4-methyl-3,4-dihydro-isoquinoline | 86457-01-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢异喹啉
• 英文名称: 4-methyl-3,4-dihydro-isoquinoline
• 英文别名: 4-Methyl-3,4-dihydro-isochinolin；3,4-dihydro-4-methylisoquinoline；4-Methyl-3,4-dihydroisoquinoline
• CAS: 86457-01-4
• 化学式: C₁₀H₁₁N
• 分子量: 145.204
• InChiKey: WYKKMLDQCFENNJ-UHFFFAOYSA-N

物化性质

• 沸点：
  111-112 °C(Press: 12 Torr)
• 密度：
  1.02 g/cm3(Temp: 25 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-methyl-3,4-dihydro-isoquinoline 在 钯 作用下， 生成 4-甲基异喹啉
  参考文献：
  名称：

  Spaeth et al., Chemische Berichte, 1930, vol. 63, p. 134,136

  摘要：

  DOI：
• 作为产物：
  描述：

  rac-N-(2-phenylpropyl)formamide 在 PPA 作用下， 生成 4-methyl-3,4-dihydro-isoquinoline
  参考文献：
  名称：

  The Rearrangement of Isoquinoline-N-Oxides. II. Observations with N-Hydroxyisocarbostyrils and Other Substituted Derivatives¹

  摘要：

  DOI：

  10.1021/ja01546a060

文献信息

• Pyrimidoisoquinoline derivatives useful for treating allergies
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US04673676A1

  公开（公告）日：1987-06-16

  Pyrimidoisoquinoline/compounds of the formula: ##STR1## where R.sup.1 is H, halogen or lower alkyl, R.sup.2 is NH.sub.2, NO.sub.2 or acylamino and R.sup.3 is carboxy or protected carboxy, pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof are disclosed in this application. Also disclosed is a method of treating allergies by administering the compounds of this invention.

  本申请揭示了公式为：##STR1##其中R.sup.1为H、卤素或较低烷基，R.sup.2为NH.sub.2、NO.sub.2或酰基氨基，R.sup.3为羧基或保护羧基的吡咯并异喹啉/化合物，其药学上可接受的盐以及其药物组合物。本发明还揭示了通过给予本发明的化合物来治疗过敏的方法。
• Thermal electrocyclic reactions of 2-aza-1,3-butadiene derivatives. A new N-heterocyclic annelation
  作者：C. K. Govindan、Grant Taylor

  DOI：10.1021/jo00174a036

  日期：1983.12
• Oxidation of 1,2,3,4-Tetrahydroisoquinolines to 3,4-Dihydroisoquinolines with Molecular Oxygen Catalyzed by Copper(Ö†) Chloride
  作者：Masao Shimizu、Hideo Orita、Takashi Hayakawa、Kunio Suzuki、Katsuomi Takehira

  DOI：10.3987/com-94-6991

  日期：——

  A catalytic oxidation system, a CuCl2-O-2 system, was efficient for dehydrogenation of 1,2,3,4-tetrahydroisoquinolines to 3,4-dihydroisoquinolines. Oxidation of 1,2,3,4-tetrahydroquinoline was also carried out.
• Conformational Analysis. 50. <i>C</i>-Methyl-1,2,3,4-tetrahydroisoquinolines
  作者：Edward M. Olefirowicz、Ernest L. Eliel

  DOI：10.1021/jo971257r

  日期：1997.12.1

  Conformational equilibria in 1-, 3-, and 4-methyl-1,2,3,4-tetrahydroisoquinolines (THIQs) and the diastereomeric pairs of their 1,3- and 1,4-dimethyl homologs have been determined by measurement of H-3/H-4(trans) coupling constants and have been confirmed by molecular mechanics [MMP2(85]) calculations. The experimental -Delta G degrees values (a --> e) for the monomethyl compounds (computed values in parentheses) in kcal mol(-1) are Me-1, 0.56 (0.46); Me-3, 1.63 (1.53); and Me-4, -0.32 (-0.22). Agreement of experimental and calculated values is very goad as is the additivity of values for the dimethyl compounds (Table 1). Values for the corresponding hydrochlorides are Me-1, 0.19 (-0.34); Me-3, 1.15 (1.46); and Me-4, 0.35 (0.10) kcal mol(-1). The less than satisfactory agreement of experimental with computed data here is probably due to neglect of solvation. The very small or negative Delta G degrees values for Me-1 and Me-4 were ascribed not only to the pseudoaxial (rather than axial) nature of Me(ax) and the absence of a syn-axial hydrogen on the side of the benzene ring but also to a peri interaction with H(8) and H(5), respectively, destabilizing equatorial methyl at positions 1 and 4. This was confirmed by comparing computed conformational energy values with values at corresponding positions in Delta(3,4)-tetrahydropyridines (THPs). While Delta G degrees in the two series is the same for Me-3 (THIQ numbering), that for Me-1 and Me-4 is considerably smaller in the THIQ than in the THP series which latter is devoid of peri hydrogens.
• Pyrimidoisoquinoline derivatives
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：EP0143001B1

  公开（公告）日：1991-04-10