2-[2-(4-fluorophenyl)-2-oxoethoxy]benzaldehyde | 1108233-61-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-[2-(4-fluorophenyl)-2-oxoethoxy]benzaldehyde
• 英文别名: 2-[2-(4-Fluorophenyl)-2-oxoethoxy]benzaldehyde
• CAS: 1108233-61-9
• 化学式: C₁₅H₁₁FO₃
• 分子量: 258.249
• InChiKey: HGJOHMFFWIVNPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[2-(4-fluorophenyl)-2-oxoethoxy]benzaldehyde 在 (5aR,6R,9S,9aS)-6,11,11-trimethyl-2-(2,4,6-trichlorophenyl)-5a,6,7,8,9,9a-hexahydro-4H-6,9-methanobenzo[b][1,2,4]-triazolo[4,3-d][1,4]oxazin-2-ium tetraphenylborate 、 N,N-二异丙基乙胺 作用下， 反应 20.0h， 以81%的产率得到(S)-3-(4-fluorophenyl)-3-hydroxychroman-4-one
  参考文献：
  名称：

  Enantioselective Synthesis of Chromanones Bearing Quaternary Substituted Stereocenters Catalyzed by (1R)-Camphor-Derived N-Heterocyclic Carbenes

  摘要：

  A catalytic asymmetric intramolecular crossed-benzoin reaction for the synthesis of chromanones by novel camphor-derived N-heterocyclic carbenes is described. The corresponding chromanones bearing quaternary stereogenic centers were isolated in high yields with high to excellent enantioselectivity.

  DOI：

  10.1021/acs.joc.5b01029
• 作为产物：
  描述：

  2-(2-hydroxyphenyl)-1,3-dithiane 在 mercury(II) trifluoroacetate 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 2-[2-(4-fluorophenyl)-2-oxoethoxy]benzaldehyde
  参考文献：
  名称：

  Enantioselective Synthesis of Chromanones Bearing Quaternary Substituted Stereocenters Catalyzed by (1R)-Camphor-Derived N-Heterocyclic Carbenes

  摘要：

  A catalytic asymmetric intramolecular crossed-benzoin reaction for the synthesis of chromanones by novel camphor-derived N-heterocyclic carbenes is described. The corresponding chromanones bearing quaternary stereogenic centers were isolated in high yields with high to excellent enantioselectivity.

  DOI：

  10.1021/acs.joc.5b01029

文献信息

• Copper-Catalyzed Intramolecular Aldehyde–Ketone Nucleophilic Additions for the Synthesis of Chromans Bearing a Tertiary Alcohol Motif
  作者：Chenghao Zhu、Wenbo Jiang、Da Ma

  DOI：10.1021/acs.joc.3c02365

  日期：2024.1.19

  The synthesis of chroman-3-ol derivatives via intramolecular nucleophilic additions has been established. Aldehydes can be used as alkyl carbanion equivalents via reductive polarity reversal which is facilitated by a copper catalyst and N-heterocyclic carbene ligand under mild conditions. The key to success is the difference in reaction activity between aldehydes and ketones. Finally, this methodology

  已经建立了通过分子内亲核加成合成色满-3-醇衍生物的方法。通过铜催化剂和 N-杂环卡宾配体在温和条件下促进还原极性反转，醛可用作烷基碳负离子等价物。成功的关键是醛和酮之间反应活性的差异。最后，该方法还可用于构建含有叔醇的其他环状结构，包括四氢化萘、环己烷、茚满和9,10-二氢菲。
• Shen, Zengming; Dornan, Peter K.; Khan, Hasan A., Journal of the American Chemical Society, 2009, vol. 131, p. 1077 - 1091
  作者：Shen, Zengming、Dornan, Peter K.、Khan, Hasan A.、Woo, Tom K.、Dong, Vy M.

  DOI：——

  日期：——
• Enantioselective Synthesis of Chromanones Bearing Quaternary Substituted Stereocenters Catalyzed by (1<i>R</i>)-Camphor-Derived <i>N</i>-Heterocyclic Carbenes
  作者：Zbigniew Rafiński、Anna Kozakiewicz

  DOI：10.1021/acs.joc.5b01029

  日期：2015.8.7

  A catalytic asymmetric intramolecular crossed-benzoin reaction for the synthesis of chromanones by novel camphor-derived N-heterocyclic carbenes is described. The corresponding chromanones bearing quaternary stereogenic centers were isolated in high yields with high to excellent enantioselectivity.