(1R,4R,5R)-4-([1,2,4]triazolo[4,3-a]pyrimidin-3-yl)-1,8,8-trimethyl-2-oxabicyclo[3.2.1]octan-3-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三唑并嘧啶类
• 英文名称: (1R,4R,5R)-4-([1,2,4]triazolo[4,3-a]pyrimidin-3-yl)-1,8,8-trimethyl-2-oxabicyclo[3.2.1]octan-3-one
• 英文别名: (1R,4R,5R)-1,8,8-trimethyl-4-([1,2,4]triazolo[4,3-a]pyrimidin-3-yl)-2-oxabicyclo[3.2.1]octan-3-one
• 化学式: C₁₅H₁₈N₄O₂
• 分子量: 286.334
• InChiKey: SSPJZKJURYUHON-IQMDTDKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  69.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-肼基嘧啶 、 (1R,4E,5S)-4-[(dimethylamino)methylidene]-1,8,8-trimethyl-2-oxabicyclo[3.2.1]octan-3-one 在 硫酸 、 lead(IV) acetate 作用下， 以 甲醇 为溶剂， 反应 25.0h， 以54%的产率得到(1R,4E,5S)-4-{[(E)-(pyrimidin-2-yl)diazenyl]methylidene}-1,8,8-trimethyl-2-oxabicyclo[3.2.1]octan-3-one
  参考文献：
  名称：

  Synthesis of (1R,4E,5S)-4-{[(E)-(azinyl)diazenyl]methylidene}-1,8,8-trimethyl-2-oxabicyclo[3.2.1]octan-3-ones and (1R,4R,5R)-4-([1,2,4]triazolo[4,3-x]azin-3-yl)-1,8,8-trimethyl-2-oxabicyclo[3.2.1]octan-3-ones

  摘要：

  4-[(Heteroaryldiazenyl)methylidene] and 4-([1,2,4]triazolo[4,3-x]azin-3-yl) substituted (1R,5R)-4-1,8,8-trimethyl-2-oxabicyclo[3.2.1]octan-3-ones 6/6' and 7/7' were obtained in a one-pot transformation of the enamino lactone 2 with hydrazinoazines 3a-g followed by oxidation of the intermediate mixture of isomeric enehydrazines 4/4' and hydrazones 5/5' with lead tetraacetate. The oxidation selectivity was dependent on the ratio of isomeric intermediates 4/4' and 5/5'. Treatment of 7b with lead tetraacetate led to alpha-acetoxylated compound 11, while bromination of 9b afforded a 1:1 mixture of alpha-bromination products 12 and 12% which were separated by medium pressure liquid chromatography (M PLC). The structures of intermediates and products were confirmed by NMR and X-ray diffraction. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.07.032

文献信息

• Synthesis of (1R,4E,5S)-4-{[(E)-(azinyl)diazenyl]methylidene}-1,8,8-trimethyl-2-oxabicyclo[3.2.1]octan-3-ones and (1R,4R,5R)-4-([1,2,4]triazolo[4,3-x]azin-3-yl)-1,8,8-trimethyl-2-oxabicyclo[3.2.1]octan-3-ones
  作者：Uroš Grošelj、David Bevk、Renata Jakše、Anton Meden、Branko Stanovnik、Jurij Svete

  DOI：10.1016/j.tetasy.2005.07.032

  日期：2005.9

  4-[(Heteroaryldiazenyl)methylidene] and 4-([1,2,4]triazolo[4,3-x]azin-3-yl) substituted (1R,5R)-4-1,8,8-trimethyl-2-oxabicyclo[3.2.1]octan-3-ones 6/6' and 7/7' were obtained in a one-pot transformation of the enamino lactone 2 with hydrazinoazines 3a-g followed by oxidation of the intermediate mixture of isomeric enehydrazines 4/4' and hydrazones 5/5' with lead tetraacetate. The oxidation selectivity was dependent on the ratio of isomeric intermediates 4/4' and 5/5'. Treatment of 7b with lead tetraacetate led to alpha-acetoxylated compound 11, while bromination of 9b afforded a 1:1 mixture of alpha-bromination products 12 and 12% which were separated by medium pressure liquid chromatography (M PLC). The structures of intermediates and products were confirmed by NMR and X-ray diffraction. (c) 2005 Elsevier Ltd. All rights reserved.