3-piperonylidene-isoindolin-1-one | 30190-57-9

• 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-piperonylidene-isoindolin-1-one
• 英文别名: 3-Piperonyliden-isoindolin-1-on；(3E)-3-(1,3-benzodioxol-5-ylmethylidene)isoindol-1-one
• CAS: 30190-57-9
• 化学式: C₁₆H₁₁NO₃
• 分子量: 265.268
• InChiKey: UZNNEKFZHNVXKG-NTUHNPAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-piperonylidene-isoindolin-1-one 在 硫酸 作用下， 生成 3-benzo[1,3]dioxol-5-ylmethyl-1,3-dihydro-isoindole
  参考文献：
  名称：

  Shigehara, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1944, vol. 64, p. 9,14

  摘要：

  DOI：
• 作为产物：
  描述：

  在 硫酸 作用下， 以 二氯甲烷 为溶剂， 以70%的产率得到3-piperonylidene-isoindolin-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

• A Stereoselective Synthesis of (<i>Z</i>)-3-Aryl and Alkylmethylidene-1<i>H</i>-isoindolin-1-ones
  作者：Axel Couture、Marc Lamblin、Eric Deniau、Pierre Grandclaudon

  DOI：10.1055/s-2006-926413

  日期：2006.4

  A series of Z-configured (hetero)aryl and alkylmethylideneisoindolin-1-ones has been efficiently prepared by treatment of N-methoxycarbonylisoindolin-1-ones with a base and reaction with selected aldehydes. The parent N-acylated isoindolin-1-ones have been assembled by a Parham-type cyclization of N-(2-iodoarylmethyl)dicarbamates.

  通过用碱处理N-甲氧羰基异吲哚啉-1-酮并与选定的醛反应，可以有效地制备一系列Z型（杂）芳基和烷基亚甲基异吲哚啉-1-酮。母体N-酰基化异吲哚啉-1-酮是通过N-(2-碘芳基甲基)二氨基甲酸酯的帕勒姆型环化反应组装而成的。
• Shigehara, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1944, vol. 64, p. 9,14
  作者：Shigehara

  DOI：——

  日期：——
• 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.