(7aR)-7a-methyl-1,2,5,6,7,7a-hexahydro-4H-inden-4-one | 850195-80-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (7aR)-7a-methyl-1,2,5,6,7,7a-hexahydro-4H-inden-4-one
• 英文别名: (R)-7a-methyl-1,2,5,6,7,7a-hexahydroinden-4-one；1,2,5,6,7,7a-hexahydro-7a-methylinden-4-one；(7aR)-7a-methyl-2,5,6,7-tetrahydro-1H-inden-4-one
• CAS: 850195-80-1
• 化学式: C₁₀H₁₄O
• 分子量: 150.221
• InChiKey: WVFQWKPDQCQLSD-JTQLQIEISA-N

物化性质

• 沸点：
  249.6±7.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  (7aR)-7a-methyl-1,2,5,6,7,7a-hexahydro-4H-inden-4-one 在 正丁基锂 、 叔丁基锂 、 sodium methylate 、 臭氧 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 正戊烷 为溶剂， 反应 176.25h， 生成 2-methyl-1-[(3S,3aR,4R,7aR)-7a-methyloctahydrospiro[indene-4,2'-oxiran]-3-yl]propan-1-one
  参考文献：
  名称：

  Total syntheses of the sesquiterpenoids (+)-trans-dracunculifoliol and (+)-4-hydroxyoppositan-7-one

  摘要：

  Sesquiterpenoids (+)-trans-dracuncuflifoliol (1) and (+)-4-hydroxyoppositan-7-one (2) were prepared stereoselectively from enantiomerically pure (7aR)-7a-methyl-1,2,5,6,7,7a-hexahydro-4H-inden-4-one ((-)-6), whose synthesis was described herein. Conjugate addition of the organocopper (1) reagent 10 to (-)-6, followed by epimerization of the ring junction, generated 3 of the 4 contiguous chiral centers of both natural products. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.01.089
• 作为产物：
  描述：

  hexahydro-1,2,6,7,7a methyl-7a 4H-indenone-4 (ou methyl-7a Δ^3(3a)-hydrindenone-4) 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 1.0h， 生成 (7aR)-7a-methyl-1,2,5,6,7,7a-hexahydro-4H-inden-4-one
  参考文献：
  名称：

  Total syntheses of the sesquiterpenoids (+)-trans-dracunculifoliol and (+)-4-hydroxyoppositan-7-one

  摘要：

  Sesquiterpenoids (+)-trans-dracuncuflifoliol (1) and (+)-4-hydroxyoppositan-7-one (2) were prepared stereoselectively from enantiomerically pure (7aR)-7a-methyl-1,2,5,6,7,7a-hexahydro-4H-inden-4-one ((-)-6), whose synthesis was described herein. Conjugate addition of the organocopper (1) reagent 10 to (-)-6, followed by epimerization of the ring junction, generated 3 of the 4 contiguous chiral centers of both natural products. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.01.089

文献信息

• Copper-Catalyzed Asymmetric Conjugate Addition of Trialkylaluminium Reagents to Trisubstituted Enones: Construction of Chiral Quaternary Centers
  作者：Magali Vuagnoux-d'Augustin、Alexandre Alexakis

  DOI：10.1002/chem.200701001

  日期：2007.11.26

  vinylalane species undergo enantioselective conjugate addition to a wide range of 2- or 3-substituted enones (cyclopent-2-enones, cyclohex-2-enones, 3-methyl cyclohept-2-enone) in the presence of catalytic amount of copper salt (copper thiophene carboxylate, [Cu(CH3CN)4]BF4 or [CuOTf]2C6H6) and tropos-phosphoramidite-based ligand. Thus, chiral quaternary centers can be built, with up to 98% ee after rigorous

  在催化作用下，Me3Al，Et3Al和乙烯基丙烷类物质进行对映选择性共轭加成，生成各种2-或3-取代的烯酮（环戊-2-烯酮，环己-2-烯酮，3-甲基环庚-2-烯酮）铜盐（噻吩羧酸铜，[Cu（CH3CN）4] BF4或[CuOTf] 2C6H6）和基于对位亚磷酰胺的配体。因此，经过严格优化实验条件后，可以建立具有高达98％ee的手性四元中心。结果表明，主要的重要参数是试剂引入的顺序。然后，将生成的对映体富集的烯醇铝和手性共轭加合物官能化并用于随后的反应。
• Enantioselective Copper-Catalyzed Conjugate Addition to Trisubstituted Cyclohexenones: Construction of Stereogenic Quaternary Centers
  作者：Magali d?Augustin、La�ticia Palais、Alexandre Alexakis

  DOI：10.1002/anie.200462137

  日期：2005.2.18
• Total syntheses of the sesquiterpenoids (+)-trans-dracunculifoliol and (+)-4-hydroxyoppositan-7-one
  作者：Renata M. Oballa、Rebekah Carson、Susan Lait、Jay A. Cadieux、Joël Robichaud

  DOI：10.1016/j.tet.2005.01.089

  日期：2005.3

  Sesquiterpenoids (+)-trans-dracuncuflifoliol (1) and (+)-4-hydroxyoppositan-7-one (2) were prepared stereoselectively from enantiomerically pure (7aR)-7a-methyl-1,2,5,6,7,7a-hexahydro-4H-inden-4-one ((-)-6), whose synthesis was described herein. Conjugate addition of the organocopper (1) reagent 10 to (-)-6, followed by epimerization of the ring junction, generated 3 of the 4 contiguous chiral centers of both natural products. (c) 2005 Elsevier Ltd. All rights reserved.