4-Cyano-1-ethyl-3-methoxyisoquinoline | 74745-47-4

• 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-ethyl-3-methoxyisoquinoline
• 英文别名: 1-Ethyl-3-methoxyisoquinoline-4-carbonitrile
• CAS: 74745-47-4
• 化学式: C₁₃H₁₂N₂O
• 分子量: 212.251
• InChiKey: UHIISIZKNMMZQW-UHFFFAOYSA-N

物化性质

• 熔点：
  96-98 °C
• 沸点：
  373.3±42.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 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：

  2-丙酰环己酮 在 sodium tetrahydroborate 、 sodium dichromate 、 硫酸 、 三氯化铁 、 对甲苯磺酸 、 potassium amide 、 silver(l) oxide 作用下， 以 四氢呋喃 、 甲醇 、 氨 、 溶剂黄146 、 苯 为溶剂， 反应 24.5h， 生成 4-Cyano-1-ethyl-3-methoxyisoquinoline
  参考文献：
  名称：

  Kasturi, Tirumalai Rangachar; Krishnan, Lalitha; Prasad, Ramanujam Srinivasa, Journal of the Chemical Society. Perkin transactions I, 1982, p. 63 - 68

  摘要：

  DOI：

文献信息

• Amide catalysed facile isomerization of 5,6-dihydroisoquinolines: synthesis of stable 1,2-dihydroisoquinolines.
  作者：T.R. Kasturi、Lalitha Krishnan

  DOI：10.1016/s0040-4039(00)71528-0

  日期：1980.1

  Stable 1,2-dihydroisoquinolines have been synthesized by an amide catalysed novel isomerization reaction of 5,6-dihydroisoquinolines.

  通过酰胺催化的5，6-二氢异喹啉的新型异构化反应已经合成了稳定的1，2-二氢异喹啉。
• 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.
• 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.; KRISHNAN L., TETRAHEDRON LETT., 1980, 21, NO 9, 865-866
  作者：KASTURI T. R.、 KRISHNAN L.

  DOI：——

  日期：——
• KASTURI, TIRUMALAI, RANGACHAR;KRISHNAN, LALITHA;PRASAD, RAMANUJAM, SRINIV+, J. CHEM. SOC. PERKIN. TRANS., 1982, N 1, 63-68
  作者：KASTURI, TIRUMALAI, RANGACHAR、KRISHNAN, LALITHA、PRASAD, RAMANUJAM, SRINIV+

  DOI：——

  日期：——