(3R,7aS)-3-phenyl-7a-(9-phenylnonyl)-2,3,6,7-tetrahydropyrrolo[2,1-b][1,3]oxazol-5-one | 177706-81-9

• 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: (3R,7aS)-3-phenyl-7a-(9-phenylnonyl)-2,3,6,7-tetrahydropyrrolo[2,1-b][1,3]oxazol-5-one
• CAS: 177706-81-9
• 化学式: C₂₇H₃₅NO₂
• 分子量: 405.58
• InChiKey: LNVXAOLCECXYQE-BDYUSTAISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3R,7aS)-3-phenyl-7a-(9-phenylnonyl)-2,3,6,7-tetrahydropyrrolo[2,1-b][1,3]oxazol-5-one 在 palladium on activated charcoal lithium aluminium tetrahydride 、 三氯化铝 、 氢气 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， -78.0~20.0 ℃ 、399.99 kPa 条件下， 反应 49.0h， 生成 (R)-2-(9-phenylnonyl)pyrrolidine
  参考文献：
  名称：

  Enantioselective Total Synthesis of Irniine and Bgugaine, Bioactive 2-Alkylpyrrolidine Alkaloids

  摘要：

  An asymmetric total synthesis of the 2-(R)-alkylpyrrolidines, (-)-irniine (1a) and (-)-bgugaine (1b), toxic and antibiotic components of the tubers of Arisarum vulgare, and (+)-(S)-irniine (1c), was carried out by condensation of the corresponding 4-oxoalkanoic acid (9) with chiral phenylglycinol. Acids (9) were prepared from a hetero-organocuprate (I) complex, generated by reaction of methylcopper (I) with alkylmagnesium bromides and methyl chlorocarbonyl-propionate. Alkaloids (1a, 1b and 1c) displayed anti Gram(+) bacterial (MIC 12.5 - 50 mu g/ml) and antifungal (MIC 6.25 - 50 mu g/ml) activities.

  DOI：

  10.3987/com-95-7293
• 作为产物：
  描述：

  6-碘己酸 在 氢氧化钾 、 copper(l) iodide 、 lithium aluminium tetrahydride 、 硫酸 、 氢溴酸 、 甲基锂 、 magnesium 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 水 、 甲苯 为溶剂， 反应 60.0h， 生成 (3R,7aS)-3-phenyl-7a-(9-phenylnonyl)-2,3,6,7-tetrahydropyrrolo[2,1-b][1,3]oxazol-5-one
  参考文献：
  名称：

  Enantioselective Total Synthesis of Irniine and Bgugaine, Bioactive 2-Alkylpyrrolidine Alkaloids

  摘要：

  An asymmetric total synthesis of the 2-(R)-alkylpyrrolidines, (-)-irniine (1a) and (-)-bgugaine (1b), toxic and antibiotic components of the tubers of Arisarum vulgare, and (+)-(S)-irniine (1c), was carried out by condensation of the corresponding 4-oxoalkanoic acid (9) with chiral phenylglycinol. Acids (9) were prepared from a hetero-organocuprate (I) complex, generated by reaction of methylcopper (I) with alkylmagnesium bromides and methyl chlorocarbonyl-propionate. Alkaloids (1a, 1b and 1c) displayed anti Gram(+) bacterial (MIC 12.5 - 50 mu g/ml) and antifungal (MIC 6.25 - 50 mu g/ml) activities.

  DOI：

  10.3987/com-95-7293

文献信息

• Enantioselective Total Synthesis of Irniine and Bgugaine, Bioactive 2-Alkylpyrrolidine Alkaloids
  作者：Akino Jossang、Ahmed Melhaoui、Bernard Bodo

  DOI：10.3987/com-95-7293

  日期：——

  An asymmetric total synthesis of the 2-(R)-alkylpyrrolidines, (-)-irniine (1a) and (-)-bgugaine (1b), toxic and antibiotic components of the tubers of Arisarum vulgare, and (+)-(S)-irniine (1c), was carried out by condensation of the corresponding 4-oxoalkanoic acid (9) with chiral phenylglycinol. Acids (9) were prepared from a hetero-organocuprate (I) complex, generated by reaction of methylcopper (I) with alkylmagnesium bromides and methyl chlorocarbonyl-propionate. Alkaloids (1a, 1b and 1c) displayed anti Gram(+) bacterial (MIC 12.5 - 50 mu g/ml) and antifungal (MIC 6.25 - 50 mu g/ml) activities.