(+)-isoampullicin

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (+)-isoampullicin
• 英文别名: isoampullicin；(5Z)-3-methyl-5-[[(1R,3S,6R,9R)-6-methyl-8-oxo-7-oxatricyclo[4.3.0.03,9]nonan-9-yl]methylidene]pyrrol-2-one
• 化学式: C₁₅H₁₇NO₃
• 分子量: 259.305
• InChiKey: GQFPCYNDHKNZCF-KOZHPBHNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-甲基-2-吡咯烷酮 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 四丁基氟化铵 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 四氢呋喃 、 四氯化碳 、 乙醚 、 甲苯 为溶剂， 反应 8.0h， 生成 (+)-isoampullicin
  参考文献：
  名称：

  Total synthesis of (−)-ampullicin and (+)-isoampullicin two growth regulators from Ampulliferina Sp. No. 27

  摘要：

  The growth regulators (-)-Ampullicin (1) and (+)-isoampullicin (2) have been synthesized utilizing carbaldehyde (25) as the chiral source and N-tertbutoxycarbonyl-3-methyl-2-(trimethylsiloxy)pyrrole (33) as the five-carbon homologative reagent. The synthesis of (1) and (2) is discussed in the context of retrosynthetic analysis. Carbaldehyde (25), has been prepared from both enantiomers of carvone, either (7) or (9), by application of a 15-step sequence with 4.7% and 5.4% overall yields respectively.

  DOI：

  10.1016/0040-4039(95)01625-r

文献信息

• Stereoselective preparation of (5E)- and (5Z)-5-benzylidene-3-methyl-3-pyrrolin-2-ones. Application to the synthesis of ampullicine and isoampullicine
  作者：Rosario Rico、Francisco Bermejo

  DOI：10.1016/0040-4039(96)01232-4

  日期：1996.8

  The application of N-Boc-5-phosphoranylidene- and N-Boc-5-diethylphosphonate-3-methyl-3-pyrrolin-2-ones to the stereoselective synthesis of (5E)- and (5Z)-3-methyl-5-benzylidene-3-pyrrolin-2-ones is examined. The stereoselective synthesis of the growth regulators Ampullicin and Isoampullicin by using both Wittig intermediates has also been achieved.

  N-Boc-5-膦基亚烷基-和N-Boc-5-二乙基膦酸酯-3-甲基-3-吡咯啉-2-酮在（5E）-和（5Z）-3-甲基-5的立体选择性合成中的应用检查了-亚苄基-3-吡咯啉-2-酮。还已经通过使用两种Wittig中间体实现了生长调节剂Ampullicin和Isoampullicin的立体选择性合成。
• Total synthesis of (−)-ampullicin and (+)-isoampullicin two growth regulators from Ampulliferina Sp. No. 27
  作者：Rosario Rico、Francisco Bermejo

  DOI：10.1016/0040-4039(95)01625-r

  日期：1995.10

  The growth regulators (-)-Ampullicin (1) and (+)-isoampullicin (2) have been synthesized utilizing carbaldehyde (25) as the chiral source and N-tertbutoxycarbonyl-3-methyl-2-(trimethylsiloxy)pyrrole (33) as the five-carbon homologative reagent. The synthesis of (1) and (2) is discussed in the context of retrosynthetic analysis. Carbaldehyde (25), has been prepared from both enantiomers of carvone, either (7) or (9), by application of a 15-step sequence with 4.7% and 5.4% overall yields respectively.