(S)-6-methoxy-3-methyl-2,3-dihydro-1H-inden-1-one | 210759-99-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (S)-6-methoxy-3-methyl-2,3-dihydro-1H-inden-1-one
• 英文别名: (3S)-6-methoxy-3-methyl-2,3-dihydroinden-1-one
• CAS: 210759-99-2
• 化学式: C₁₁H₁₂O₂
• 分子量: 176.215
• InChiKey: XITJWOSJNCBUDJ-ZETCQYMHSA-N

物化性质

• 沸点：
  286.9±39.0 °C(Predicted)
• 密度：
  1.108±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  (S)-6-methoxy-3-methyl-2,3-dihydro-1H-inden-1-one 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 1.0h， 以94%的产率得到(3S)-6-methoxy-3-methyl-2,3-dihydro-1H-inden-1-ol
  参考文献：
  名称：

  1,3-Hydron Transfer in Some 5- or 7-Substituted 1-Methylindenes. Reaction Rates and Kinetic Isotope Effects.

  摘要：

  Rate constants and primary deuterium kinetic isotope effects (KIEs) have been determined for the base-catalysed 1,3-hydrotropic rearrangements of 1-methyl-5-nitroindene (12), 1-methyl-7-nitroindene (13), 5-methoxy-1-methylindene (14) and 5-fluoro-1-methylindene (15) in o-dichlorobenzene at 20 degrees C. The tertiary amine 1,4-diazabicyclo [2.2.2]octane( DABCO) was used as catalyst. The kinetics were followed by polarimetry using the isotopic quasi-racemate method. The rearrangement of 13 was also investigated by H-1 NMR kinetic experiments. The reaction rate correlates, as expected, with the electronic effect of the substituent ranging from a large increase for the 5-nitro substrate to a small decrease for the methoxy compound as compared with the unsubstituted 1-methylindene. The KIEs vary as predicted from the Melander-Westheimer postulate showing an increase with reaction rate from 5.57 to 8.56. The syntheses of the (+)-(S)-form of the 5- or 7-substituted indenes and the (-)-(R)-form of the deuteriated analogues are also reported.

  DOI：

  10.3891/acta.chem.scand.52-0911
• 作为产物：
  描述：

  (S)-3-methyl-1-indanone 在 硫酸 、 potassium carbonate 、 potassium nitrate 、 calcium chloride 、 锌 、 sodium nitrite 作用下， 以 乙醇 、 水 、 丙酮 为溶剂， 反应 12.0h， 生成 (S)-6-methoxy-3-methyl-2,3-dihydro-1H-inden-1-one
  参考文献：
  名称：

  1,3-Hydron Transfer in Some 5- or 7-Substituted 1-Methylindenes. Reaction Rates and Kinetic Isotope Effects.

  摘要：

  Rate constants and primary deuterium kinetic isotope effects (KIEs) have been determined for the base-catalysed 1,3-hydrotropic rearrangements of 1-methyl-5-nitroindene (12), 1-methyl-7-nitroindene (13), 5-methoxy-1-methylindene (14) and 5-fluoro-1-methylindene (15) in o-dichlorobenzene at 20 degrees C. The tertiary amine 1,4-diazabicyclo [2.2.2]octane( DABCO) was used as catalyst. The kinetics were followed by polarimetry using the isotopic quasi-racemate method. The rearrangement of 13 was also investigated by H-1 NMR kinetic experiments. The reaction rate correlates, as expected, with the electronic effect of the substituent ranging from a large increase for the 5-nitro substrate to a small decrease for the methoxy compound as compared with the unsubstituted 1-methylindene. The KIEs vary as predicted from the Melander-Westheimer postulate showing an increase with reaction rate from 5.57 to 8.56. The syntheses of the (+)-(S)-form of the 5- or 7-substituted indenes and the (-)-(R)-form of the deuteriated analogues are also reported.

  DOI：

  10.3891/acta.chem.scand.52-0911

文献信息

• Asymmetric Induction in Hydroacylation by Cooperative Iminium Ion–Transition-Metal Catalysis
  作者：Ettore J. Rastelli、Ngoc T. Truong、Don M. Coltart

  DOI：10.1021/acs.orglett.6b02825

  日期：2016.11.4

  has been achieved through the merger of iminium ion catalysis and transition-metal catalysis such that asymmetric induction derives from a readily accessible, inexpensive chiral nonracemic secondary amine catalyst rather than a chiral nonracemic phosphine as is typical of conventional asymmetric hydroacylation methods.

  描述了铑催化的对映选择性加氢酰化的新策略。这是通过将亚胺离子催化和过渡金属催化合并而实现的，使得不对称诱导衍生自易于获得的廉价手性非外消旋仲胺催化剂，而不是常规不对称加氢酰化方法中典型的手性非外消旋膦。
• 1,3-Hydron Transfer in Some 5- or 7-Substituted 1-Methylindenes. Reaction Rates and Kinetic Isotope Effects.
  作者：Marie Aune、Rolf Danielsson、Anita Hussénius、Per Ryberg、Ása Guorún Kristjánsdóttir、Olle Matsson、Kurt V. Mikkelsen、Alexander Senning

  DOI：10.3891/acta.chem.scand.52-0911

  日期：——

  Rate constants and primary deuterium kinetic isotope effects (KIEs) have been determined for the base-catalysed 1,3-hydrotropic rearrangements of 1-methyl-5-nitroindene (12), 1-methyl-7-nitroindene (13), 5-methoxy-1-methylindene (14) and 5-fluoro-1-methylindene (15) in o-dichlorobenzene at 20 degrees C. The tertiary amine 1,4-diazabicyclo [2.2.2]octane( DABCO) was used as catalyst. The kinetics were followed by polarimetry using the isotopic quasi-racemate method. The rearrangement of 13 was also investigated by H-1 NMR kinetic experiments. The reaction rate correlates, as expected, with the electronic effect of the substituent ranging from a large increase for the 5-nitro substrate to a small decrease for the methoxy compound as compared with the unsubstituted 1-methylindene. The KIEs vary as predicted from the Melander-Westheimer postulate showing an increase with reaction rate from 5.57 to 8.56. The syntheses of the (+)-(S)-form of the 5- or 7-substituted indenes and the (-)-(R)-form of the deuteriated analogues are also reported.