10b-(1-Hydroxy-but-3-enyl)-8,9-dimethoxy-1,5,6,10b-tetrahydro-2H-pyrrolo[2,1-a]isoquinolin-3-one | 854691-48-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: 10b-(1-Hydroxy-but-3-enyl)-8,9-dimethoxy-1,5,6,10b-tetrahydro-2H-pyrrolo[2,1-a]isoquinolin-3-one
• 英文别名: 10b-(1-Hydroxybut-3-enyl)-8,9-dimethoxy-1,2,5,6-tetrahydropyrrolo[2,1-a]isoquinolin-3-one
• CAS: 854691-48-8
• 化学式: C₁₈H₂₃NO₄
• 分子量: 317.385
• InChiKey: JWXJWEAMPQGWRC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  10b-(1-Hydroxy-but-3-enyl)-8,9-dimethoxy-1,5,6,10b-tetrahydro-2H-pyrrolo[2,1-a]isoquinolin-3-one 在 吡啶 、 磺酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以80%的产率得到11-Allyl-8,9-dimethoxy-1,2,5,6-tetrahydro-benzo[d]pyrrolo[1,2-a]azepin-3-one
  参考文献：
  名称：

  A novel 3,4-dihydroisoquinoline annulation: expedient access to isoquinoline heterocycles

  摘要：

  3,4-Dihydroisoquinoline carboxylate I undergoes a smooth annulation with omega-bromopropionate, butyrate or ortho-bromomethyl benzoate 2 to afford the isoquinoline heterocycle 3 upon treatment with potassium tert-butoxide in DMF at -60 degrees C. This novel annulation constitutes a formal direct synthesis of cyclic Reissert equivalent compounds, thus offers an expedient access towards certain medicinally important isoquinoline heterocycles and relevant natural alkaloids, that is, of berberine and erythrina types. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.03.041
• 作为产物：
  描述：

  ethyl 6,7-dimethoxy-3,4-dihydroisoquinoline-1-carboxylate 在 palladium on activated charcoal potassium tert-butylate 、 氢气 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， -78.0~20.0 ℃ 、121.59 kPa 条件下， 反应 6.26h， 生成 10b-(1-Hydroxy-but-3-enyl)-8,9-dimethoxy-1,5,6,10b-tetrahydro-2H-pyrrolo[2,1-a]isoquinolin-3-one
  参考文献：
  名称：

  A novel 3,4-dihydroisoquinoline annulation: expedient access to isoquinoline heterocycles

  摘要：

  3,4-Dihydroisoquinoline carboxylate I undergoes a smooth annulation with omega-bromopropionate, butyrate or ortho-bromomethyl benzoate 2 to afford the isoquinoline heterocycle 3 upon treatment with potassium tert-butoxide in DMF at -60 degrees C. This novel annulation constitutes a formal direct synthesis of cyclic Reissert equivalent compounds, thus offers an expedient access towards certain medicinally important isoquinoline heterocycles and relevant natural alkaloids, that is, of berberine and erythrina types. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.03.041

文献信息

• A novel 3,4-dihydroisoquinoline annulation: expedient access to isoquinoline heterocycles
  作者：Wei-Dong Z. Li、Hua Yang

  DOI：10.1016/j.tet.2005.03.041

  日期：2005.5

  3,4-Dihydroisoquinoline carboxylate I undergoes a smooth annulation with omega-bromopropionate, butyrate or ortho-bromomethyl benzoate 2 to afford the isoquinoline heterocycle 3 upon treatment with potassium tert-butoxide in DMF at -60 degrees C. This novel annulation constitutes a formal direct synthesis of cyclic Reissert equivalent compounds, thus offers an expedient access towards certain medicinally important isoquinoline heterocycles and relevant natural alkaloids, that is, of berberine and erythrina types. (c) 2005 Elsevier Ltd. All rights reserved.