ethyl 1-(3-benzyloxy-4-methoxyphenyl)-2-(2,4-dibenzyloxy-5-methoxyphenyl)-9-benzyloxy-8-methoxy-5,6-dihydropyrrolo[2,1-a]isoquinoline-3-carboxylate | 919082-40-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: ethyl 1-(3-benzyloxy-4-methoxyphenyl)-2-(2,4-dibenzyloxy-5-methoxyphenyl)-9-benzyloxy-8-methoxy-5,6-dihydropyrrolo[2,1-a]isoquinoline-3-carboxylate
• 英文别名: Ethyl 8-methoxy-2-[5-methoxy-2,4-bis(phenylmethoxy)phenyl]-1-(4-methoxy-3-phenylmethoxyphenyl)-9-phenylmethoxy-5,6-dihydropyrrolo[2,1-a]isoquinoline-3-carboxylate
• CAS: 919082-40-9
• 化学式: C₅₈H₅₃NO₉
• 分子量: 908.06
• InChiKey: OJKAJMGMCYDJEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.9
• 重原子数：
  68
• 可旋转键数：
  20
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  95.8
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  ethyl 1-(3-benzyloxy-4-methoxyphenyl)-2-(2,4-dibenzyloxy-5-methoxyphenyl)-9-benzyloxy-8-methoxy-5,6-dihydropyrrolo[2,1-a]isoquinoline-3-carboxylate 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 20.0 ℃ 、517.1 kPa 条件下， 生成
  参考文献：
  名称：

  Total Synthesis of Natural and Unnatural Lamellarins with Saturated and Unsaturated D-Rings

  摘要：

  Twenty-eight natural and unnatural lamellarins with either a saturated or an unsaturated D-ring were synthesized according to our developed synthetic route. The key step involved the Michael addition/ring closure (Mi-RC) of the benzyldihydroisoquinoline and alpha-nitrocinnamate derivatives, which provided the 2-carboethoxypyrrole intermediates in moderate to good yields (up to 78% yield). Subsequent hydrogenolysis/lactonization furnished lamellarins with a saturated D-ring in excellent yields (up to 93% yield). DDQ oxidation of the saturated lamellarin acetates led directly to the corresponding unsaturated analogues in 54-95% yield. In addition, only two steps in our developed strategy require column chromatography.

  DOI：

  10.1021/jo061810h
• 作为产物：
  描述：

  (3-苄氧基-4-甲氧基-苯基)乙酸 在 草酰氯 、 碳酸氢钠 、 sodium carbonate 、 N,N-二甲基甲酰胺 、 三氯氧磷 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 25.0h， 生成 ethyl 1-(3-benzyloxy-4-methoxyphenyl)-2-(2,4-dibenzyloxy-5-methoxyphenyl)-9-benzyloxy-8-methoxy-5,6-dihydropyrrolo[2,1-a]isoquinoline-3-carboxylate
  参考文献：
  名称：

  Total Synthesis of Natural and Unnatural Lamellarins with Saturated and Unsaturated D-Rings

  摘要：

  Twenty-eight natural and unnatural lamellarins with either a saturated or an unsaturated D-ring were synthesized according to our developed synthetic route. The key step involved the Michael addition/ring closure (Mi-RC) of the benzyldihydroisoquinoline and alpha-nitrocinnamate derivatives, which provided the 2-carboethoxypyrrole intermediates in moderate to good yields (up to 78% yield). Subsequent hydrogenolysis/lactonization furnished lamellarins with a saturated D-ring in excellent yields (up to 93% yield). DDQ oxidation of the saturated lamellarin acetates led directly to the corresponding unsaturated analogues in 54-95% yield. In addition, only two steps in our developed strategy require column chromatography.

  DOI：

  10.1021/jo061810h

文献信息

• Total Synthesis of Natural and Unnatural Lamellarins with Saturated and Unsaturated D-Rings
  作者：Poonsakdi Ploypradith、Thaninee Petchmanee、Poolsak Sahakitpichan、Nichole D. Litvinas、Somsak Ruchirawat

  DOI：10.1021/jo061810h

  日期：2006.12.1

  Twenty-eight natural and unnatural lamellarins with either a saturated or an unsaturated D-ring were synthesized according to our developed synthetic route. The key step involved the Michael addition/ring closure (Mi-RC) of the benzyldihydroisoquinoline and alpha-nitrocinnamate derivatives, which provided the 2-carboethoxypyrrole intermediates in moderate to good yields (up to 78% yield). Subsequent hydrogenolysis/lactonization furnished lamellarins with a saturated D-ring in excellent yields (up to 93% yield). DDQ oxidation of the saturated lamellarin acetates led directly to the corresponding unsaturated analogues in 54-95% yield. In addition, only two steps in our developed strategy require column chromatography.