ethyl 2-methoxyphenyl ketene | 1073529-33-5

• 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: ethyl 2-methoxyphenyl ketene
• 英文别名: o-anisyl ethyl ketene；2-methoxyphenyl ethyl ketene
• CAS: 1073529-33-5
• 化学式: C₁₁H₁₂O₂
• 分子量: 176.215
• InChiKey: UURGMTFTOQGBTG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  ethyl 2-methoxyphenyl ketene 、 1-苄基-1H-吲哚-2,3-二酮 在 C₃₉H₆₀N₄O₄ 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 1-benzyl-3'-ethyl-3'-(2-methoxyphenyl)spiro[indoline-3,2'-oxetane]-2,4'-dione
  参考文献：
  名称：

  Chiral Lewis Acid Catalyzed Asymmetric Cycloadditions of Disubstituted Ketenes for the Synthesis of β-Lactones and δ-Lactones

  摘要：

  Highly diastereo- and enantioselective [2 + 2]- and [4 + 2]-cycloadditions of disubstituted ketenes were realized by chiral Lewis acid catalysis. A series of arylalkylketenes underwent the reaction smoothly with isatins and beta,gamma-unsaturated alpha-ketoesters, providing optically active beta-lactones and delta-lactones with vicinal chiral centers in excellent yields (up to 99%) and enantioselectivities (up to 99% ee), as well as exclusively high diastereoselectivities under 0.2-2 mol % catalyst loading.

  DOI：

  10.1021/ol4031217
• 作为产物：
  描述：

  2-(2-甲氧基苯基)丁酰氯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以48%的产率得到ethyl 2-methoxyphenyl ketene
  参考文献：
  名称：

  NHC促进立体异构和化学扩散的芳烷基烯酮与氯的官能化

  摘要：

  用N-杂环卡宾处理烷基芳基烯酮和三氯乙醛（氯代）时，观察到立体和化学发散对映选择性反应途径，选择性地产生β-内酯（高达88:12 dr，高达94％  ee）或α-氯代酯（高达至94％  ee）。乙烯酮中的2-芳基取代或α-支链的i Pr烷基取代基都有利于氯化途径，从而使氯醛可以在不对称催化中用作亲电子氯化试剂。

  DOI：

  10.1002/chem.201503308

文献信息

• Enantioselective Nucleophilic Catalysis: The Synthesis of Aza-β-Lactams through [2+2] Cycloadditions of Ketenes with Azo Compounds
  作者：Jacob M. Berlin、Gregory C. Fu

  DOI：10.1002/anie.200802439

  日期：2008.9.1
• Dochnahl, Maximilian; Fu, Gregory C., Angewandte Chemie - International Edition, 2009, vol. 48, p. 2391 - 2393
  作者：Dochnahl, Maximilian、Fu, Gregory C.

  DOI：——

  日期：——
• Chiral Lewis Acid Catalyzed Asymmetric Cycloadditions of Disubstituted Ketenes for the Synthesis of β-Lactones and δ-Lactones
  作者：Xiaoyu Hao、Xiaohua Liu、Wei Li、Fei Tan、Yangyang Chu、Xiaohu Zhao、Lili Lin、Xiaoming Feng

  DOI：10.1021/ol4031217

  日期：2014.1.3

  Highly diastereo- and enantioselective [2 + 2]- and [4 + 2]-cycloadditions of disubstituted ketenes were realized by chiral Lewis acid catalysis. A series of arylalkylketenes underwent the reaction smoothly with isatins and beta,gamma-unsaturated alpha-ketoesters, providing optically active beta-lactones and delta-lactones with vicinal chiral centers in excellent yields (up to 99%) and enantioselectivities (up to 99% ee), as well as exclusively high diastereoselectivities under 0.2-2 mol % catalyst loading.
• Stereo‐ and Chemodivergent NHC‐Promoted Functionalisation of Arylalkylketenes with Chloral
  作者：James J. Douglas、Gwydion Churchill、Alexandra M. Z. Slawin、David J. Fox、Andrew D. Smith

  DOI：10.1002/chem.201503308

  日期：2015.11.9

  Stereo‐ and chemodivergent enantioselective reaction pathways are observed upon treatment of alkylarylketenes and trichloroacetaldehyde (chloral) with N‐heterocyclic carbenes, giving selectively either β‐lactones (up to 88:12 dr, up to 94 % ee) or α‐chloroesters (up to 94 % ee). Either 2‐arylsubstitution or an α‐branched iPr alkyl substituent within the ketene favours the chlorination pathway, allowing

  用N-杂环卡宾处理烷基芳基烯酮和三氯乙醛（氯代）时，观察到立体和化学发散对映选择性反应途径，选择性地产生β-内酯（高达88:12 dr，高达94％  ee）或α-氯代酯（高达至94％  ee）。乙烯酮中的2-芳基取代或α-支链的i Pr烷基取代基都有利于氯化途径，从而使氯醛可以在不对称催化中用作亲电子氯化试剂。