物的方法，该方法包括将包含至少一个硫原子且至少一个孤对电子的给体化合物与受体化合物反应；其中，在胺的存在下进行反应，可选地，在能够激活至少一个硫原子具有至少一个孤对电子的胺的存在下进行反应；反应通过形成瞬态中间体物种进行，可选地，通过胺、可选地胺催化剂和给体化合物之间的瞬态中间体物种进行反应；给体化合物选自包括亚硫酸、亚硫酸和亚砜酸或亚硫酸、亚硫酸和亚砜酸的盐、酯或酰胺的群；该发明还提供了符合以下公式的含硫化合物：其中R选自：(a) 1-(4-硝基苯基)-3-氧代-3-苯基-丙烷；(b) 2-(3-甲基-4-硝基异噁唑-5-基)-1-苯基-乙烷；(c) 1-(4-甲氧基苯基)-2-(3-甲基-4-硝基异噁唑-5-基)-乙烷；(d) 2-(3-甲基-4-硝基异噁唑-5-基)-1-(4-硝基苯基)-乙烷；(e) 1-(4-氟苯基)-2-(3-甲基-4-硝基异噁唑-5-基)-乙烷；(f) 1-(4-氯苯基)-2-(3-甲基-4-硝基异噁唑-5-基)-乙烷；和(g) 3-氧代环己烷。最后，该发明提供了通过上述方法获得的手性含硫化合物或上述提到的手性含硫化合物用于分离胺的外消旋混合物。
• Methylene-Bridged Bis(imidazoline)-Derived 2-Oxopyrimidinium Salts as Catalysts for Asymmetric Michael Reactions
  作者：Andrey E. Sheshenev、Ekaterina V. Boltukhina、Andrew J. P. White、King Kuok Mimi Hii

  DOI：10.1002/anie.201300614

  日期：2013.7.1

  In nothing flat: The title salts, having planar nitrogen centers, were utilized successfully as phase‐transfer catalysts for asymmetric Michael reactions of tert‐butyl glycinate benzophenone Schiff base with vinyl ketone and chalcone derivatives, thus providing excellent levels of diastereo‐ and enantiocontrol (see scheme).

  一言以蔽之：具有平面氮中心的标题盐被成功地用作甘氨酸叔丁酯二苯甲酮席夫碱与乙烯基酮和查尔酮衍生物的不对称迈克尔反应的相转移催化剂，从而提供了极好的非对映和对映控制水平（见方案）。
• Novel Enantioselective Synthesis of Functionalized Pyridylarsanes by a Chiral Palladium Template Promoted Asymmetric Hydroarsanation Reaction
  作者：Fengli Liu、Sumod A. Pullarkat、Yongxin Li、Shuli Chen、Pak‐Hing Leung

  DOI：10.1002/ejic.200900460

  日期：2009.9

  hydroarsanation reaction with (E)-1-methyl-3-(pyridin-2-yl)-2-propenoate gave only one product as a six-membered As–N bidentate chelate. The naphthylamine auxiliary could be removed chemoselectively by treatment with concentrated hydrochloric acid to form the corresponding optically pure neutral complexes. Subsequent ligands displacement from the palladium using aqueous potassium cyanide generated the

  二苯基砷烷与 (E)-1-苯基-3-(吡啶-2-基)-2-丙烯酮和 (E)-1-甲基-3-(吡啶-2-基)-2-丙烯酸酯之间的不对称氢化砷化反应通过使用含有邻位金属化 (R)-[1-(二甲基氨基)乙基]萘的有机钯配合物作为手性反应模板，在温和条件下以高区域和立体选择性实现了这一目标。(E)-1-苯基-3-(吡啶-2-基)-2-丙烯酮与二苯基砷烷的氢化砷化生成两种立体异构产物，比例为3:1，作为手性萘胺钯上的五元As-N二齿螯合物模板。使用相同的手性金属模板，与 (E)-1-methyl-3-(pyridin-2-yl)-2-propenoate 的相应氢化砷化反应仅产生一种六元 As-N 双齿螯合物产物。萘胺助剂可以通过用浓盐酸处理化学选择性去除，形成相应的光学纯中性配合物。随后使用氰化钾水溶液从钯中置换配体产生光学纯的酮和酯官能化的手性吡啶基拉山配体。吡啶基拉烷的绝对构型和配位性质已通过单晶