(R)-3-(1-tert-Butyldiphenylsilyloxyhept-6-en-4-yl)-2,3-dihydrooxazol-2-one | 176858-53-0

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (R)-3-(1-tert-Butyldiphenylsilyloxyhept-6-en-4-yl)-2,3-dihydrooxazol-2-one
• 英文别名: 3-[(4R)-7-[tert-butyl(diphenyl)silyl]oxyhept-1-en-4-yl]-1,3-oxazol-2-one
• CAS: 176858-53-0
• 化学式: C₂₆H₃₃NO₃Si
• 分子量: 435.638
• InChiKey: HCDFNOMLFVBALA-QFIPXVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.92
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-3-(1-tert-Butyldiphenylsilyloxyhept-6-en-4-yl)-2,3-dihydrooxazol-2-one 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以77%的产率得到(R)-3-(1-Hydroxyhept-6-en-4-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
• 作为产物：
  描述：

  3-[(4S)-2,2-二甲基-1,3-二氧戊烷-4-基]-丙醇 在 吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 18-冠醚-6 、 偶氮二甲酸二异丙酯 、 三氟化硼乙醚 、 sodium hydride 、 对甲苯磺酸 、 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 为溶剂， 反应 77.17h， 生成 (R)-3-(1-tert-Butyldiphenylsilyloxyhept-6-en-4-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

文献信息

• Diastereoselective synthesis of 2,5-disubstituted 3-hydroxypyrrolidine and 2,6-disubstituted 3-hydroxypiperidine derivatives by radical cyclisation; synthesis of (+)-bulgecinine and (–)-desoxoprosopinine
  作者：Yoko Yuasa、Jun Ando、Shiroshi Shibuya

  DOI：10.1039/p19960000793

  日期：——

  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.