4-cyano-1-methyl-3-methoxyisoquinoline | 130489-41-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 4-cyano-1-methyl-3-methoxyisoquinoline
• 英文别名: 4-Cyano-3-methoxy-1-methylisoquinoline；3-Methoxy-1-methylisoquinoline-4-carbonitrile
• CAS: 130489-41-7
• 化学式: C₁₂H₁₀N₂O
• 分子量: 198.224
• InChiKey: HFUFUWWIHPCJAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  45.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-cyano-3-methoxy-1-methyl-5,6-dihydroisoquinoline 在 mixture of spironaphthalenones 作用下， 以 均三甲苯 为溶剂， 反应 1.0h， 以70%的产率得到4-cyano-1-methyl-3-methoxyisoquinoline
  参考文献：
  名称：

  Dispironaphthalenones and spironaphthalenones as novel dehydrogenation reagents

  摘要：

  Dehydrogenation of a number of dihydroaromatic substrates has been carried out using either dispironaphthalenone 1 or spironaphthalenones 2 & 3 as dehydrogenating agents. The reaction is over in refluxing mesitylene in 1-2 hr and the yields of the aromatised products are fairly good (65-70%).

  DOI：

  10.1016/s0040-4020(01)88233-8

文献信息

• Potassamide induced in situ alkylation of 5,6-dihydroisoquinolines: Structure of products
  作者：Tirumalai R. Kasturi、Subramaniam Arumugam、Lata Mathew

  DOI：10.1016/s0040-4020(01)80377-x

  日期：1993.3

  Potassamide induced in situ alkylation of 1-alkyl-4-cyano-3-methoxy-5,6-dihydroisoquinolines (2a & 2b) with alkyl iodides (CH3I, CH3CH2I & cyclohexyl iodide) gave the 5-alkyl- and 5,9-dialkyl-5,6-dihydroisoquinolines (4a-d & 3a-e), isoquinoline derivatives,(5a-b) and diastereomeric mixture of 4- alkyl-1,2,3,4-tetrahydroisoquinolin-3(2H)-ones (6a-e & 6'a-e). Structures were assigned on the basis of spectral data [Mass, H-1 & C-13 NMR, 2D NOESY & HC-COLOC]. Amide induced in situ alkylation of compounds 3a and 4a with CH3I gave in almost quantitative yield the dimethylated compounds 3d and 3a respectively. While KNH2/liq.NH3 methylation of 1,2- dihydroisoquinoline, 1 with CH3I gave the mixture of compounds, 6a & 6'a and the isoquinoline derivative 5a, NaH/benzene reaction of 1 with CH3I gave exclusively Sa. N-methylation of the mixture of compounds 6a & 6'a with NaH/CH3I gave the methylated derivatives, 7 & 8. A suitable mechanism has been proposed for the formation of products.
• Kasturi, Tirumalai R.; Arumugam, Subramaniam, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1996, vol. 35, # 5, p. 468 - 470
  作者：Kasturi, Tirumalai R.、Arumugam, Subramaniam

  DOI：——

  日期：——
• Kasturi; Jois, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1990, vol. 29, # 7, p. 620 - 623
  作者：Kasturi、Jois

  DOI：——

  日期：——
• Potassamide induced in situ benzylation of 5,6-dihydroisoquinolines: Structure of novel products
  作者：Tirumalai R. Kasturi、Subramaniam Arumugam

  DOI：10.1016/s0040-4020(01)89336-4

  日期：1994.1

  Potassamide induced in situ benzylation of 1-alkyl-4-cyano-3-methoxy-5,6-dihydroisoquinolines (1a-b) with benzyl iodide gave the 5-benzyl-, 5,9-dibenzyl- and 4,4-dibenzyl-5,6-dihydroisoquinolines (9a-b, 8a-b and 10a-b), isoquinoline derivatives (4a-b) and diastereomeric mixture of 4-benzyl-1,2,3,4-tetrahydroisoquinolin-3(2H)-ones (11a-b & 11'a-b). Structures were assigned on the basis of spectral data [Mass, H-1 & C-13 NMR, 2D NOESY]. A few reactions carried out to transform the diastereomeric mixture of compounds 11a and 11's to the spirobenzylisoquinoline system 7a isomeric with naturally occurring ochotensane system ga are discussed.
• KASTURI, T. R.;JOIS, H. R. Y., INDIAN J. CHEM. B, 29,(1990) N, C. 620-623
  作者：KASTURI, T. R.、JOIS, H. R. Y.

  DOI：——

  日期：——