1-hydroxy-1,3-dimethyl-1H-isoindole 1-oxide | 219908-66-4

• 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: 1-hydroxy-1,3-dimethyl-1H-isoindole 1-oxide
• 英文别名: 1,3-Dimethyl-2-oxidoisoindol-2-ium-1-ol
• CAS: 219908-66-4
• 化学式: C₁₀H₁₁NO₂
• 分子量: 177.203
• InChiKey: DMNZPRQWNRPZSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  49
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-hydroxy-1,3-dimethyl-1H-isoindole 1-oxide 在 ammonium hydroxide 、 copper diacetate 、 air 、 苯肼 作用下， 以 二氯甲烷 为溶剂， 反应 13.0h， 生成 2-hydroxy-1,3-dimethyl-1,3-diphenylisoindoline
  参考文献：
  名称：

  Symmetrical Nitroxide Synthesis:  Meso versus d,l Diastereomer Formation

  摘要：

  The syntheses of Ct-symmetrical isoindoline nitroxide 2a and meso-isoindoline nitroxide 2b have been achieved by two different routes. The chiral Ct-symmetric nitroxide derives from the addition of a Grignard reagent from the least hindered face opposite the large phenyl group in nitrone intermediate 21, whereas the isoindoline 3b precursor to the meso nitroxide is formed by the addition of a Grignard reagent from the face opposite the large magnesium oxide group of the tight ion pair of iminium 19. The assignment of these structures is confirmed by preparation of several derivatives as well as by X-ray crystallography.

  DOI：

  10.1021/jo981614d
• 作为产物：
  描述：

  1,3-二甲基-1H-异吲哚啉 在 sodium tungstate 、 过氧化脲素 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以37%的产率得到1-hydroxy-1,3-dimethyl-1H-isoindole 1-oxide
  参考文献：
  名称：

  Symmetrical Nitroxide Synthesis:  Meso versus d,l Diastereomer Formation

  摘要：

  The syntheses of Ct-symmetrical isoindoline nitroxide 2a and meso-isoindoline nitroxide 2b have been achieved by two different routes. The chiral Ct-symmetric nitroxide derives from the addition of a Grignard reagent from the least hindered face opposite the large phenyl group in nitrone intermediate 21, whereas the isoindoline 3b precursor to the meso nitroxide is formed by the addition of a Grignard reagent from the face opposite the large magnesium oxide group of the tight ion pair of iminium 19. The assignment of these structures is confirmed by preparation of several derivatives as well as by X-ray crystallography.

  DOI：

  10.1021/jo981614d

文献信息

• Symmetrical Nitroxide Synthesis:  Meso versus <i>d</i>,<i>l</i> Diastereomer Formation
  作者：Rebecca Braslau、Vladimir Chaplinski、Patricia Goodson

  DOI：10.1021/jo981614d

  日期：1998.12.1

  The syntheses of Ct-symmetrical isoindoline nitroxide 2a and meso-isoindoline nitroxide 2b have been achieved by two different routes. The chiral Ct-symmetric nitroxide derives from the addition of a Grignard reagent from the least hindered face opposite the large phenyl group in nitrone intermediate 21, whereas the isoindoline 3b precursor to the meso nitroxide is formed by the addition of a Grignard reagent from the face opposite the large magnesium oxide group of the tight ion pair of iminium 19. The assignment of these structures is confirmed by preparation of several derivatives as well as by X-ray crystallography.