(S)-3-(1-tert-Butyldiphenylsilyloxyoct-7-en-4-yl)oxazolidine-2,4-dione | 169304-51-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (S)-3-(1-tert-Butyldiphenylsilyloxyoct-7-en-4-yl)oxazolidine-2,4-dione
• 英文别名: 3-[(4S)-1-[tert-butyl(diphenyl)silyl]oxyoct-7-en-4-yl]-1,3-oxazolidine-2,4-dione
• CAS: 169304-51-2
• 化学式: C₂₇H₃₅NO₄Si
• 分子量: 465.665
• InChiKey: SLOGJEXMRFQEBJ-QFIPXVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.66
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 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：

  (S)-3-(1-tert-Butyldiphenylsilyloxyoct-7-en-4-yl)oxazolidine-2,4-dione 在 吡啶 、 sodium tetrahydroborate 、 四丁基氟化铵 、 甲基磺酰氯 作用下， 以 四氢呋喃 为溶剂， 生成 (S)-3-(1-Hydroxyoct-7-en-4-yl)-2,3-dihydrooxazol-2-one
  参考文献：
  名称：

  Enantioselective Synthesis of (−)-desoxoprosopinine by radical cyclization

  摘要：

  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.

  DOI：

  10.1016/0957-4166(95)00189-v
• 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 、 copper(l) iodide 、 18-冠醚-6 、 偶氮二甲酸二异丙酯 、 sodium hydride 、 对甲苯磺酸 、 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 64.08h， 生成 (S)-3-(1-tert-Butyldiphenylsilyloxyoct-7-en-4-yl)oxazolidine-2,4-dione
  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.
• 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.