3-(4-fluorobenzyl)-3-hydroxy-2-methylisoindolin-1-one | 1197385-26-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 3-(4-fluorobenzyl)-3-hydroxy-2-methylisoindolin-1-one
• CAS: 1197385-26-4
• 化学式: C₁₆H₁₄FNO₂
• 分子量: 271.291
• InChiKey: LARMIXJQFIXUTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  40.54
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  N-甲基邻苯二甲酰亚胺 、 以 水 、 丙酮 为溶剂， 反应 2.0h， 以36%的产率得到3-(4-fluorobenzyl)-3-hydroxy-2-methylisoindolin-1-one
  参考文献：
  名称：

  Photodecarboxylative benzylations of phthalimides

  摘要：

  Photoadditions of phenylacetates to phthalimides give the corresponding benzylated hydroxyphthalimidines in moderate to high yields of 29-90%. With 2-phenylpropanoate, photoaddition affords a diastereoisomeric mixture in a de of 24% in favour of the like-diastereoisomer. L-3-Phenyl lactate and 2-oxo-3-phenylpropanoate both furnish the benzylated product through subsequent loss of formaldehyde and decarbonylation, respectively. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.08.115

文献信息

• Intermolecular photodecarboxylation of electron-deficient substrates by phthalimides in water: efficiency, selectivity and online monitoring
  作者：Axel G. Griesbeck、Nestor Nazarov、Jörg M. Neudörfl、Maria Heffen

  DOI：10.1039/c2gc36089f

  日期：——

  The intermolecular photodecarboxylation of arylacetic acids 3–5 in water by use of stoichiometric amounts of N-alkylated phthalimides 1a,b was investigated by NMR and online pH- and CO2-release sensing. Decreasing the electron donor capability of the arylacetic acids by 4-fluoro and trifluoromethyl substitution alters the efficiency of the photodecarboxylation and selectivity of the secondary reaction. A remarkable switch in reaction channel (A to B) was observed for perfluoropropionic acid.

  通过核磁共振以及在线 pH 和 CO2 释放传感，研究了使用等量的 N-烷基邻苯二甲酰亚胺 1a,b 在水中对芳基乙酸 3-5 进行分子间光脱羧反应的情况。通过 4 氟和三氟甲基取代降低芳基乙酸的电子供体能力，改变了光脱羧反应的效率和二级反应的选择性。全氟丙酸的反应通道（A 到 B）发生了明显的变化。