(1S,2R,5R)-5-methyl-8-methylidene-2-propan-2-ylbicyclo[3.2.1]octan-6-one | 194790-42-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2R,5R)-5-methyl-8-methylidene-2-propan-2-ylbicyclo[3.2.1]octan-6-one
• CAS: 194790-42-6
• 化学式: C₁₃H₂₀O
• 分子量: 192.301
• InChiKey: GGXDWDAWLITEOB-NQBHXWOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1S,2R,5R)-5-methyl-8-methylidene-2-propan-2-ylbicyclo[3.2.1]octan-6-one 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 生成 (1R,2R,5R,6R,7R)-7-((S)-1-Hydroxy-5-methyl-hex-4-enyl)-2-isopropyl-5-methyl-8-methylene-6-trimethylsilanylmethyl-bicyclo[3.2.1]octan-6-ol
  参考文献：
  名称：

  Synthesis of (+)-sorokinianin

  摘要：

  Sorokinianin (1), an inhibitor of barley germination, was synthesized in optically active form employing d-carvone as the only chiral source. The key steps are stereoselective intra- and intermolecular aldol reactions to construct the bicyclo[3.2.1]octane system and to introduce the lactone moiety, respectively. Our synthetic 1 showed dextrorotation and the absolute configuration of natural 1 was confirmed to be 1R,4R,5S,6R,8S,13S,2'R. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01337-3
• 作为产物：
  描述：

  dihydrocarvone 在 咪唑 、 jones' reagent 、 二甲基硫 、 氢氟酸 、 sodium methylate 、 碳酸氢钠 、 臭氧 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 六甲基磷酰三胺 、 乙二醇二甲醚 、 丙酮 、 乙腈 为溶剂， 反应 2.0h， 生成 (1S,2R,5R)-5-methyl-8-methylidene-2-propan-2-ylbicyclo[3.2.1]octan-6-one
  参考文献：
  名称：

  Synthesis of (+)-sorokinianin

  摘要：

  Sorokinianin (1), an inhibitor of barley germination, was synthesized in optically active form employing d-carvone as the only chiral source. The key steps are stereoselective intra- and intermolecular aldol reactions to construct the bicyclo[3.2.1]octane system and to introduce the lactone moiety, respectively. Our synthetic 1 showed dextrorotation and the absolute configuration of natural 1 was confirmed to be 1R,4R,5S,6R,8S,13S,2'R. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01337-3

文献信息

• Synthesis of (+)-sorokinianin
  作者：Hidenori Watanabe、Takahiro Onoda、Takeshi Kitahara、Kenji Mori

  DOI：10.1016/s0040-4039(97)01337-3

  日期：1997.8

  Sorokinianin (1), an inhibitor of barley germination, was synthesized in optically active form employing d-carvone as the only chiral source. The key steps are stereoselective intra- and intermolecular aldol reactions to construct the bicyclo[3.2.1]octane system and to introduce the lactone moiety, respectively. Our synthetic 1 showed dextrorotation and the absolute configuration of natural 1 was confirmed to be 1R,4R,5S,6R,8S,13S,2'R. (C) 1997 Elsevier Science Ltd.