(2S,3S)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-hydroxy-4-methyl-pentanal | 779337-11-0

• 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: (2S,3S)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-hydroxy-4-methyl-pentanal
• 英文别名: (2S,3S)-2-(1,3-dioxoisoindol-2-yl)-3-hydroxy-4-methylpentanal
• CAS: 779337-11-0
• 化学式: C₁₄H₁₅NO₄
• 分子量: 261.277
• InChiKey: XOHHHISOAYTBPG-NEPJUHHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  74.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3S)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-hydroxy-4-methyl-pentanal 在 sodium chlorite 、 肼 作用下， 生成 (2S,3S)-2-氨基-3-羟基-4-甲基-戊酸
  参考文献：
  名称：

  [EN] REACTIONS OF ENOLIZABLE A-AMINO ALDEHYDES OR KETONES TO FORM AMINE
  [FR] REACTIONS ASYMETRIQUES ORGANOCATALYTIQUES DIRECTES D'ALPHA-AMINO-ALDEHYDES OU -CETONES ENOLISABLES EN VUE DE LA FORMATION DE PRODUITS AMINES ENANTIOMERIQUEMENT ENRICHIS

  摘要：

  公开号：

  WO2006023720A3
• 作为产物：
  描述：

  N-烯丙基邻苯二甲酰亚胺 在 臭氧 、 L-脯氨酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 69.0h， 生成 (2S,3S)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-hydroxy-4-methyl-pentanal
  参考文献：
  名称：

  Direct Organocatalytic Asymmetric Aldol Reactions of α-Amino Aldehydes:  Expedient Syntheses of Highly Enantiomerically Enriched anti-β-Hydroxy-α-amino Acids

  摘要：

  A simple and efficient method for the synthesis of highly enantiomerically enriched beta-hydroxy-alpha-amino acid derivatives has been developed. Direct asymmetric aldol reactions of a glycine aldehyde (aminoacetaldehyde) derivative have been performed under organocatalysis using L-proline or (5)-5-pyrrolidine-2-yl-1H-tetrazole. The reactions afforded anti-beta-hydroxy-alpha-amino aldehydes in good yield with high diastereoselectivity (dr up to >100:1) and high enantioselectivity (up to >99.5% ee), which were easily transformed into beta-hydroxy-alpha-amino acid derivatives.

  DOI：

  10.1021/ol0485417

文献信息

• [EN] REACTIONS OF ENOLIZABLE A-AMINO ALDEHYDES OR KETONES TO FORM AMINE<br/>[FR] REACTIONS ASYMETRIQUES ORGANOCATALYTIQUES DIRECTES D'ALPHA-AMINO-ALDEHYDES OU -CETONES ENOLISABLES EN VUE DE LA FORMATION DE PRODUITS AMINES ENANTIOMERIQUEMENT ENRICHIS
  申请人：SCRIPPS RESEARCH INST

  公开号：WO2006023720A3

  公开（公告）日：2007-01-11
• Direct Organocatalytic Asymmetric Aldol Reactions of α-Amino Aldehydes:  Expedient Syntheses of Highly Enantiomerically Enriched <i>a</i><i>nti</i>-β-Hydroxy-α-amino Acids
  作者：Rajeswari Thayumanavan、Fujie Tanaka、Carlos F. Barbas

  DOI：10.1021/ol0485417

  日期：2004.9.1

  A simple and efficient method for the synthesis of highly enantiomerically enriched beta-hydroxy-alpha-amino acid derivatives has been developed. Direct asymmetric aldol reactions of a glycine aldehyde (aminoacetaldehyde) derivative have been performed under organocatalysis using L-proline or (5)-5-pyrrolidine-2-yl-1H-tetrazole. The reactions afforded anti-beta-hydroxy-alpha-amino aldehydes in good yield with high diastereoselectivity (dr up to >100:1) and high enantioselectivity (up to >99.5% ee), which were easily transformed into beta-hydroxy-alpha-amino acid derivatives.