3-methyl-1-(thiophen-2-yl)but-3-en-1-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-methyl-1-(thiophen-2-yl)but-3-en-1-one
• 英文别名: 3-Methyl-1-thiophen-2-ylbut-3-en-1-one
• 化学式: C₉H₁₀OS
• 分子量: 166.244
• InChiKey: PQZQEZPECZNDIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 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：
  45.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-methyl-1-(thiophen-2-yl)but-3-en-1-one 在 tris-(dibenzylideneacetone)dipalladium(0) 、 盐酸羟胺 、 (R)-N-((S)-(2-(di((3R,5R,7R)-adamantan-1-yl)phosphaneyl)-4,5-dimethoxyphenyl)(phenyl)methyl)-N,2-dimethylpropane-2-sulfinamide 、 sodium acetate 、 sodium t-butanolate 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 8.0h， 生成 (S)-5-benzyl-5-methyl-3-(thiophen-2-yl)-4,5-dihydroisoxazole
  参考文献：
  名称：

  钯催化烯基肟的碳醚化可实现异恶唑啉的对映选择性合成。

  摘要：

  此处报道的是高效率的Pd / Xiang-Phos催化的烯基肟与芳基或烯基卤化物的对映选择性碳醚化，可提供各种手性3,5-二取代和3,5,5-三取代的异恶唑啉，收率高达97％ 。体积大且富含电子的（S，Rs）-NMe-X2配体负责出色的反应性和对映选择性。该转化的显着特征包括温和的反应条件，一般的底物范围，良好的官能团耐受性，良好的收率，高对映选择性，易于扩大规模以及在生物活性化合物的后期修饰中的应用。所获得的产物可以容易地转化为有用的手性1，3-氨基醇。

  DOI：

  10.1002/anie.201912408
• 作为产物：
  描述：

  2-环丙基-1-(噻吩-2-基)乙烷-1-酮 在 Wilkinson's catalyst 作用下， 以 甲苯 为溶剂， 反应 55.0h， 生成 3-methyl-1-(thiophen-2-yl)but-3-en-1-one
  参考文献：
  名称：

  Selective, Catalytic Carbon−Carbon Bond Activation and Functionalization Promoted by Late Transition Metal Catalysts

  摘要：

  The selective catalytic activation and functionalization of carbon-carbon bonds in a series of substituted cyclopropane substrates has been developed using commercially available transition metal catalysts. Catalytic hydrogenation and olefination procedures, tolerant of a range of functional groups, have been discovered. Introduction of a chelate-assisting substituent such as [PPh2] is effective in altering the kinetic selectivity and lowering the activation barrier for the catalytic processes.

  DOI：

  10.1021/ja028912j

文献信息

• Accessing novel fluorinated heterocycles with the hypervalent fluoroiodane reagent by solution and mechanochemical synthesis
  作者：William Riley、Andrew C. Jones、Kuldip Singh、Duncan L. Browne、Alison M. Stuart

  DOI：10.1039/d1cc02587b

  日期：——

  A new and efficient strategy for the rapid formation of novel fluorinated tetrahydropyridazines and dihydrooxazines has been developed by fluorocyclisation of β,γ-unsaturated hydrazones and oximes with the fluoroiodane reagent. Mechanochemical synthesis delivered fluorinated tetrahydropyridazines in similar excellent yields to conventional solution synthesis, whereas fluorinated dihydrooxazines were

  通过用氟碘试剂对 β,γ-不饱和腙和肟进行氟环化，开发了一种快速形成新型氟化四氢哒嗪和二氢恶嗪的有效策略。机械化学合成以与常规溶液合成相似的优异产率提供氟化四氢哒嗪，而通过球磨制备氟化二氢恶嗪的产率要好得多。
• Copper-Catalyzed Aerobic 6-Endo-Trig Cyclization of β,γ-Unsaturated Hydrazones for the Divergent Synthesis of Dihydropyridazines and Pyridazines
  作者：Zhenwei Fan、Zhangjin Pan、Liangsen Huang、Jiajia Cheng

  DOI：10.1021/acs.joc.9b00228

  日期：2019.4.5

  A divergent synthetic strategy to 1,6-dihydropyridazines and pyridazines through Cu(II)-catalyzed controllable aerobic 6-endo-trig cyclization was developed. The selectivity can be rationally tuned via the judicious choice of reaction solvent. It was found that the 1,6-dihydropyridazines were obtained in moderate to high yields with CH3CN as the reaction solvent, whereas employment of AcOH directly

  通过Cu（II）催化可控的好氧6-endo-trig环化反应，开发了一种合成1,6-二氢哒嗪和哒嗪的合成策略。可以通过明智地选择反应溶剂来合理地调节选择性。已经发现，以CH 3 CN作为反应溶剂可以中等至高收率获得1,6-二氢哒嗪，而使用AcOH直接以高达92％的收率获得哒嗪，这可能是由于原位生成的氧化所致。 1,6-二氢哒嗪。
• Palladium-Catalyzed Oxime Assisted Intramolecular Dioxygenation of Alkenes with 1 atm of Air as the Sole Oxidant
  作者：Ming-Kui Zhu、Jun-Feng Zhao、Teck-Peng Loh

  DOI：10.1021/ja100716x

  日期：2010.5.12

  This paper describes a palladium-catalyzed oxime assisted intramolecular dioxygenation of alkenes by using 1 atm of air as the sole oxidant under extremely mild conditions, which demonstrated the feasibility of incorporating atmospheric oxygen into synthetically useful products under 1 atm of air at room temperature.
• Mn- and Co-Catalyzed Aminocyclizations of Unsaturated Hydrazones Providing a Broad Range of Functionalized Pyrazolines
  作者：Moritz Balkenhohl、Sebastian Kölbl、Tony Georgiev、Erick M. Carreira

  DOI：10.1021/jacsau.1c00176

  日期：2021.7.26
• Selective, Catalytic Carbon−Carbon Bond Activation and Functionalization Promoted by Late Transition Metal Catalysts
  作者：Suzanne C. Bart、Paul J. Chirik

  DOI：10.1021/ja028912j

  日期：2003.1.1

  The selective catalytic activation and functionalization of carbon-carbon bonds in a series of substituted cyclopropane substrates has been developed using commercially available transition metal catalysts. Catalytic hydrogenation and olefination procedures, tolerant of a range of functional groups, have been discovered. Introduction of a chelate-assisting substituent such as [PPh2] is effective in altering the kinetic selectivity and lowering the activation barrier for the catalytic processes.