8-isopropoxy-9,11,12-trimethoxy-2-methyl-3,4-dihydro-2H-naphtho[2,1-f]isoquinolin-1-one | 624720-95-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 8-isopropoxy-9,11,12-trimethoxy-2-methyl-3,4-dihydro-2H-naphtho[2,1-f]isoquinolin-1-one
• 英文别名: 9,11,12-Trimethoxy-2-methyl-8-propan-2-yloxy-3,4-dihydronaphtho[2,1-f]isoquinolin-1-one
• CAS: 624720-95-2
• 化学式: C₂₄H₂₇NO₅
• 分子量: 409.482
• InChiKey: VQCZZLRBPAUSCM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  57.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  8-isopropoxy-9,11,12-trimethoxy-2-methyl-3,4-dihydro-2H-naphtho[2,1-f]isoquinolin-1-one 在 lithium aluminium tetrahydride 、 三氯化硼 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.25h， 生成 9,11-二甲氧基-2-甲基-3,4-二氢-1H-萘并[6,5-f]异喹啉-8,12-二醇
  参考文献：
  名称：

  First total syntheses of the 1,2,3,4-tetrahydronaphtho[2,1-f]isoquinolines annoretine and litebamine

  摘要：

  We describe here the first total synthesis of the two natural 1,2,3,4-tetrahydronaphtho[2,1-f]isoquinolines, annoretine and litebamine, from [2-(2-styrylphenyl)ethyl]methylcarbamic acid ethyl esters. The key steps were the Bischler-Napieralski cyclization to form the isoquinoline unit and photocyclization of the resulting 2-methyl-5-styryl-3,4-dihydro-2H-isoquinolin-1-ones to 2-methyl-3,4-dihydro-2H-naphtho[2,1-f]isoquinolin-1-ones. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)01135-9
• 作为产物：
  描述：

  5-[2-(3-isopropoxy-4-methoxyphenyl)vinyl]-7,8-dimethoxy-2-methyl-3,4-dihydro-2H-isoquinolin-1-one 在 air 、 碘 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 3.0h， 以41%的产率得到8-isopropoxy-9,11,12-trimethoxy-2-methyl-3,4-dihydro-2H-naphtho[2,1-f]isoquinolin-1-one
  参考文献：
  名称：

  First total syntheses of the 1,2,3,4-tetrahydronaphtho[2,1-f]isoquinolines annoretine and litebamine

  摘要：

  We describe here the first total synthesis of the two natural 1,2,3,4-tetrahydronaphtho[2,1-f]isoquinolines, annoretine and litebamine, from [2-(2-styrylphenyl)ethyl]methylcarbamic acid ethyl esters. The key steps were the Bischler-Napieralski cyclization to form the isoquinoline unit and photocyclization of the resulting 2-methyl-5-styryl-3,4-dihydro-2H-isoquinolin-1-ones to 2-methyl-3,4-dihydro-2H-naphtho[2,1-f]isoquinolin-1-ones. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)01135-9

文献信息

• First total syntheses of the 1,2,3,4-tetrahydronaphtho[2,1-f]isoquinolines annoretine and litebamine
  作者：M.Carme Pampı́n、Juan C Estévez、Ramón J Estévez、Rafael Suau、Luis Castedo

  DOI：10.1016/s0040-4020(03)01135-9

  日期：2003.9

  We describe here the first total synthesis of the two natural 1,2,3,4-tetrahydronaphtho[2,1-f]isoquinolines, annoretine and litebamine, from [2-(2-styrylphenyl)ethyl]methylcarbamic acid ethyl esters. The key steps were the Bischler-Napieralski cyclization to form the isoquinoline unit and photocyclization of the resulting 2-methyl-5-styryl-3,4-dihydro-2H-isoquinolin-1-ones to 2-methyl-3,4-dihydro-2H-naphtho[2,1-f]isoquinolin-1-ones. (C) 2003 Elsevier Ltd. All rights reserved.