1-phenyl-2-(thiophen-3-yl)propan-1-one | 873335-99-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-phenyl-2-(thiophen-3-yl)propan-1-one
• 英文别名: 1-phenyl-2-thiophen-3-ylpropan-1-one
• CAS: 873335-99-0
• 化学式: C₁₃H₁₂OS
• 分子量: 216.304
• InChiKey: IAHNFQYFPIRIES-UHFFFAOYSA-N

物化性质

• 沸点：
  338.0±17.0 °C(Predicted)
• 密度：
  1.148±0.06 g/cm3(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：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  45.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-氯噻吩 、 苯丙酮 在 (N,N'-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)Pd(OAc)2 sodium t-butanolate 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以36%的产率得到1-phenyl-2-(thiophen-3-yl)propan-1-one
  参考文献：
  名称：

  由咪唑-2-亚甲基钯（乙酸）体系介导的酮的α-芳基化反应的温和有效方案

  摘要：

  在酮的α-芳基化中已经研究了定义明确的N-杂环卡宾（NHC）-乙酸钯络合物的活性。烯醇盐是通过使用略微过量的叔丁醇钠作为碱原位生成的。结果显示出高活性，允许偶联未活化的氯化物。受阻底物的使用提供了便利合成各种酮衍生物的途径。还介绍了由NHC连接的催化剂介导的酮在室温下α-芳基化的第一个例子。

  DOI：

  10.1016/j.jorganchem.2005.07.083

文献信息

• Preparation and Application of Solid, Salt-Stabilized Zinc Amide Enolates with Enhanced Air and Moisture Stability
  作者：Yi-Hung Chen、Mario Ellwart、Georgios Toupalas、Yusuke Ebe、Paul Knochel

  DOI：10.1002/anie.201700216

  日期：2017.4.10

  various N‐morpholino amides with TMPZnCl⋅LiCl (TMP=2,2,6,6‐tetramethylpiperidyl) and Mg(OPiv)2 in THF at 25 °C provides solid zinc enolates with enhanced air and moisture stability (t1/2 in air: 1–3 h) after solvent evaporation. These enolates undergo Pd‐ and Cu‐catalyzed cross‐couplings with (hetero)aryl bromides as well as allylic and benzylic halides. The arylated N‐morpholino amides were converted into

  在25°C下用TMPZnCl⋅LiCl（TMP = 2,2,6,6-四甲基哌啶基）和Mg（OPiv）2在THF中处理各种N-吗啉代酰胺可提供具有增强的空气和湿气稳定性的固体烯醇锌（t 1溶剂蒸发后，在空气中/ 2（1-3小时）。这些烯醇化物与（杂）芳基溴化物以及烯丙基和苄基卤化物经历钯和铜催化的交叉偶联。所述芳基化的N-吗啉代酰胺通过的LaCl转化成各种酮3 ⋅2的LiCl介导的酰基化以格氏试剂。新的固体烯醇化物被用来分六个步骤制备有效的抗乳腺癌药物候选物，总产率为23％。
• Copper-Catalyzed Regioselective Reaction of Internal Alkynes and Diaryliodonium Salts
  作者：Ze-Feng Xu、Chen-Xin Cai、Jin-Tao Liu

  DOI：10.1021/ol4003543

  日期：2013.5.3

  The copper-catalyzed highly regioselective reaction of internal alkynes with diaryliodonium salts was achieved for the first time. α-Arylketones were obtained in moderate to good yields from arylpropargylic alcohols or aryl alkyl alkynes under mild conditions. It was found that the two kinds of substrates underwent two different arylation–oxygenation pathways under different reaction conditions based

  首次实现了内部炔烃与二芳基碘鎓盐的铜催化的高度区域选择性反应。在温和的条件下，从芳基炔丙醇或芳基烷基炔烃以中等至良好的产率获得α-芳基酮。基于氘代实验，控制实验和反应中间体的光谱分析，发现两种底物在不同的反应条件下经历了两种不同的芳构化-加氧途径。
• Palladium-Catalyzed α-Arylation of Arylketones at Low Catalyst Loadings
  作者：Enrico Marelli、Martin Corpet、Sian R. Davies、Steven P. Nolan

  DOI：10.1002/chem.201404900

  日期：2014.12.22

  involves the use of a preformed, bench‐stable Pd–N‐heterocyclic carbene pre‐catalyst bearing IHept as an ancillary ligand, and allows the coupling of various functionalized coupling partners at very low catalyst loading. Careful choice of the solvent/base system was crucial to obtain optimum catalyst performance. The pre‐catalyst was also successfully tested in the synthesis of an industrially relevant

  已经开发出用于芳基酮α-芳基化的一般催化方案。它涉及使用预成型的，板凳稳定的Pd– N杂环卡宾预催化剂作为辅助配体，并允许在非常低的催化剂负载量下偶联各种官能化的偶联伙伴。仔细选择溶剂/碱体系对于获得最佳催化剂性能至关重要。在合成工业上有用的化合物时，也成功地测试了前催化剂。
• An efficient and mild protocol for the α-arylation of ketones mediated by an (imidazol-2-ylidene)palladium(acetate) system
  作者：Rohit Singh、Steven P. Nolan

  DOI：10.1016/j.jorganchem.2005.07.083

  日期：2005.12

  complexes has been studied in the α-arylation of ketones. The enolate was generated in situ via use of slight excess of sodium tert-butoxide as base. The results showed a high activity, allowing for the coupling of non-activated chlorides. The use of hindered substrates provided an avenue for convenient synthesis of various ketone derivatives. The first examples of α-arylation of ketones at room temperature

  在酮的α-芳基化中已经研究了定义明确的N-杂环卡宾（NHC）-乙酸钯络合物的活性。烯醇盐是通过使用略微过量的叔丁醇钠作为碱原位生成的。结果显示出高活性，允许偶联未活化的氯化物。受阻底物的使用提供了便利合成各种酮衍生物的途径。还介绍了由NHC连接的催化剂介导的酮在室温下α-芳基化的第一个例子。
• A Highly Practical and General Route for α-Arylations of Ketones Using Bis-phosphinoferrocene-Based Palladium Catalysts
  作者：Gabriela A. Grasa、Thomas J. Colacot

  DOI：10.1021/op7002503

  日期：2008.5.1

  Well-defined, air-stable Pd complexes of bis-phosphinoferrocene family of catalysts have been studied in the arylation of various ketones with aryl chlorides and aryl bromides. Bis(di-tert-butyl)phosphinoferrocene (DtBPF)-based catalysts such as (DtBPF) PdCl2 and (DtBPF)PdBr2 have been identified as two of the most active catalysts for the alpha-arylation of a model reaction involving propiophenone and 4-chlorotoluene. The scope of the (DtBPF)PdCl2 catalyst has been efficiently expanded to the arylation of various ketones with aryl chlorides and bromides with up to 97% isolated yields, under relatively mild reaction conditions at low catalyst loadings. The efficacy of the (DtBPF)PdCl2 catalyst was demonstrated at very low catalyst loadings with SIC 10,000 for the difficult aryl bromide, 4-bromoanisole, and 2000 for the electron-neutral aryl chloride, 4-chlorotoluene, on similar to 10-g scale with excellent isolated yields and lower Pd in the product (6 and 48 ppm, respectively). Comparative studies on the Pd:DtBPF molar ratios between in situ catalysts and preisolated catalysts revealed that preisolated (DtBPF)PdX2 (X = Cl, Br) are the catalysts of choice due to various practical reasons.