N-[(2S)-4-methyl-1-oxopentan-2-yl]pyridine-2-carboxamide | 290816-74-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N-[(2S)-4-methyl-1-oxopentan-2-yl]pyridine-2-carboxamide
• CAS: 290816-74-9
• 化学式: C₁₂H₁₆N₂O₂
• 分子量: 220.271
• InChiKey: YAKYMBXTCTXSAL-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  59.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-[(2S)-4-methyl-1-oxopentan-2-yl]pyridine-2-carboxamide 在 六氯乙烷 、 三乙胺 、 三苯基膦 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以76%的产率得到2-(4-Isobutyloxazol-2-yl)pyridine
  参考文献：
  名称：

  A Practical Approach to the Synthesis of 2,4-Disubstituted Oxazoles from Amino Acids

  摘要：

  [GRAPHICS]A new sequence for the synthesis of various 2,4-disubstituted oxazoles from alpha-amino acids is reported. The method is shown to be general and incorporates the reagent combination, triphenylphosphine/hexachloroethane, for cyclodehydration of intermediate alpha-acylamino aldehydes. Implementation of this reagent system for the conversion of alpha-acylamino ketones to oxazoles is briefly investigated.

  DOI：

  10.1021/ol020092s
• 作为产物：
  描述：

  N-(叔丁氧基羰基)-L-亮氨酸-N′-甲氧基-N′-甲酰胺 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 N-[(2S)-4-methyl-1-oxopentan-2-yl]pyridine-2-carboxamide
  参考文献：
  名称：

  A Practical Approach to the Synthesis of 2,4-Disubstituted Oxazoles from Amino Acids

  摘要：

  [GRAPHICS]A new sequence for the synthesis of various 2,4-disubstituted oxazoles from alpha-amino acids is reported. The method is shown to be general and incorporates the reagent combination, triphenylphosphine/hexachloroethane, for cyclodehydration of intermediate alpha-acylamino aldehydes. Implementation of this reagent system for the conversion of alpha-acylamino ketones to oxazoles is briefly investigated.

  DOI：

  10.1021/ol020092s

文献信息

• Protease inhibitors
  申请人：SmithKline Beecham Corporation

  公开号：US20020065230A1

  公开（公告）日：2002-05-30

  The present invention provides bis-aminomethylcarbonyl compounds that are inhibitors of cysteine and serine proteases. The compounds are particularly useful for treating diseases in which excess cysteine protease activity has been implicated, including osteoporosis, periodontitis and arthritis.

  本发明提供了一种双氨甲基羰基化合物，它们是半胱氨酸和丝氨酸蛋白酶的抑制剂。这些化合物特别适用于治疗过多半胱氨酸蛋白酶活性已被指认的疾病，包括骨质疏松症、牙周炎和关节炎。
• PROTEASE INHIBITORS
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：EP0983228A1

  公开（公告）日：2000-03-08
• EP0983228A4
  申请人：——

  公开号：EP0983228A4

  公开（公告）日：2002-08-07
• [EN] PROTEASE INHIBITORS<br/>[FR] INHIBITEURS DE PROTEASES
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：WO1998050342A1

  公开（公告）日：1998-11-12

  (EN) The present invention provides bis-aminomethylcarbonyl compounds that are inhibitors of cysteine and serine proteases. The compounds are particularly useful for treating diseases in which excess cysteine protease activity has been implicated, including osteoporosis, periodontitis and arthritis.(FR) L'invention porte sur des composés de bis-aminométhylcarbonyl inhibiteurs des protéases de la cystéine et de la sérine. Lesdits composés s'avèrent particulièrement utiles pour traiter les maladies impliquant un excès d'activité de la protéase de la cystéine, dont l'ostéoporose, la périodontite ou l'arthrose.
• A Practical Approach to the Synthesis of 2,4-Disubstituted Oxazoles from Amino Acids
  作者：Tina Morwick、Matt Hrapchak、Molly DeTuri、Scot Campbell

  DOI：10.1021/ol020092s

  日期：2002.8.1

  [GRAPHICS]A new sequence for the synthesis of various 2,4-disubstituted oxazoles from alpha-amino acids is reported. The method is shown to be general and incorporates the reagent combination, triphenylphosphine/hexachloroethane, for cyclodehydration of intermediate alpha-acylamino aldehydes. Implementation of this reagent system for the conversion of alpha-acylamino ketones to oxazoles is briefly investigated.