(R)-3-(4-isopropyl-3-methoxyphenyl)-3-methylcyclohexane-1-one

• 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: (R)-3-(4-isopropyl-3-methoxyphenyl)-3-methylcyclohexane-1-one
• 英文别名: (3R)-3-(3-methoxy-4-propan-2-ylphenyl)-3-methylcyclohexan-1-one
• 化学式: C₁₇H₂₄O₂
• 分子量: 260.376
• InChiKey: UFYWCVFXGXDQFK-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 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：

  (R)-3-(4-isopropyl-3-methoxyphenyl)-3-methylcyclohexane-1-one 在 四氯化钛 、 magnesium 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 (4aS)-6-methoxy-1,4a-dimethyl-7-propan-2-yl-3,4-dihydro-2H-fluoren-1-ol
  参考文献：
  名称：

  Catalytic asymmetric formal total synthesis of (+)-dichroanone and (+)-taiwaniaquinone H

  摘要：

  Catalytic asymmetric formal total synthesis of (+)-dichroanone and (+)-taiwaniaquinone H has been achieved. Key step involved construction of all-carbon quaternary carbon by palladium-catalyzed conjugate addition of arylboronic acid to 3-methyl cyclohexenone. Furthermore, a new approach to build [6-5-6] tricyclic backbone via formyl introduction and subsequent aldol-type condensation was also explored. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.08.110
• 作为产物：
  描述：

  2-溴邻苯二酚 在 4-二甲氨基吡啶 、 正丁基锂 、 (1,5-cyclooctadiene)(methoxy)iridium(I) dimer 、 ammonium hexafluorophosphate 、 palladium(II) trifluoroacetate 、 3,4,7,8-四甲基-1,10-菲罗啉 、 硫酸 、 palladium 10% on activated carbon 、 水 、 氢气 、 palladium diacetate 、 potassium carbonate 、 三乙胺 、 三苯基膦 、 (S)-4-叔丁基-2-(2-氮苯基)恶唑啉 、 乙硫醇 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 正己烷 、 二氯甲烷 、 水 、 乙酸乙酯 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 170.0 ℃ 、101.33 kPa 条件下， 反应 182.33h， 生成 (R)-3-(4-isopropyl-3-methoxyphenyl)-3-methylcyclohexane-1-one
  参考文献：
  名称：

  A Catalytic, Enantioselective Formal Synthesis of (+)-Dichroanone and (+)-Taiwaniaquinone H

  摘要：

  A catalytic, enantioselective formal synthesis of (+)-dichroanone and (+)-taiwaniaquinone H is reported. The all-carbon quaternary stereocenter was constructed by asymmetric conjugate addition catalyzed by a palladium(II) (S)-tert-butylpyridinooxazoline complex. The unexpected formation of a [3.2.1] bicyclic intermediate required the identification of a new route. Analysis of the Hammett constants for para-substituted arenes enabled the rational design of a highly enantioselective conjugate addition substrate that led to the completion of the formal synthesis.

  DOI：

  10.1021/ol5031537

文献信息

• A Catalytic, Enantioselective Formal Synthesis of (+)-Dichroanone and (+)-Taiwaniaquinone H
  作者：Samantha E. Shockley、Jeffrey C. Holder、Brian M. Stoltz

  DOI：10.1021/ol5031537

  日期：2014.12.19

  A catalytic, enantioselective formal synthesis of (+)-dichroanone and (+)-taiwaniaquinone H is reported. The all-carbon quaternary stereocenter was constructed by asymmetric conjugate addition catalyzed by a palladium(II) (S)-tert-butylpyridinooxazoline complex. The unexpected formation of a [3.2.1] bicyclic intermediate required the identification of a new route. Analysis of the Hammett constants for para-substituted arenes enabled the rational design of a highly enantioselective conjugate addition substrate that led to the completion of the formal synthesis.
• Catalytic asymmetric formal total synthesis of (+)-dichroanone and (+)-taiwaniaquinone H
  作者：Liang-Qun Li、Ming-Ming Li、Dong Chen、Hao-Miao Liu、Hui-chun Geng、Jun Lin、Hong-Bo Qin

  DOI：10.1016/j.tetlet.2014.08.110

  日期：2014.10

  Catalytic asymmetric formal total synthesis of (+)-dichroanone and (+)-taiwaniaquinone H has been achieved. Key step involved construction of all-carbon quaternary carbon by palladium-catalyzed conjugate addition of arylboronic acid to 3-methyl cyclohexenone. Furthermore, a new approach to build [6-5-6] tricyclic backbone via formyl introduction and subsequent aldol-type condensation was also explored. (C) 2014 Elsevier Ltd. All rights reserved.