(1R,4S,6R,7S)-7-allyl-1-methyl-9-oxatricyclo<4.3.0.0^4.7>nonan-8-one | 148679-91-8

• 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: (1R,4S,6R,7S)-7-allyl-1-methyl-9-oxatricyclo<4.3.0.0^4.7>nonan-8-one
• 英文别名: (1R,3S,6R,9S)-6-methyl-9-prop-2-enyl-7-oxatricyclo[4.3.0.03,9]nonan-8-one
• CAS: 148679-91-8
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: HDUILVRCXMSKCP-XPXLGCRWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,4S,6R,7S)-7-allyl-1-methyl-9-oxatricyclo<4.3.0.0^4.7>nonan-8-one 在 四丁基氟化铵 作用下， 生成 (-)-ampullicin
  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
• 作为产物：
  描述：

  (+)-(1R,5R)-5-Isopropenyl-2-methylcyclohex-2-enylacetic acid 在 吡啶 、 咪唑 、 六甲基磷酰三胺 、 N-溴代丁二酰亚胺(NBS) 、 二甲基硫 、 偶氮二异丁腈 、 N-[(2,4-二氯苯氧基)-甲氧基硫代膦酰]丙-2-胺 、 四丁基氟化铵 、 三正丁基氢锡 、 sodium methylate 、 碳酸氢钠 、 臭氧 、 间氯过氧苯甲酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 93.0h， 生成 (1R,4S,6R,7S)-7-allyl-1-methyl-9-oxatricyclo<4.3.0.0^4.7>nonan-8-one
  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

• Total synthesis of (+)-massarinolin B and (+)-4-epi-massarinolin B, fungal metabolites from Massarina tunicata
  作者：María Rodríguez López、Francisco A. Bermejo

  DOI：10.1016/j.tet.2006.06.011

  日期：2006.8

  tricyclic chiral aldehydes with (E)-β-iodomethacrylates (Nozaki–Hiyama–Kishi reaction) was successfully applied to the preparation of some valuable key intermediates of our synthetic strategy to the fungal metabolites (+)-massarinolin B, (+)-4-epi-massarinolin B and (+)-massarinolin C.

  Cr（II）和Ni（II）介导的几种三环手性醛与（E）-β-碘甲基丙烯酸酯的偶合反应（野崎-小山-岸史反应）已成功地用于制备我们合成策略的一些有价值的关键中间体（+）-massarinolin B，（+）-4- Epi -massarinolin B和（+）-massarinolin C的代谢产物。
• Synthesis of Mono- and Sesquiterpenoids; XXII.¹Synthesis of (+)-Pinthunamide, a Sesquiterpene Metabolite of a Fungus,<i>Ampulliferina</i>sp.
  作者：Kenji Mori、Yoshitaka Matsushima

  DOI：10.1055/s-1993-25873

  日期：——

  Pinthunamide (1), a sesquiterpene metabolite produced by a fungus Ampulliferina sp., was synthesized by starting from (1R,4S,6S)-6-hydroxy-1-methylbicyclo[2.2.2]octan-2-one (4), which could readily be prepared by yeast reduction of the corresponding ß-diketone 5.

  Pinthunamide (1)是一种倍半萜类代谢产物，由真菌Ampulliferina sp.产生，由(1R,4S,6S)-6-羟基-1-甲基双环[2.2.2]辛烷-2-酮(4)合成，而(4)可通过酵母还原相应的β-二酮5来制备。
• Mori, Kenji, Bulletin des Societes Chimiques Belges, 1992, vol. 101, # 5, p. 393 - 406
  作者：Mori, Kenji

  DOI：——

  日期：——
• 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.