3,4-dihydro-3-(3,4-dimethoxyphenyl)-6,7-dimethoxyisoquinoline | 20232-47-7

• 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: 3,4-dihydro-3-(3,4-dimethoxyphenyl)-6,7-dimethoxyisoquinoline
• 英文别名: 3-(3,4-dimethoxyphenyl)-6,7-dimethoxy-3,4-dihydroisoquinoline；6,7-Dimethoxy-3-<3,4-dimethoxy-phenyl>-3,4-dihydro-isochinolin
• CAS: 20232-47-7
• 化学式: C₁₉H₂₁NO₄
• 分子量: 327.38
• InChiKey: LTUCQMHRCMZZNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  49.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,4-dihydro-3-(3,4-dimethoxyphenyl)-6,7-dimethoxyisoquinoline 在 氢氧化钾 、 air 作用下， 以 二甲基亚砜 为溶剂， 反应 0.75h， 以90%的产率得到3-(3,4-dimethoxyphenyl)-6,7-dimethoxyisoquinoline
  参考文献：
  名称：

  Oxidation Reactions of 2′-Functionalized 3-Aryltetrahydro and 3,4-Dihydroisoquinolines

  摘要：

  Several 2'-functionalized 3-arylisoquinolines in different oxidation stages have been prepared. Fremy's salt or I-2/NaAcO oxidation of 2'-functionalized 3-aryltetrahydroisoquinolines always stops at the 3,4-dihydroisquinoline stage; however, better yields and shorter reaction Limes are obtained with iodine. Air/KOH/DMSO oxidation of 3,4-dihydroisoquinolines furnished the aromatic derivatives with concomitant cleavage of the TBDPS group. While 3-arylisoquinolin-1-(2H)-ones are obtained by air oxidation of 3,4-dihydroisquinolinium salts, the use of DDQ in dioxane resulted in a selective dehydrogenation to the corresponding N-substituted isoquinolinium salts.

  DOI：

  10.1016/0040-4020(95)00827-u
• 作为产物：
  描述：

  1,2-bis(3,4-dimethoxyphenyl)ethanone 在 硫酸 、 三氯化铁 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 3,4-dihydro-3-(3,4-dimethoxyphenyl)-6,7-dimethoxyisoquinoline
  参考文献：
  名称：

  A modified Bischler-Napieralski procedure for the synthesis of 3-aryl-3,4-dihydroisoquinolines

  摘要：

  A modification of the Bischler-Napieralski reaction for the cyclization of (1,2-diphenylethyl)amides to the 3-aryl-3,4-dihydroisoquinolines is presented. Elimination of the amide group as the nitrile via the retro-Ritter reaction is avoided by its conversion to an N-acyliminium intermediate with oxalyl chloride-FeCl3. Removal of the oxalyl group in refluxing MeOH-sulfuric acid provides the 3,4-dihydroisoquinolines in moderate to high yields. The method is also highly effective with (2-phenylethyl)amides.

  DOI：

  10.1021/jo00021a014

文献信息

• Ivanov, Iliyan; Venkov, Atanas, Heterocycles, 2001, vol. 55, # 8, p. 1569 - 1580
  作者：Ivanov, Iliyan、Venkov, Atanas

  DOI：——

  日期：——
• Domingues, Esther; Lete, Esther, Journal of Heterocyclic Chemistry, 1984, vol. 21, p. 525 - 528
  作者：Domingues, Esther、Lete, Esther

  DOI：——

  日期：——
• Narasimhan, N. S.; Wadia, M. S.; Shete, N. R., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1980, vol. 19, # 7, p. 556 - 560
  作者：Narasimhan, N. S.、Wadia, M. S.、Shete, N. R.

  DOI：——

  日期：——
• NARASIMHAN N. S.; WADIA M. S.; SHETE N. R., INDIAN J. CHEM., 1980, B 19, NO 7, 556-560
  作者：NARASIMHAN N. S.、 WADIA M. S.、 SHETE N. R.

  DOI：——

  日期：——
• DOMINGUEZ, E.;LETE, E., HETEROCYCLES, 1983, 20, N 7, 1247-1254
  作者：DOMINGUEZ, E.、LETE, E.

  DOI：——

  日期：——