(2S,3S)-3-cyclopentyl-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-hydroxy-propionaldehyde | 779337-15-4

• 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: (2S,3S)-3-cyclopentyl-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-hydroxy-propionaldehyde
• 英文别名: (2S,3S)-3-cyclopentyl-3-hydroxy-2-(1,3-dioxoisoindolin-2-yl)propanal；(2S,3S)-3-cyclopentyl-2-(1,3-dioxoisoindol-2-yl)-3-hydroxypropanal
• CAS: 779337-15-4
• 化学式: C₁₆H₁₇NO₄
• 分子量: 287.315
• InChiKey: MPUGDCRDJPLKDU-KGLIPLIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  苄氧基胺盐酸盐 、 (2S,3S)-3-cyclopentyl-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-hydroxy-propionaldehyde 生成 3-cyclopentyl-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-hydroxy-propionaldehyde O-benzyl-oxime
  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
• 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 N-甲基吡咯烷酮 、 甲醇 、 二氯甲烷 为溶剂， 反应 21.0h， 生成 (2S,3S)-3-cyclopentyl-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-hydroxy-propionaldehyde
  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

• Diaminoalkane Aspartic Protease Inhibitors
  申请人：Baldwin John J.

  公开号：US20090018103A1

  公开（公告）日：2009-01-15

  Diaminoalkanes of Formula I have now been found which are orally active and bind to aspartic proteases to inhibit their activity. They are useful in the treatment or amelioration of diseases associated with elevated levels of aspartic protease activity. The invention also relates to a method for the use of the compounds of Formula I in ameliorating or treating aspartic protease related disorders in a subject in need thereof comprising administering to said subject an effective amount of a compound of Formula I.

  公式I的Diaminoalkanes现已被发现，它们具有口服活性并结合到天冬氨酸蛋白酶以抑制其活性。它们在治疗或改善与天冬氨酸蛋白酶活性升高相关的疾病方面非常有用。本发明还涉及使用公式I化合物治疗或改善需要的天冬氨酸蛋白酶相关疾病的方法，包括向该受体施用公式I化合物的有效量。
• Diaminoalkane aspartic protease inhibitors
  申请人：Vitae Pharmaceuticals, Inc.

  公开号：US07754737B2

  公开（公告）日：2010-07-13

  Diaminoalkanes of Formula I have now been found which are orally active and bind to aspartic proteases to inhibit their activity. They are useful in the treatment or amelioration of diseases associated with elevated levels of aspartic protease activity. The invention also relates to a method for the use of the compounds of Formula I in ameliorating or treating aspartic protease related disorders in a subject in need thereof comprising administering to said subject an effective amount of a compound of Formula I.

  已经发现了具有公式I的二氨基烷，其口服活性并结合天冬氨酸蛋白酶以抑制其活性。它们在治疗或改善与天冬氨酸蛋白酶活性升高相关的疾病方面是有用的。本发明还涉及一种使用公式I的化合物改善或治疗需要该方案的主体中的天冬氨酸蛋白酶相关疾病的方法，包括向该主体施用公式I的化合物的有效量。
• DIAMINOALKANE ASPARTIC PROTEASE INHIBITORS
  申请人：Vitae Pharmaceuticals, Inc.

  公开号：EP1807078A1

  公开（公告）日：2007-07-18
• US7754737B2
  申请人：——

  公开号：US7754737B2

  公开（公告）日：2010-07-13
• US8455521B2
  申请人：——

  公开号：US8455521B2

  公开（公告）日：2013-06-04