5-phenethylfuran-2-carbaldehyde | 52341-99-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-phenethylfuran-2-carbaldehyde
• 英文别名: 5-phenethyl-furan-2-carbaldehyde；5-Phenethyl-furfural；5-(2-Phenylethyl)furan-2-carbaldehyde
• CAS: 52341-99-8
• 化学式: C₁₃H₁₂O₂
• 分子量: 200.237
• InChiKey: SWMCAUGXMJUQNG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-phenethylfuran-2-carbaldehyde 在 sodium hydroxide 、 磷酸 、 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 2.25h， 生成 2-Acetonyl-5-β-phenethylfuran
  参考文献：
  名称：

  Cabares, Jacques; Mavoungou-Gomes, Louis, Bulletin de la Societe Chimique de France, 1986, # 3, p. 401 - 412

  摘要：

  DOI：
• 作为产物：
  描述：

  苯基膦酸二乙酯 在 sodium ethanolate 、 magnesium 、 三氯氧磷 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 39.0h， 生成 5-phenethylfuran-2-carbaldehyde
  参考文献：
  名称：

  Cabares, Jacques; Mavoungou-Gomes, Louis, Bulletin de la Societe Chimique de France, 1986, # 3, p. 401 - 412

  摘要：

  DOI：

文献信息

• Cobalt(II)-catalyzed preparation of alkylindium reagents and applications in cross-coupling with aryl halides
  作者：Peng Wang、Xuan-Di Song、Bing-Zhi Chen、Weidong Rao、Zhi-Liang Shen

  DOI：10.1016/j.catcom.2019.105824

  日期：2019.12

  The direct insertion of indium powder into alkyl iodides was found to be efficiently catalyzed by a catalytic amount of cobalt(II) bromide (10 mol%). Upon subjection of the thus-formed alkylindium compounds to palladium-catalyzed cross-coupling reactions with a wide range of aryl halides, a series of cross-coupled products could be obtained in moderate to good yields with the tolerance to many important

  发现通过催化量的溴化钴（II）（10mol％）可有效地催化将铟粉直接插入到烷基碘中。使如此形成的烷基铟化合物与钯与多种芳基卤化物进行交叉偶联反应后，可以以中等到良好的产率获得一系列交叉偶联的产物，并且对许多重要的官能团具有耐受性。
• Preparation of Alkyl Indium Reagents by Iodine-Catalyzed Direct Indium Insertion and Their Applications in Cross-Coupling Reactions
  作者：Man-Ling Zhi、Bing-Zhi Chen、Wei Deng、Xue-Qiang Chu、Teck-Peng Loh、Zhi-Liang Shen

  DOI：10.1021/acs.joc.9b00204

  日期：2019.3.1

  means of an iodine-catalyzed direct indium insertion into alkyl iodide in THF is reported. The thus-generated alkyl indium reagents effectively underwent Pd-catalyzed cross-coupling reactions with various aryl halides, exhibiting good compatibility to a variety of sensitive functional groups. By replacing THF with DMA and using 0.75 equiv of iodine, less reactive alkyl bromide could be used as substrate

  报道了一种通过碘催化的将铟直接插入到THF中的烷基碘中来合成烷基铟试剂的有效方法。如此生成的烷基铟试剂可有效地与各种芳基卤化物进行Pd催化的交叉偶联反应，表现出与各种敏感官能团的良好相容性。通过用DMA代替THF并使用0.75当量的碘，同等容易程度的反应性较低的烷基溴可以用作铟插入的底物。
• Direct Synthesis of Water-Tolerant Alkyl Indium Reagents and Their Application in Palladium-Catalyzed Couplings with Aryl Halides
  作者：Zhi-Liang Shen、Kelvin Kau Kiat Goh、Yong-Sheng Yang、Yin-Chang Lai、Colin Hong An Wong、Hao-Lun Cheong、Teck-Peng Loh

  DOI：10.1002/anie.201005798

  日期：2011.1.10

  A direct result: Alkyl indium reagents are synthesized by the insertion of indium into alkyl halide mediated by CuCl. The synthetic utility of these reagents is demonstrated by their palladium‐catalyzed coupling with aryl halides (see scheme). The reagents are compatible with various functional groups, and this makes the protocol generally useful in organic synthesis. DMA=N,N‐dimethylacetamide, TB

  直接结果：烷基铟试剂是通过将铟插入由CuCl介导的烷基卤中而合成的。这些试剂的合成实用性通过其钯催化与芳基卤化物的偶联来证明（参见方案）。该试剂可与各种官能团兼容，因此该方案通常可用于有机合成。DMA = N，N-二甲基乙酰胺，TBS =叔丁基二甲基甲硅烷基。
• Copper(II)-catalyzed preparation of alkylindium compounds and applications in cross-coupling reactions both in aqueous media
  作者：Peng Wang、Bing-Zhi Chen、Yi-Cong Guo、Weidong Rao、Zhi-Liang Shen

  DOI：10.1016/j.tetlet.2019.151288

  日期：2019.12

  effectively underwent palladium-catalyzed cross-coupling reactions with a myriad of aryl halides in aqueous media, leading to the cross-coupled products in modest to high yields. The mildness of the formed alkyl organometallics allowed the tolerance to various important functional groups incorporated in both substrates of alkyl iodides and aryl halides.

  开发了一种在催化量的廉价易得的CuSO 4 ·5H 2 O（10 mol％）存在下合成烷基铟化合物的高效水基方法。如此生成的烷基铟化合物与钯在水性介质中的芳基卤化物有效地进行了钯催化的交叉偶联反应，从而导致了中等至高收率的交叉偶联产物。所形成的烷基有机金属的温和性允许耐受结合在烷基碘和芳基卤的两种底物中的各种重要的官能团。
• Cesium carbonate‐catalyzed indium insertion into alkyl iodides and their synthetic utilities in cross‐coupling reactions
  作者：Xue‐Xin Feng、Zhen Wu、Qing‐Dong Wang、Bing‐Zhi Chen、Weidong Rao、Jin‐Ming Yang、Zhi‐Liang Shen

  DOI：10.1002/aoc.5110

  日期：——

  catalytic amount of cesium carbonate (10 mol%) was found to be capable of effectively catalyzing the insertion of indium powder into alkyl iodides. The thus‐generated alkyl indium reagents could readily undergo palladium‐catalyzed cross‐coupling reactions with a wide variety of aryl halides, showing compatibility to a range of important functional groups.

  发现催化量的碳酸铯（10mol％）能够有效地催化铟粉插入到烷基碘中。这样生成的烷基铟试剂可以很容易地与多种芳基卤化物进行钯催化的交叉偶联反应，显示出与一系列重要官能团的相容性。