Isochroman-3-carbaldehyde | 256229-08-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: Isochroman-3-carbaldehyde
• 英文别名: 3,4-dihydro-1H-isochromene-3-carbaldehyde
• CAS: 256229-08-0
• 化学式: C₁₀H₁₀O₂
• 分子量: 162.188
• InChiKey: HCTIUMQUFGCSST-UHFFFAOYSA-N

物化性质

• 沸点：
  293.4±28.0 °C(Predicted)
• 密度：
  1.211±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  氢氰酸 、 Isochroman-3-carbaldehyde 在 (S)-oxynitrilase from Hevea brasiliensis 作用下， 以 异丙醚 为溶剂， 生成 Hydroxy-isochroman-3-yl-acetonitrile
  参考文献：
  名称：

  Selectivity of the (S)-oxynitrilase from Hevea brasiliensis towards α- and β-substituted aldehydes

  摘要：

  The performance of (S)-oxynitrilase from Hevea brasiliensis (HbHNL) has been investigated with several alpha- and beta-substituted alkyl or alkoxy aldehydes and the results have been compared to the data previously obtained with the (R)-specific enzyme from almonds (PaHNL). With both enzymes there was no chiral discrimination between the enantiomers of the racemic substrates, therefore this reaction cannot be used as a preparative method to achieve both the kinetic resolution of the starting racemic aldehyde and the production of diastereomerically pure (or enriched) cyanohydrins. Additionally, in comparison with the (R)-PaHNL the (S)-selective enzyme from Hevea gave products with higher de, but was more negatively effected by oxygenated substituents. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00187-4
• 作为产物：
  描述：

  3,4-二氢-1H-异苯并吡喃-3-醇 在 palladium on activated charcoal 氢气 、 N-甲基吡啶-4-羰甲醛苯磺酸盐 、 正丁胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.25h， 生成 Isochroman-3-carbaldehyde
  参考文献：
  名称：

  Almond oxynitrilase-catalyzed transformation of aldehydes is strongly influenced by naphthyl and alkoxy substituents

  摘要：

  Different alpha- and beta-substituted aldehydes have been submitted to the catalytic action of almond oxynitrilase (PaHNL), in order to explore the influence of a stereocenter already present in the substrate on the selectivity of this enzyme.(1) The results indicate that naphthyl and alkoxy substituents in the alpha- and also in the beta-position to the aldehyde group significantly influence the stereochemical outcome of the PaHNL-catalyzed transformation. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00427-9

文献信息

• Selectivity of the (S)-oxynitrilase from Hevea brasiliensis towards α- and β-substituted aldehydes
  作者：Gabriella Roda、Sergio Riva、Bruno Danieli、Herfried Griengl、Uwe Rinner、Michael Schmidt、Antonina Mackova Zabelinskaja

  DOI：10.1016/s0040-4020(02)00187-4

  日期：2002.4

  The performance of (S)-oxynitrilase from Hevea brasiliensis (HbHNL) has been investigated with several alpha- and beta-substituted alkyl or alkoxy aldehydes and the results have been compared to the data previously obtained with the (R)-specific enzyme from almonds (PaHNL). With both enzymes there was no chiral discrimination between the enantiomers of the racemic substrates, therefore this reaction cannot be used as a preparative method to achieve both the kinetic resolution of the starting racemic aldehyde and the production of diastereomerically pure (or enriched) cyanohydrins. Additionally, in comparison with the (R)-PaHNL the (S)-selective enzyme from Hevea gave products with higher de, but was more negatively effected by oxygenated substituents. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Almond oxynitrilase-catalyzed transformation of aldehydes is strongly influenced by naphthyl and alkoxy substituents
  作者：Gabriella Roda、Sergio Riva、Bruno Danieli

  DOI：10.1016/s0957-4166(99)00427-9

  日期：1999.10

  Different alpha- and beta-substituted aldehydes have been submitted to the catalytic action of almond oxynitrilase (PaHNL), in order to explore the influence of a stereocenter already present in the substrate on the selectivity of this enzyme.(1) The results indicate that naphthyl and alkoxy substituents in the alpha- and also in the beta-position to the aldehyde group significantly influence the stereochemical outcome of the PaHNL-catalyzed transformation. (C) 1999 Elsevier Science Ltd. All rights reserved.