(+/-)-1H-1-hydroxy-2,3-dihydro-2,2,3-trimethyl-7-methoxyisoindolium picrate | 134455-60-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: (+/-)-1H-1-hydroxy-2,3-dihydro-2,2,3-trimethyl-7-methoxyisoindolium picrate
• 英文别名: 7-methoxy-2,2,3-trimethyl-1,3-dihydroisoindol-2-ium-1-ol;2,4,6-trinitrophenolate
• CAS: 134455-60-0；134484-93-8
• 化学式: C₆H₂N₃O₇*C₁₂H₁₈NO₂
• 分子量: 436.378
• InChiKey: CHMOWCKXXLEEAP-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.32
• 重原子数：
  31.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  181.94
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (+/-)-1H-1-hydroxy-2,3-dihydro-2,2,3-trimethyl-7-methoxyisoindolium picrate 、 水 生成 2-[1-(dimethylamino)ethyl]-6-methoxybenzaldehyde;2,4,6-trinitrophenol
  参考文献：
  名称：

  CARROLL, JAMES D.;JONES, PAUL R.;BALL, RICHARD G., J. ORG. CHEM., 56,(1991) N3, C. 4208-4213

  摘要：

  DOI：
• 作为产物：
  描述：

  FA198 在 盐酸 、 正丁基锂 作用下， 以 乙醇 、 水 为溶剂， 反应 2.75h， 生成 (+/-)-1H-1-hydroxy-2,3-dihydro-2,2,3-trimethyl-7-methoxyisoindolium picrate
  参考文献：
  名称：

  Novel ring-chain tautomers derived from (o-formylphenyl)ethylamines

  摘要：

  The synthesis and characterization of some (o-formylphenyl)ethylamines are described. Formylation with DMF of regioselectively lithiated N,N-dimethyl-alpha-(m-methoxyphenyl)ethylamine (1) has provided a route to an unusual ring-chain tautomeric system in which the ring has the dihydroisoindolium structure. The ring tautomers, with two chiral centers, consist of unequal amounts of two racemates, which undergo rapid, base-catalyzed interconversion at ambient temperature on the 360-MHz NMR time scale. The geometry and relative energies of the diastereomeric ring structures were estimated from MMP2 calculations. The trans dihydroisoindolium 3,5-dinitrobenzoate (4d) was characterized by X-ray diffraction, and its geometry was compared with that predicted by calculation. From NMR experiments with the simpler amino aldehyde 6, it has been concluded that, although a methoxy or hydroxy substituent ortho to the formyl group is not a structural requirement for ring tautomerism, it serves to favor the ring over the chain tautomer. The (o-formylphenyl)ethyl sulfides 8 and 9, obtained by nucleophilic displacement of the methiodides, show no propensity for ring formation.

  DOI：

  10.1021/jo00013a025