(E)-3-(furan-2-yl)-1-(4-nonylisoxazol-3-yl)prop-2-en-1-one | 1332635-43-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-3-(furan-2-yl)-1-(4-nonylisoxazol-3-yl)prop-2-en-1-one
• 英文别名: (E)-3-(furan-2-yl)-1-(4-nonyl-1,2-oxazol-3-yl)prop-2-en-1-one
• CAS: 1332635-43-4
• 化学式: C₁₉H₂₅NO₃
• 分子量: 315.412
• InChiKey: PRSFFAWGKVRCJI-OUKQBFOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  23
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  56.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-3-(furan-2-yl)-1-(4-nonylisoxazol-3-yl)prop-2-en-1-one 在 正丁基锂 、 对甲苯磺酸 、 二异丙胺 、 lithium chloride 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 甲苯 为溶剂， 反应 46.5h， 生成 methyl 3-(furan-2-yl)-5-methoxy-2-(2-methoxy-2-oxoethyl)-5-(4-nonylisoxazol-3-yl)tetrahydrofuran-2-carboxylate
  参考文献：
  名称：

  Three-Component Coupling Approach to Trachyspic Acid

  摘要：

  Three-component coupling of the lithium enolate of t-BuOAc, silyl glyoxylate, and an alpha,beta-unsaturated ketone enables the rapid construction of the trachyspic acid carbon skeleton. A 3,4-disubstituted isoxazole is utilized to mask the C7/C9 dicarbonyl. New enolsilane/nitrile-oxide cycloadditions enable the preparation of various 3,4-disubstituted isoxazoles that are challenging to access by other means.

  DOI：

  10.1021/ol202002r
• 作为产物：
  描述：

  十一醛 在 正丁基锂 、 potassium carbonate 、 对甲苯磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 173.5h， 生成 (E)-3-(furan-2-yl)-1-(4-nonylisoxazol-3-yl)prop-2-en-1-one
  参考文献：
  名称：

  Three-Component Coupling Approach to Trachyspic Acid

  摘要：

  Three-component coupling of the lithium enolate of t-BuOAc, silyl glyoxylate, and an alpha,beta-unsaturated ketone enables the rapid construction of the trachyspic acid carbon skeleton. A 3,4-disubstituted isoxazole is utilized to mask the C7/C9 dicarbonyl. New enolsilane/nitrile-oxide cycloadditions enable the preparation of various 3,4-disubstituted isoxazoles that are challenging to access by other means.

  DOI：

  10.1021/ol202002r

文献信息

• Three-Component Glycolate Michael Reactions of Enolates, Silyl Glyoxylates, and α,β-Enones
  作者：Daniel C. Schmitt、Ericka J. Malow、Jeffrey S. Johnson

  DOI：10.1021/jo202679u

  日期：2012.4.6

  Silyl glyoxylates react with enolates and enones to afford either glycolate aldol or Michael adducts. Product identity is controlled by the countercation associated with the enolate. Reformatsky nucleophiles in the presence of additional Zn(OTf)(2) result in aldol coupling (A), while lithium enolates provide the Michael coupling (B). Deprotonation of the aldol product A with LDA induces equilibration to form the minor diastereomer of Michael product B. This observation suggests that formation of the major diastereomer of Michael product B does not occur via an aldol/retro-aldol/Michael sequence.
• Three-Component Coupling Approach to Trachyspic Acid
  作者：Daniel C. Schmitt、Leighann Lam、Jeffrey S. Johnson

  DOI：10.1021/ol202002r

  日期：2011.10.7

  Three-component coupling of the lithium enolate of t-BuOAc, silyl glyoxylate, and an alpha,beta-unsaturated ketone enables the rapid construction of the trachyspic acid carbon skeleton. A 3,4-disubstituted isoxazole is utilized to mask the C7/C9 dicarbonyl. New enolsilane/nitrile-oxide cycloadditions enable the preparation of various 3,4-disubstituted isoxazoles that are challenging to access by other means.