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