3-<2-(2-hydroxyethyl)-4,5-dimethoxyphenyl>-6,7-dimethoxy-2-methylisoquinolin-1-<2H>-one | 136540-25-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-<2-(2-hydroxyethyl)-4,5-dimethoxyphenyl>-6,7-dimethoxy-2-methylisoquinolin-1-<2H>-one
• 英文别名: N-methyl-3-<2-(hydroxyethyl)-4,5-dimethoxyphenyl>-6,7-dimethoxy-1(2H)-isoquinolone；3-<2-(2-hydroxyethyl)-4,5-dimethoxyphenyl>-6,7-dimethoxy-2-methylisoquinolone；1(2H)-Isoquinolinone, 6,7-dimethoxy-3-(2-(2-hydroxyethyl)-4,5-dimethoxyphenyl)-2-methyl-；3-[2-(2-hydroxyethyl)-4,5-dimethoxyphenyl]-6,7-dimethoxy-2-methylisoquinolin-1-one
• CAS: 136540-25-5
• 化学式: C₂₂H₂₅NO₆
• 分子量: 399.444
• InChiKey: RLPARFCHPRIZTF-UHFFFAOYSA-N

物化性质

• 沸点：
  622.2±55.0 °C(Predicted)
• 密度：
  1.226±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  77.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-<2-(2-hydroxyethyl)-4,5-dimethoxyphenyl>-6,7-dimethoxy-2-methylisoquinolin-1-<2H>-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 27.0h， 生成 5-methyl-2,3,8,9-tetramethoxy-5,6-dihydrobenzophenanthridine
  参考文献：
  名称：

  Sazonova, N. M.; Levina, I. I.; Sladkov, V. I., Journal of Organic Chemistry USSR (English Translation), 1991, vol. 27, # 9.2, p. 1751 - 1756

  摘要：

  DOI：
• 作为产物：
  描述：

  3,4-二甲氧基苯乙酸甲酯 在 盐酸 、 lithium aluminium tetrahydride 、 高氯酸 、 三氟化硼乙醚 、 potassium tert-butylate 、 氨 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 3-<2-(2-hydroxyethyl)-4,5-dimethoxyphenyl>-6,7-dimethoxy-2-methylisoquinolin-1-<2H>-one
  参考文献：
  名称：

  A common and general access to berberine and benzo [c] phenanthridine alkaloids

  摘要：

  The S(RN)1 reactions between o-iodobenzamides and the enolate anion from 2-acetyl homoveratric acid lead to key tricyclic compounds which are easily converted to either berberine or benzo [c] phenanthridine ring systems providing thus a high-yielding and versatile access to both classes of alkaloids.

  DOI：

  10.1016/s0040-4020(01)80496-8

文献信息

• Oxidation Reactions of 2′-Functionalized 3-Aryltetrahydro and 3,4-Dihydroisoquinolines
  作者：Nuria Sotomayor、Esther Domínguez、Esther Lete

  DOI：10.1016/0040-4020(95)00827-u

  日期：1995.11

  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.
• Synthesis and antitumor activity of salts of O-methylfagaronine and its structural analog — C-norbenzo[C]phenanthridine methyl chloride
  作者：N. M. Sazonova、I. I. Levina、I. A. Bezrukov、Yu. A. Ershova、V. I. Sladkov、T. S. Safonova、N. N. Suvorov

  DOI：10.1007/bf00772000

  日期：1991.7
• A common and general access to berberine and benzo [c] phenanthridine alkaloids
  作者：René Beugelmans、Michèle Bois-Choussy

  DOI：10.1016/s0040-4020(01)80496-8

  日期：1992.1

  The S(RN)1 reactions between o-iodobenzamides and the enolate anion from 2-acetyl homoveratric acid lead to key tricyclic compounds which are easily converted to either berberine or benzo [c] phenanthridine ring systems providing thus a high-yielding and versatile access to both classes of alkaloids.
• Sazonova, N. M.; Levina, I. I.; Sladkov, V. I., Journal of Organic Chemistry USSR (English Translation), 1991, vol. 27, # 9.2, p. 1751 - 1756
  作者：Sazonova, N. M.、Levina, I. I.、Sladkov, V. I.、Suvorov, N. N.

  DOI：——

  日期：——