7-benzyloxy-1-(3-benzyloxy-4-methoxy-benzyl)-6-methoxy-3,4-dihydro-isoquinoline | 20323-85-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 7-benzyloxy-1-(3-benzyloxy-4-methoxy-benzyl)-6-methoxy-3,4-dihydro-isoquinoline
• 英文别名: 7-Benzyloxy-1-(3-benzyloxy-4-methoxy-benzyl)-6-methoxy-3,4-dihydro-isochinolin；7-Benzyloxy-1-(3-benzyloxy-4-methoxy-benzyl)-3,4-dihydro-6-methoxy-isochinolin；1-(3-Benzyloxy-4-methoxy-benzyl)-6-methoxy-7-benzyloxy-3,4-dihydroisochinolin；7-Benzyloxy-1-(3-benzyloxy-4-methoxy-benzyl)-6-methoxy-3,4-dihydroisochinolin；7-Benzyloxy-1-(3-benzyloxy-4-methoxybenzyl)-3,4-dihydro-6-methoxy-isochinolin；1-(3-Benzyloxy-4-methoxybenzyl)-6-methoxy-7-benzyloxy-3,4-dihydroisochinolin；6-Methoxy-1-[(4-methoxy-3-phenylmethoxyphenyl)methyl]-7-phenylmethoxy-3,4-dihydroisoquinoline
• CAS: 20323-85-7
• 化学式: C₃₂H₃₁NO₄
• 分子量: 493.602
• InChiKey: AFLGERFIBQNORH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  49.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-benzyloxy-1-(3-benzyloxy-4-methoxy-benzyl)-6-methoxy-3,4-dihydro-isoquinoline 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 、 sodium hydride 、 碳酸氢钠 、 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 、 1,2-二氯乙烷 、 乙腈 为溶剂， 20.0 ℃ 、517.11 kPa 条件下， 反应 94.0h， 生成 14-(3-acetoxy-4-methoxyphenyl)-3,12-diacetoxy-2,11-dimethoxy-6H-chromeno[4',3':4,5]pyrrolo[2,1-a]isoquinolin-6-one
  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 、 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 为溶剂， 反应 7.0h， 生成 7-benzyloxy-1-(3-benzyloxy-4-methoxy-benzyl)-6-methoxy-3,4-dihydro-isoquinoline
  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

• Gopinath et al., Chemische Berichte, 1959, vol. 92, p. 1657,1660
  作者：Gopinath et al.

  DOI：——

  日期：——
• 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.