3-(5-Oxopentan-2-yl)-2,3-dihydrooxazol-2-one | 176858-49-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(5-Oxopentan-2-yl)-2,3-dihydrooxazol-2-one
• 英文别名: 4-(2-Oxo-1,3-oxazol-3-yl)pentanal
• CAS: 176858-49-4
• 化学式: C₈H₁₁NO₃
• 分子量: 169.18
• InChiKey: WAHIEYGGXAAJOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(5-Oxopentan-2-yl)-2,3-dihydrooxazol-2-one 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 5.0h， 以84.7%的产率得到(5R,8aR)-8-hydroxy-5-methyl-1,5,6,7,8,8a-hexahydro-[1,3]oxazolo[3,4-a]pyridin-3-one
  参考文献：
  名称：

  Diastereoselective synthesis of 2,5-disubstituted 3-hydroxypyrrolidine and 2,6-disubstituted 3-hydroxypiperidine derivatives by radical cyclisation; synthesis of (+)-bulgecinine and (–)-desoxoprosopinine

  摘要：

  Cyclisation of the O-stannyl ketyl, generated from the aldehyde 17 by reaction with tributyltin hydride in the presence of AIBN, gives the 5-benzyloxymethyl-7-hydroxypyrrolooxazolidin as a diastereoisomeric mixture of 7 alpha-ol 18 and 7 beta-ol 19 (2: 1), with high diastereoselectivity with respect to the 5,7a positions, (+)-Bulgecinine 8 is enantioselectively synthesised by stereospecific reduction of the ketone 20, derived from compounds 18 and 19. In a similar way, cyclisation of compound 40 gives a 2: 1 mixture of compounds 41 and 42. Conversion of compound 41 into (-)-desoxoprosopinine 9 is successfully achieved.

  DOI：

  10.1039/p19960000793
• 作为产物：
  描述：

  5-羟基-2-戊酮 在 咪唑 、 sodium tetrahydroborate 、 草酰氯 、 偶氮二甲酸二异丙酯 、 四丁基氟化铵 、 二甲基亚砜 、 甲基磺酰氯 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 45.5h， 生成 3-(5-Oxopentan-2-yl)-2,3-dihydrooxazol-2-one
  参考文献：
  名称：

  Diastereoselective synthesis of 2,5-disubstituted 3-hydroxypyrrolidine and 2,6-disubstituted 3-hydroxypiperidine derivatives by radical cyclisation; synthesis of (+)-bulgecinine and (–)-desoxoprosopinine

  摘要：

  Cyclisation of the O-stannyl ketyl, generated from the aldehyde 17 by reaction with tributyltin hydride in the presence of AIBN, gives the 5-benzyloxymethyl-7-hydroxypyrrolooxazolidin as a diastereoisomeric mixture of 7 alpha-ol 18 and 7 beta-ol 19 (2: 1), with high diastereoselectivity with respect to the 5,7a positions, (+)-Bulgecinine 8 is enantioselectively synthesised by stereospecific reduction of the ketone 20, derived from compounds 18 and 19. In a similar way, cyclisation of compound 40 gives a 2: 1 mixture of compounds 41 and 42. Conversion of compound 41 into (-)-desoxoprosopinine 9 is successfully achieved.

  DOI：

  10.1039/p19960000793