tetramethyl 11b-(2'-furyl)-9,1'-dimethoxy-7,11b-dihydro-6H-pyrido[2,1-a]isoquinoline-1,2,3,4-tetracarboxylate | 1159572-84-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: tetramethyl 11b-(2'-furyl)-9,1'-dimethoxy-7,11b-dihydro-6H-pyrido[2,1-a]isoquinoline-1,2,3,4-tetracarboxylate
• CAS: 1159572-84-5
• 化学式: C₂₇H₂₇NO₁₁
• 分子量: 541.511
• InChiKey: PYTJXJJZAZOQFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.65
• 重原子数：
  39.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  140.04
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为产物：
  描述：

  1-(2-furyl)-6,7-dimethoxy-3,4-dihydroisoquinoline 、 丁炔二酸二甲酯 以 乙腈 为溶剂， 反应 2.0h， 以28%的产率得到tetramethyl 11b-(2'-furyl)-9,1'-dimethoxy-7,11b-dihydro-6H-pyrido[2,1-a]isoquinoline-1,2,3,4-tetracarboxylate
  参考文献：
  名称：

  A new approach to construction of isoindolo[1,2-a]isoquinoline alkaloids Nuevamine, Jamtine, and Hirsutine via IMDAF reaction

  摘要：

  The interaction between 1-furyl-1,2,3,4-tetrahydroisoquinolines and Unsaturated acids derivatives (acryloyl, methacryloyl, and crotonoyl chloride, maleic and citraconic anhydride) was studied. It was shown that the reaction proceeds via amide formation and Subsequent intramolecular Diels-Alder reaction of the furan (IMDAF). The [4+2] cycloaddition proceeded under mild reaction conditions (25-80 degrees C) and afforded only the exo-adduct in a high yield. With this method, a new approach to the isoindolo[1,2-a]isoquinoline system, the basic structural element of alkaloids Jamtine, Hirsutine, and Nuevamine, is proposed. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.02.024

文献信息

• A new approach to construction of isoindolo[1,2-a]isoquinoline alkaloids Nuevamine, Jamtine, and Hirsutine via IMDAF reaction
  作者：Fedor I. Zubkov、Julya D. Ershova、Anna A. Orlova、Vladimir P. Zaytsev、Eugeniya V. Nikitina、Alexandr S. Peregudov、Atash V. Gurbanov、Roman S. Borisov、Victor N. Khrustalev、Abel M. Maharramov、Alexey V. Varlamov

  DOI：10.1016/j.tet.2009.02.024

  日期：2009.5

  The interaction between 1-furyl-1,2,3,4-tetrahydroisoquinolines and Unsaturated acids derivatives (acryloyl, methacryloyl, and crotonoyl chloride, maleic and citraconic anhydride) was studied. It was shown that the reaction proceeds via amide formation and Subsequent intramolecular Diels-Alder reaction of the furan (IMDAF). The [4+2] cycloaddition proceeded under mild reaction conditions (25-80 degrees C) and afforded only the exo-adduct in a high yield. With this method, a new approach to the isoindolo[1,2-a]isoquinoline system, the basic structural element of alkaloids Jamtine, Hirsutine, and Nuevamine, is proposed. (C) 2009 Elsevier Ltd. All rights reserved.