(5R,8R,8aS)-8-Benzyloxy-5-(3'-oxopropyl)oxazolo<3,4-a>piperidin-3-one | 169304-57-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (5R,8R,8aS)-8-Benzyloxy-5-(3'-oxopropyl)oxazolo<3,4-a>piperidin-3-one
• 英文别名: 3-[(5R,8R,8aS)-3-oxo-8-phenylmethoxy-1,5,6,7,8,8a-hexahydro-[1,3]oxazolo[3,4-a]pyridin-5-yl]propanal
• CAS: 169304-57-8
• 化学式: C₁₇H₂₁NO₄
• 分子量: 303.358
• InChiKey: XTGMOKJNGSTZKL-HRCADAONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5R,8R,8aS)-8-Benzyloxy-5-(3'-oxopropyl)oxazolo<3,4-a>piperidin-3-one 在 palladium on activated charcoal 盐酸 、 正丁基锂 、 氢气 作用下， 以 甲醇 为溶剂， 反应 4.25h， 生成 (5S,8R,8aS)-5-Dodec-8-hydroxyoxazolo<3,4-a>piperidin-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：

  (S)-3-(1-Hydroxyoct-7-en-4-yl)-2,3-dihydrooxazol-2-one 在 草酰氯 、 偶氮二异丁腈 、 四丁基溴化铵 、 三正丁基氢锡 、 sodium hydride 、 臭氧 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 20.83h， 生成 (5R,8R,8aS)-8-Benzyloxy-5-(3'-oxopropyl)oxazolo<3,4-a>piperidin-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

文献信息

• Enantioselective Synthesis of (−)-desoxoprosopinine by radical cyclization
  作者：Yoko Yuasa、Jun Ando、Shiroshi Shibuya

  DOI：10.1016/0957-4166(95)00189-v

  日期：1995.7

  Reaction of the aldehyde 12 with tributyltin hydride in the presence of AIBN gave a mixture of 13 as a 2:1 mixture of 8 beta-ol. and 8 alpha-ol. Conversion of 14, derived from 13, to (-)-desoxoprosopinine 3 was successfully achieved.