7-甲酰基-5-甲氧基-2,3-二氢苯并呋喃 | 156297-76-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 中文名称: 7-甲酰基-5-甲氧基-2,3-二氢苯并呋喃
• 英文名称: 7-Formyl-5-methoxy-2,3-dihydrobenzofuran
• 英文别名: 5-Methoxy-2,3-dihydro-1-benzofuran-7-carbaldehyde
• CAS: 156297-76-6
• 化学式: C₁₀H₁₀O₃
• 分子量: 178.188
• InChiKey: HOBMENQWVAUXNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  7-甲酰基-5-甲氧基-2,3-二氢苯并呋喃 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 0.08h， 以77%的产率得到2,3-Dihydro-5-methoxy-7-benzofuranmethanol
  参考文献：
  名称：

  Relevance of Conformational Constraints to the Regioselective Lithiation of Aromatic Diethers. Application to the Convenient Construction of the DEF Tricyclic Subunit of the Austalides

  摘要：

  The lithiation of 29 and 30 is shown to occur at all three sites with a dissimilar kinetic preference. For the dihydrofuran, reaction at the proton labeled H-beta, operates predominantly; in the dihydropyran example, H-alpha is the favored site of deprotonation. These protons represent those that are the most deshielded in the respective H-1 NMR spectra. The same is true for 9 and 19, both of which undergo metalation adjacent to the ring oxygen. No crossover in regioselectivity is observed, presumably because the methoxy substituent is sterically precluded from rotating freely. Mixed complexes (dimers, etc.) or mixed aggregates in low equilibrium concentration are key to understanding the acidification phenomenon of ortho hydrogens. As a consequence of the dominance of regiocontrol by the ring oxygen in 9, a convenient means has been developed for elaboration of the tricyclic eastern sector of the austalide mycotoxins.

  DOI：

  10.1021/jo00087a018
• 作为产物：
  描述：

  2-bromo-1-(2-chloroethoxy)-4-methoxybenzene 在 正丁基锂 、 四甲基乙二胺 、 magnesium 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 1.5h， 生成 7-甲酰基-5-甲氧基-2,3-二氢苯并呋喃
  参考文献：
  名称：

  Relevance of Conformational Constraints to the Regioselective Lithiation of Aromatic Diethers. Application to the Convenient Construction of the DEF Tricyclic Subunit of the Austalides

  摘要：

  The lithiation of 29 and 30 is shown to occur at all three sites with a dissimilar kinetic preference. For the dihydrofuran, reaction at the proton labeled H-beta, operates predominantly; in the dihydropyran example, H-alpha is the favored site of deprotonation. These protons represent those that are the most deshielded in the respective H-1 NMR spectra. The same is true for 9 and 19, both of which undergo metalation adjacent to the ring oxygen. No crossover in regioselectivity is observed, presumably because the methoxy substituent is sterically precluded from rotating freely. Mixed complexes (dimers, etc.) or mixed aggregates in low equilibrium concentration are key to understanding the acidification phenomenon of ortho hydrogens. As a consequence of the dominance of regiocontrol by the ring oxygen in 9, a convenient means has been developed for elaboration of the tricyclic eastern sector of the austalide mycotoxins.

  DOI：

  10.1021/jo00087a018

文献信息

• Relevance of Conformational Constraints to the Regioselective Lithiation of Aromatic Diethers. Application to the Convenient Construction of the DEF Tricyclic Subunit of the Austalides
  作者：Leo A. Paquette、Matthias M. Schulze、David G. Bolin

  DOI：10.1021/jo00087a018

  日期：1994.4

  The lithiation of 29 and 30 is shown to occur at all three sites with a dissimilar kinetic preference. For the dihydrofuran, reaction at the proton labeled H-beta, operates predominantly; in the dihydropyran example, H-alpha is the favored site of deprotonation. These protons represent those that are the most deshielded in the respective H-1 NMR spectra. The same is true for 9 and 19, both of which undergo metalation adjacent to the ring oxygen. No crossover in regioselectivity is observed, presumably because the methoxy substituent is sterically precluded from rotating freely. Mixed complexes (dimers, etc.) or mixed aggregates in low equilibrium concentration are key to understanding the acidification phenomenon of ortho hydrogens. As a consequence of the dominance of regiocontrol by the ring oxygen in 9, a convenient means has been developed for elaboration of the tricyclic eastern sector of the austalide mycotoxins.