(S)-6-fluoro-3-methylindan-1-one | 210760-03-5

• 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-fluoro-3-methylindan-1-one
• 英文别名: (3S)-6-fluoro-3-methyl-2,3-dihydroinden-1-one
• CAS: 210760-03-5
• 化学式: C₁₀H₉FO
• 分子量: 164.179
• InChiKey: RXBRIKMPIAEXLF-LURJTMIESA-N

物化性质

• 沸点：
  231.9±39.0 °C(Predicted)
• 密度：
  1.179±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-6-fluoro-3-methylindan-1-one 在 sodium tetrahydroborate 、 对甲苯磺酸 作用下， 以 甲醇 、 苯 为溶剂， 反应 3.5h， 生成 3-(2,3-二羟基丙基)脱氧尿苷
  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 盐酸 、 tetrafluoroboric acid 、 硫酸 、 potassium nitrate 、 calcium chloride 、 锌 、 sodium nitrite 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 54.0h， 生成 (S)-6-fluoro-3-methylindan-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

• 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.