1-(4-methoxyphenyl)hex-2-yn-1-one | 108462-77-7

• 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: 1-(4-methoxyphenyl)hex-2-yn-1-one
• CAS: 108462-77-7
• 化学式: C₁₃H₁₄O₂
• 分子量: 202.253
• InChiKey: WOCWYTOFKYDQHA-UHFFFAOYSA-N

物化性质

• 沸点：
  326.7±44.0 °C(Predicted)
• 密度：
  1.040±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-methoxyphenyl)hex-2-yn-1-one 在 三苯基膦 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 反应 6.0h， 以40%的产率得到2-乙基-5-(4-甲氧基苯基)呋喃
  参考文献：
  名称：

  新型钯催化的炔酮向呋喃的重排

  摘要：

  在Pd（dba）2 -PPh 3催化剂存在下1-芳基-4-烷基-2-丁炔-1-酮的新型重排以适中的收率得到了2,4-取代的呋喃。

  DOI：

  10.1016/s0040-4039(00)85090-x
• 作为产物：
  描述：

  1-戊炔 、 对甲氧基苯甲酰氯 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 1-(4-methoxyphenyl)hex-2-yn-1-one
  参考文献：
  名称：

  Novel Microwave-Assisted One-Pot Synthesis of Isoxazoles by a Three-Component Coupling-Cycloaddition Sequence

  摘要：

  在介电加热条件下，通过羟胺酰氯现场生成的腈氧化物与末端炔烃进行连续的Sonogashira偶联，随后进行1,3-偶极环加成反应，以中等到良好的产率制备了异恶唑，实现了一种一锅法三组分反应。

  DOI：

  10.1055/s-2007-1000856

文献信息

• PPh₃-KOBu^t–Mediated Cyclization Reaction of <font>β</font>-Ketoesters with Alkynyl Ketones: Synthesis of Functionalized 2-Pyrones
  作者：Bin Hu、Ling-Guo Meng、Xiao-Li Hao、Mao Liang、Song Xue

  DOI：10.1080/00397911.2010.517374

  日期：2011.11.1

  Abstract Cyclization of alkynyl ketones with β-ketoesters mediated by PPh3 and KOBut to synthesize 2-pyrone derivatives was systematically described. A variety of β-ketoesters reacted with alkynyl ketones to give functionalized 2-pyrones in moderate to good yields under mild conditions.

  摘要 系统地描述了由 PPh3 和 KOBut 介导的炔基酮与 β-酮酯环化合成 2-吡喃酮衍生物。各种 β-酮酯与炔基酮反应，在温和条件下以中等至良好的产率得到官能化的 2-吡喃酮。
• Synthesis of Ynones via Recyclable Polystyrene-Supported Palladium(0) Complex Catalyzed Acylation of Terminal Alkynes with Acyl Chlorides under Copper- and Solvent-Free Conditions
  作者：Mohammad Bakherad、Ali Keivanloo、Bahram Bahramian、Saeideh Jajarmi

  DOI：10.1055/s-0030-1259322

  日期：2011.2

  Herein, a highly efficient method for the copper- and solvent-freecoupling reaction of acyl chlorides and terminal alkynes catalyzedby 1-phenyl-1,2-propanedione-2-oxime thiosemicarbazone-functionalizedpolystyrene resin-supported Pd(0) complex is described. Acyl chloridesare easily coupled with terminal alkynes, giving good to high yieldsin the presence of a low catalyst loading (1 mol% Pd) inEt 3 N

  在此，描述了一种由 1-苯基-1,2-丙二酮-2-肟氨基硫脲官能化聚苯乙烯树脂负载的 Pd(0) 配合物催化的酰氯和末端炔烃的无铜和无溶剂偶联反应的高效方法。酰氯很容易与末端炔烃偶联，在室温和有氧条件下，在 Et 3 N 中存在低催化剂负载量（1 mol% Pd）的情况下，可产生良好或高产率。离心后，负载型催化剂可以回收和重复使用多次，活性仅略有下降。
• Carbonylative Sonogashira Coupling of Aryl Iodides with Terminal Alkynes Catalyzed by Palladium Nanoparticles
  作者：Xiujuan Feng、Jiliang Song、Ming Bao

  DOI：10.1002/jccs.201700302

  日期：2018.3

  synthesis of α,β‐alkynyl ketones from the three‐component coupling of aryl iodides, terminal alkynes, and carbon monoxide (carbonylative Sonogashira coupling reaction) is successfully developed. The carbonylative Sonogashira coupling reaction proceeded smoothly under mild conditions in the presence of palladium nanoparticles to produce the corresponding α,β‐alkynyl ketones in good to excellent yields.

  成功开发了一种由芳基碘化物，末端炔烃和一氧化碳的三组分偶合（羰基Sonogashira偶合反应）合成α，β-炔基酮的简便有效的方法。羰基Sonogashira偶联反应在钯纳米粒子存在的条件下在温和条件下平稳进行，可产生相应的α，β-炔基酮，收率良好。
• Michael Addition-Lactonization Reaction of Electron-Deficient Alkynes with N-(Diphenylmethylene)glycinates: An Efficient Synthesis of 3-Amino-2-pyrone Derivatives
  作者：Tao Lu、Qing-Fa Zhou、Yong Zhu、Wei-Fang Tang

  DOI：10.1055/s-0029-1217098

  日期：2010.1

  approach is based on the Michael addition of N-(diphenylmethylene)glycinates to various alkynyl ketones, followed by lactonization using 10 mol% sodium hydroxide as catalyst. Aromatic and aliphatic alkynyl ketones were converted into the corresponding 3-amino-2-pyrone derivatives in moderate to high yields. When methyl propiolate was submitted to the reaction, α,β-dehydroamino acids were formed in good

  已经开发了温和而有效的合成3-氨基-2-吡喃酮衍生物的方法。该方法基于将N-（二苯基亚甲基）甘氨酸盐迈克尔加成到各种炔基酮中，然后使用10mol％氢氧化钠作为催化剂进行内酯化。将芳族和脂族炔基酮以中等至高产率转化为相应的3-氨基-2-吡喃酮衍生物。当丙酸甲酯进行反应时，以良好的产率形成α，β-脱氢氨基酸。 3-氨基-2-吡喃酮衍生物-炔基酮-迈克尔加成-内酯化-合成
• Cycloaddition of Alkynyl Ketones with <i>N</i>-Tosylimines Catalyzed by Bu₃P and DMAP: Synthesis of Highly Functionalized Pyrrolidines and Azetidines
  作者：Ling-Guo Meng、Peijie Cai、Qingxiang Guo、Song Xue

  DOI：10.1021/jo801687v

  日期：2008.11.7

  Cycloadditions of alkynyl ketones with N-tosylimines catalyzed by Lewis bases to synthesize azetidines and pyrrolidines were systematically described. In the reaction of alkynyl ketones with N-tosylimines catalyzed by Bu3P at room temperature in toluene, highly functionalized pyrrolidines were formed in good to excellent yields. When DMAP was used in place of Bu3P as catalyst to facilitate the cycloaddition, completely substituted azetidines were produced in moderate to good yields in CH2Cl2. Both cyclization reactions proceeded smoothly with complete stereoselectivity. The scope and limitations of these cycloadditon reactions were also investigated.