Ethyl 3-(5'-fluoro-2'-methylphenyl)propanoate | 137466-12-7

• 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 3-(5'-fluoro-2'-methylphenyl)propanoate
• 英文别名: Ethyl 3-(5'-fluoro-2'-methylphenyl)propionate；ethyl 3-(5-fluoro-2-methylphenyl)propanoate
• CAS: 137466-12-7
• 化学式: C₁₂H₁₅FO₂
• 分子量: 210.248
• InChiKey: UICLOBHJMACJSV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Ethyl 3-(5'-fluoro-2'-methylphenyl)propanoate 在 sodium hydroxide 作用下， 反应 0.13h， 生成 7-Fluoro-4-methyl-1-indanone
  参考文献：
  名称：

  Nuclear spin-spin coupling via nonbonded interactions. 7. Effects of molecular structure on nitrogen-fluorine coupling

  摘要：

  To test whether the recently discovered phenomenon of through-space nuclear spin-spin coupling between intramolecularly crowded N-15 and F-19 nuclei shows the same sort of striking dependence on molecular structure as the long-known phenomenon of through-space nuclear spin-spin coupling between pairs of intramolecularly crowded F-19 nuclei, several N-15-enriched oximes and some simple derivatives thereof were synthesized and their J(NF) values were determined by F-19 NMR spectroscopy. The experimental J(NF) values ranged from 8.6 to 43.5 Hz. The molecular structures of these compounds were determined by single-crystal X-ray diffraction. The observed dependence of the N-15-F-19 coupling constants on molecular structure was qualitatively consistent with the predictions of the lone-pair orbital overlap theory that was developed earlier to account for through-space coupling involving fluorine nuclei.

  DOI：

  10.1021/jo00027a063
• 作为产物：
  描述：

  Ethyl 3-(5-fluoro-2-methylphenyl)prop-2-enoate 在 氢气 作用下， 以 乙酸乙酯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 生成 Ethyl 3-(5'-fluoro-2'-methylphenyl)propanoate
  参考文献：
  名称：

  通过 I(I)/I(III) 催化二烯碳官能化锻造中环

  摘要：

  公开了一种基于 I(I)/I(III) 催化的策略，通过 2-苯乙基取代的 1,3-二烯的直接碳官能化来获得 8 元碳环。这种生成密集功能化氟化苯并环辛烯的策略是模块化的，通过氧化/活化机制和外部亲核试剂的变化，具有挑战性的环化可以与烯丙基 C−O、C−N 和 C−C 键的形成合并（> 30 个例子）。

  DOI：

  10.1002/anie.202309789

文献信息

• Nuclear spin-spin coupling via nonbonded interactions. 7. Effects of molecular structure on nitrogen-fluorine coupling
  作者：Frank B. Mallory、Eddie D. Luzik、Clelia W. Mallory、Patrick J. Carroll

  DOI：10.1021/jo00027a063

  日期：1992.1

  To test whether the recently discovered phenomenon of through-space nuclear spin-spin coupling between intramolecularly crowded N-15 and F-19 nuclei shows the same sort of striking dependence on molecular structure as the long-known phenomenon of through-space nuclear spin-spin coupling between pairs of intramolecularly crowded F-19 nuclei, several N-15-enriched oximes and some simple derivatives thereof were synthesized and their J(NF) values were determined by F-19 NMR spectroscopy. The experimental J(NF) values ranged from 8.6 to 43.5 Hz. The molecular structures of these compounds were determined by single-crystal X-ray diffraction. The observed dependence of the N-15-F-19 coupling constants on molecular structure was qualitatively consistent with the predictions of the lone-pair orbital overlap theory that was developed earlier to account for through-space coupling involving fluorine nuclei.
• Forging Medium Rings via I(I)/I(III)‐Catalyzed Diene Carbofunctionalization
  作者：You‐Jie Yu、Joel Häfliger、Zi‐Xuan Wang、Constantin G. Daniliuc、Ryan Gilmour

  DOI：10.1002/anie.202309789

  日期：2023.9.18

  An I(I)/I(III) catalysis-based strategy to access 8-membered carbocycles via the direct carbofunctionalization of 2-phenethyl-substituted 1,3-dienes is disclosed. This strategy to generate densely functionalized, fluorinated benzocyclooctenes is modular and through changes in the oxidation/activation regime and the external nucleophile, the challenging cyclization can be merged with formation of allylic

  公开了一种基于 I(I)/I(III) 催化的策略，通过 2-苯乙基取代的 1,3-二烯的直接碳官能化来获得 8 元碳环。这种生成密集功能化氟化苯并环辛烯的策略是模块化的，通过氧化/活化机制和外部亲核试剂的变化，具有挑战性的环化可以与烯丙基 C−O、C−N 和 C−C 键的形成合并（> 30 个例子）。