(S)-7-Isopropyl-1,1,4a-trimethyl-2,3,4,4a-tetrahydro-1H-fluorene | 901132-04-5

• 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: (S)-7-Isopropyl-1,1,4a-trimethyl-2,3,4,4a-tetrahydro-1H-fluorene
• 英文别名: (4aR)-1,1,4a-trimethyl-7-propan-2-yl-3,4-dihydro-2H-fluorene
• CAS: 901132-04-5
• 化学式: C₁₉H₂₆
• 分子量: 254.415
• InChiKey: UGODASAFMLESKC-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (S)-7-Isopropyl-1,1,4a-trimethyl-2,3,4,4a-tetrahydro-1H-fluorene 在 硫酸 、 双氧水 、 四氯化钛 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 氯仿 、 水 为溶剂， 反应 22.0h， 生成 (4bR)-4b,8,8-trimethyl-2-propan-2-yl-6,7-dihydro-5H-fluorene-3,4-dione
  参考文献：
  名称：

  The Catalytic Enantioselective, Protecting Group-Free Total Synthesis of (+)-Dichroanone

  摘要：

  Herein we report the first enantioselective total synthesis of (+)-dichroanone, confirming the absolute configuration of the natural product. This protecting group-free route features the first application of our enantioselective Tsuji allylation in the context of a natural product total synthesis. Additionally, this 11-step preparation of the molecule from commercial material features a novel Kumada-aromatization strategy and a rapid sequence for the conversion of a phenol to a hydroxy-p-benzoquinone.

  DOI：

  10.1021/ja061853f
• 作为产物：
  描述：

  Trifluoro-methanesulfonic acid (S)-4b,8,8-trimethyl-4a,4b,5,6,7,8-hexahydro-4H-fluoren-2-yl ester 、 异丙烯基溴化镁 在 四(三苯基膦)钯 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 以170 mg的产率得到(S)-7-Isopropyl-1,1,4a-trimethyl-2,3,4,4a-tetrahydro-1H-fluorene
  参考文献：
  名称：

  The Catalytic Enantioselective, Protecting Group-Free Total Synthesis of (+)-Dichroanone

  摘要：

  Herein we report the first enantioselective total synthesis of (+)-dichroanone, confirming the absolute configuration of the natural product. This protecting group-free route features the first application of our enantioselective Tsuji allylation in the context of a natural product total synthesis. Additionally, this 11-step preparation of the molecule from commercial material features a novel Kumada-aromatization strategy and a rapid sequence for the conversion of a phenol to a hydroxy-p-benzoquinone.

  DOI：

  10.1021/ja061853f

文献信息

• The Catalytic Enantioselective, Protecting Group-Free Total Synthesis of (+)-Dichroanone
  作者：Ryan M. McFadden、Brian M. Stoltz

  DOI：10.1021/ja061853f

  日期：2006.6.1

  Herein we report the first enantioselective total synthesis of (+)-dichroanone, confirming the absolute configuration of the natural product. This protecting group-free route features the first application of our enantioselective Tsuji allylation in the context of a natural product total synthesis. Additionally, this 11-step preparation of the molecule from commercial material features a novel Kumada-aromatization strategy and a rapid sequence for the conversion of a phenol to a hydroxy-p-benzoquinone.