3-hydroxy-3-[(3-methylphenyl)methyl]-2H-isoindol-1-one | 1246376-46-4

• 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-hydroxy-3-[(3-methylphenyl)methyl]-2H-isoindol-1-one
• CAS: 1246376-46-4
• 化学式: C₁₆H₁₅NO₂
• 分子量: 253.301
• InChiKey: NCKLKKWGXUWRSH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-hydroxy-3-[(3-methylphenyl)methyl]-2H-isoindol-1-one 在 硫酸 作用下， 以 二氯甲烷 为溶剂， 以82%的产率得到
  参考文献：
  名称：

  Photodecarboxylative benzylations of phthalimide in pH 7 buffer: a simple access to 3-arylmethyleneisoindolin-1-ones

  摘要：

  Photoadditions of phenylacetates to phthalimide in pH 7 buffer solution give the corresponding benzylated-hydroxyphthalimidines in moderate to high yields of up to 94%. In a micro-structured reactor, higher conversions and purities are achieved. With branched phenylacetates, photoaddition affords diastereoisomeric mixtures with low to moderate de values. Subsequent acid-catalyzed dehydration furnishes the corresponding 3-arylmethyleneisoindolin-1-ones in good to excellent yields and with high E-selectivities. Irradiation of the parent 3-phenylmethyleneisoindolin-1-one under oxidative conditions only leads to cis/trans-isomerization. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.07.017
• 作为产物：
  描述：

  邻苯二甲酸亚胺 、 potassium 2-(m-tolyl)acetate 以 丙酮 为溶剂， 反应 3.0h， 以92%的产率得到3-hydroxy-3-[(3-methylphenyl)methyl]-2H-isoindol-1-one
  参考文献：
  名称：

  Photodecarboxylative benzylations of phthalimide in pH 7 buffer: a simple access to 3-arylmethyleneisoindolin-1-ones

  摘要：

  Photoadditions of phenylacetates to phthalimide in pH 7 buffer solution give the corresponding benzylated-hydroxyphthalimidines in moderate to high yields of up to 94%. In a micro-structured reactor, higher conversions and purities are achieved. With branched phenylacetates, photoaddition affords diastereoisomeric mixtures with low to moderate de values. Subsequent acid-catalyzed dehydration furnishes the corresponding 3-arylmethyleneisoindolin-1-ones in good to excellent yields and with high E-selectivities. Irradiation of the parent 3-phenylmethyleneisoindolin-1-one under oxidative conditions only leads to cis/trans-isomerization. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.07.017

文献信息

• Asymmetric hydrogenolysis of racemic tertiary alcohols, 3-substituted 3-hydroxyisoindolin-1-ones
  作者：Mu-Wang Chen、Qing-An Chen、Ying Duan、Zhi-Shi Ye、Yong-Gui Zhou

  DOI：10.1039/c2cc16832d

  日期：——

  Asymmetric hydrogenolysis of racemic tertiary alcohols, 3-substituted 3-hydroxyisoindolin-1-ones, was developed using chiral phosphoric acid as catalyst and a Hantzsch ester as the hydrogen source with up to 95% ee. The reaction process of this asymmetric transfer hydrogenation may occur directly through the acyliminium ion intermediate.

  使用手性磷酸作为催化剂和 Hantzsch 酯作为氢源开发了外消旋叔醇（3-取代的 3-羟基异吲哚啉-1-酮）的不对称氢解，其 ee 高达 95%。这种不对称转移氢化的反应过程可以直接通过酰亚胺离子中间体发生。
• Photodecarboxylative benzylations of phthalimide in pH 7 buffer: a simple access to 3-arylmethyleneisoindolin-1-ones
  作者：Vincent Belluau、Pierre Noeureuil、Elfrun Ratzke、Aleksei Skvortsov、Sonia Gallagher、Cherri Ann Motti、Michael Oelgemöller

  DOI：10.1016/j.tetlet.2010.07.017

  日期：2010.9

  Photoadditions of phenylacetates to phthalimide in pH 7 buffer solution give the corresponding benzylated-hydroxyphthalimidines in moderate to high yields of up to 94%. In a micro-structured reactor, higher conversions and purities are achieved. With branched phenylacetates, photoaddition affords diastereoisomeric mixtures with low to moderate de values. Subsequent acid-catalyzed dehydration furnishes the corresponding 3-arylmethyleneisoindolin-1-ones in good to excellent yields and with high E-selectivities. Irradiation of the parent 3-phenylmethyleneisoindolin-1-one under oxidative conditions only leads to cis/trans-isomerization. (C) 2010 Elsevier Ltd. All rights reserved.