3-carbethoxy-4,5-dihydro-2-phenyl-5-methylenefuran | 122132-59-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 3-carbethoxy-4,5-dihydro-2-phenyl-5-methylenefuran
• 英文别名: ethyl 2-methylidene-5-phenyl-3H-furan-4-carboxylate
• CAS: 122132-59-6
• 化学式: C₁₄H₁₄O₃
• 分子量: 230.263
• InChiKey: PROJLOGCQFCTQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-carbethoxy-4,5-dihydro-2-phenyl-5-methylenefuran 在 Amberlist 作用下， 以 苯 为溶剂， 反应 4.0h， 以71%的产率得到ethyl 5-methyl-2-phenylfuran-3-carboxylate
  参考文献：
  名称：

  Elimination reactions of terminal .beta.-oxy selenoxides. Synthesis of aryl and vinyl enol ethers and of furans, oxazoles, and thiazoles

  摘要：

  Elimination reactions of terminal selenoxides holding an alkoxy group in the beta position, RCH-(OR)CH2SeOPh, are usually difficult and can give rise to complex reaction mixtures. We report that these reactions take place more easily whenever the oxygen atom is linked to an unsaturated group (-CH=CHR, -Ar, -CR=O, -CH=NR). These selenoxides are easily available, and the elimination reaction was employed to effect useful syntheses of both open-chain and cyclic aryl and vinyl enol ethers. Moreover, by simple isomerization with acids or bases the cyclic derivatives can be transformed into the corresponding furans. The same procedure has been employed to synthesize substituted oxazoles and thiazoles also.

  DOI：

  10.1021/jo00058a011
• 作为产物：
  描述：

  ethyl 2-benzoylpent-4-enoate 在 ammonium peroxydisulfate 、 双氧水 、 碳酸氢钠 作用下， 以 甲醇 、 苯 为溶剂， 反应 25.0h， 生成 3-carbethoxy-4,5-dihydro-2-phenyl-5-methylenefuran
  参考文献：
  名称：

  Elimination reactions of terminal .beta.-oxy selenoxides. Synthesis of aryl and vinyl enol ethers and of furans, oxazoles, and thiazoles

  摘要：

  Elimination reactions of terminal selenoxides holding an alkoxy group in the beta position, RCH-(OR)CH2SeOPh, are usually difficult and can give rise to complex reaction mixtures. We report that these reactions take place more easily whenever the oxygen atom is linked to an unsaturated group (-CH=CHR, -Ar, -CR=O, -CH=NR). These selenoxides are easily available, and the elimination reaction was employed to effect useful syntheses of both open-chain and cyclic aryl and vinyl enol ethers. Moreover, by simple isomerization with acids or bases the cyclic derivatives can be transformed into the corresponding furans. The same procedure has been employed to synthesize substituted oxazoles and thiazoles also.

  DOI：

  10.1021/jo00058a011

文献信息

• Copper(I)-Catalyzed Dearomative (3 + 2) Cycloaddition of 3-Nitroindoles with Propargylic Nucleophiles: An Access to Cyclopenta[<i>b</i>]indolines
  作者：Johanne Ling、David Mara、Baptiste Roure、Maxime Laugeois、Maxime R. Vitale

  DOI：10.1021/acs.joc.9b03459

  日期：2020.3.6

  The copper(I)-catalyzed dearomatization of 3-nitroindoles with propargylic nucleophiles is described. In mild reaction conditions, this original dearomative (3 + 2) cycloaddition process gives access to a wide variety of cyclopenta[b]indolines in good to excellent yields, with high functional group tolerance. The proof of concept that an enantioselective version of this reaction is accessible by employing

  描述了用炔丙基亲核试剂的3-硝基吲哚的铜（I）催化的脱芳香化作用。在温和的反应条件下，这种原始的脱芳香性（3 + 2）环加成工艺可以高收率获得优异的收率，并具有很高的官能团耐受性，从而可以得到各种环戊[b]吲哚啉。获得了通过使用手性磷配体可获得该反应的对映选择性形式的概念证明。根据动力学研究给出了机理建议。
• Construction of Chiral Quaternary Carbon Centers via Asymmetric Metal Carbene <i>gem</i>‐Dialkylation
  作者：Shanliang Dong、Kemiao Hong、Zhijing Zhang、Jingjing Huang、Xiongda Xie、Haoxuan Yuan、Wenhao Hu、Xinfang Xu

  DOI：10.1002/anie.202302371

  日期：2023.6.26

  An enantioselective three-component reaction of α-diazo ketones with alkenes and 1,3,5-triazines is reported, which leads to poly-functionalized chiral ketones with excellent enantioselectivity. This unprecedented metal carbene gem-dialkylation reaction features a cascade formal asymmetric allylation and aminomethylation process with concomitant construction of all-carbon quaternary stereocenters using

  报道了 α-重氮酮与烯烃和 1,3,5-三嗪的对映选择性三组分反应，这导致了具有优异对映选择性的多官能化手性酮。这种前所未有的金属卡宾宝石二烷基化反应具有级联的形式不对称烯丙基化和氨甲基化过程，同时使用现成的材料构建全碳季立构中心。
• ANTONIOLETTI, R.;BONADIES, F.;SCETTRI, A., TETRAHEDRON LETT., 29,(1988) N 39, C. 4987-4990
  作者：ANTONIOLETTI, R.、BONADIES, F.、SCETTRI, A.

  DOI：——

  日期：——
• Elimination reactions of terminal .beta.-oxy selenoxides. Synthesis of aryl and vinyl enol ethers and of furans, oxazoles, and thiazoles
  作者：Marcello Tiecco、Lorenzo Testaferri、Marco Tingoli、Francesca Marini

  DOI：10.1021/jo00058a011

  日期：1993.3

  Elimination reactions of terminal selenoxides holding an alkoxy group in the beta position, RCH-(OR)CH2SeOPh, are usually difficult and can give rise to complex reaction mixtures. We report that these reactions take place more easily whenever the oxygen atom is linked to an unsaturated group (-CH=CHR, -Ar, -CR=O, -CH=NR). These selenoxides are easily available, and the elimination reaction was employed to effect useful syntheses of both open-chain and cyclic aryl and vinyl enol ethers. Moreover, by simple isomerization with acids or bases the cyclic derivatives can be transformed into the corresponding furans. The same procedure has been employed to synthesize substituted oxazoles and thiazoles also.