9-((1,3-dioxoisoindolin-2-yl)methyl)-3-(6-methoxy-4-methyl-6,7-dihydro-[1,3]dioxolo[4,5-h]isoquinolin-7-yl)methyl-2-(1,3-dioxoisoindolin-2-yl)acetate | 1003600-18-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 9-((1,3-dioxoisoindolin-2-yl)methyl)-3-(6-methoxy-4-methyl-6,7-dihydro-[1,3]dioxolo[4,5-h]isoquinolin-7-yl)methyl-2-(1,3-dioxoisoindolin-2-yl)acetate
• 英文别名: [9-[(1,3-Dioxoisoindol-2-yl)methyl]-5-methoxy-4-methyl-6,7-dihydro-[1,3]dioxolo[4,5-h]isoquinolin-7-yl]methyl 2-(1,3-dioxoisoindol-2-yl)acetate；[9-[(1,3-dioxoisoindol-2-yl)methyl]-5-methoxy-4-methyl-6,7-dihydro-[1,3]dioxolo[4,5-h]isoquinolin-7-yl]methyl 2-(1,3-dioxoisoindol-2-yl)acetate
• CAS: 1003600-18-7
• 化学式: C₃₂H₂₅N₃O₉
• 分子量: 595.565
• InChiKey: UUQFTLIVXDRYKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  44
• 可旋转键数：
  8
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  141
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  9-((1,3-dioxoisoindolin-2-yl)methyl)-3-(6-methoxy-4-methyl-6,7-dihydro-[1,3]dioxolo[4,5-h]isoquinolin-7-yl)methyl-2-(1,3-dioxoisoindolin-2-yl)acetate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以81%的产率得到[(7S,9R)-9-[(1,3-dioxoisoindol-2-yl)methyl]-5-methoxy-4-methyl-6,7,8,9-tetrahydro-[1,3]dioxolo[4,5-h]isoquinolin-7-yl]methyl 2-(1,3-dioxoisoindol-2-yl)acetate
  参考文献：
  名称：

  Synthetic studies towards (±)-phthalascidin 650: synthesis of a fully functionalized N-protected-α-amino-aldehyde

  摘要：

  An efficient synthesis of fully functionalized N-protected alpha-amino-aldehyde (+/-)-13 as synthetic precursor of the tetra-hydroisoquinoline alkaloid phthalascidin 650 is reported. Starting from sesamol 6, 11 steps are required to give rise to the desired N-protected alpha-amino-aldehyde (+/-)-13 in 25% overall yield. This synthetic strategy involves the elaboration of fully functionalized aromatic aldehyde 7 and its transformation into an alpha-amino-alcohol through a Knoevenagel condensation. The phthalimidomethyl derivative (+/-)-11 was then synthesised from 8 by a Bischler-Napieralski reaction, a diastereoselective hydrogenation of the resultant dihydroisoquinoline and transformed into the corresponding N-protected alpha-amino-aldehyde (+/-)-13. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.10.111
• 作为产物：
  描述：

  2-(2-(1,3-dioxoisoindolin-2-yl)acetamido)-3-(6-methoxy-7-methylbenzo[d][1,3]dioxol-5-yl)propyl-2-(1,3-dioxoisoindolin-2-yl)acetate 在 N,N-二甲基甲酰胺 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以95%的产率得到9-((1,3-dioxoisoindolin-2-yl)methyl)-3-(6-methoxy-4-methyl-6,7-dihydro-[1,3]dioxolo[4,5-h]isoquinolin-7-yl)methyl-2-(1,3-dioxoisoindolin-2-yl)acetate
  参考文献：
  名称：

  （±）-酞菁622的合成

  摘要：

  公开了作为邻苯二酚650的邻苯二酚四氢异喹啉结构的合成前体的官能化酚类α-氨基醇（±）-8和（±）-16的合成。（±） - 8是在5个步骤制备由市售芝麻酚。从3-甲基邻苯二酚5开始，经过8个步骤，以27％的总收率合成了酚类α-氨基醇（±）-16。该合成策略涉及对完全官能化的芳族醛13进行精细加工，并将其转化为酚类α-氨基醇（±）-16通过Knoevenagel缩合反应，同时还原硝基烯酮和酯官能团，以及苄基保护基的氢解。在另外4个步骤后获得了五环（±）-4。在酚类α-氨基醇（±）-16和N-保护的α-氨基醛4之间进行Pictet-Spengler环化反应，可以得到（1,3'）- N-甲基化和N-化的双-四氢异喹啉17 Fmoc已删除。最后一步是Swern氧化，可实现预期的分子内缩合。

  DOI：

  10.1007/s11426-010-4075-z

文献信息

• Synthesis of (±)-phthalascidin 622
  作者：R. Razafindrabe Christian、Aubry Sylvain、Bourdon Benjamin、Andriantsiferana Marta、Pellet-Rostaing Stephane、Lemaire Marc

  DOI：10.1007/s11426-010-4075-z

  日期：2010.9

  synthesis of functionalized phenolic α-amino-alcohols (±)-8 and (±)-16 as synthetic precursors of the catechol tetrahydroisoquinoline structure of phthalascidin 650 was disclosed. (±)-8 was prepared in 5 steps from the commercially available sesamol. Starting from 3-methyl catechol 5, 8 steps gave rise to the synthesis of phenolic α-amino-alcohol (±)-16 in 27% overall yield. This synthetic strategy involved

  公开了作为邻苯二酚650的邻苯二酚四氢异喹啉结构的合成前体的官能化酚类α-氨基醇（±）-8和（±）-16的合成。（±） - 8是在5个步骤制备由市售芝麻酚。从3-甲基邻苯二酚5开始，经过8个步骤，以27％的总收率合成了酚类α-氨基醇（±）-16。该合成策略涉及对完全官能化的芳族醛13进行精细加工，并将其转化为酚类α-氨基醇（±）-16通过Knoevenagel缩合反应，同时还原硝基烯酮和酯官能团，以及苄基保护基的氢解。在另外4个步骤后获得了五环（±）-4。在酚类α-氨基醇（±）-16和N-保护的α-氨基醛4之间进行Pictet-Spengler环化反应，可以得到（1,3'）- N-甲基化和N-化的双-四氢异喹啉17 Fmoc已删除。最后一步是Swern氧化，可实现预期的分子内缩合。
• Synthetic studies towards (±)-phthalascidin 650: synthesis of a fully functionalized N-protected-α-amino-aldehyde
  作者：Sylvain Aubry、Christian R. Razafindrabe、Benjamin Bourdon、Stéphane Pellet-Rostaing、Marc Lemaire

  DOI：10.1016/j.tetlet.2007.10.111

  日期：2007.12

  An efficient synthesis of fully functionalized N-protected alpha-amino-aldehyde (+/-)-13 as synthetic precursor of the tetra-hydroisoquinoline alkaloid phthalascidin 650 is reported. Starting from sesamol 6, 11 steps are required to give rise to the desired N-protected alpha-amino-aldehyde (+/-)-13 in 25% overall yield. This synthetic strategy involves the elaboration of fully functionalized aromatic aldehyde 7 and its transformation into an alpha-amino-alcohol through a Knoevenagel condensation. The phthalimidomethyl derivative (+/-)-11 was then synthesised from 8 by a Bischler-Napieralski reaction, a diastereoselective hydrogenation of the resultant dihydroisoquinoline and transformed into the corresponding N-protected alpha-amino-aldehyde (+/-)-13. (C) 2007 Elsevier Ltd. All rights reserved.