2,3-dimethoxy-12b-(2-oxopropyl)-5,12b-dihydro-6H-isoindolo[1,2-a]isoquinolin-8-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2,3-dimethoxy-12b-(2-oxopropyl)-5,12b-dihydro-6H-isoindolo[1,2-a]isoquinolin-8-one
• 英文别名: 2,3-Dimethoxy-12b-phenacyl-5,6-dihydroisoindolo[1,2-a]isoquinolin-8-one；2,3-dimethoxy-12b-phenacyl-5,6-dihydroisoindolo[1,2-a]isoquinolin-8-one
• 化学式: C₂₆H₂₃NO₄
• 分子量: 413.473
• InChiKey: XBLBZLHJIAMNJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-[2-(2-Iodo-4,5-dimethoxyphenyl)ethyl]isoindole-1,3-dione 在 正丁基锂 、 四氯化钛 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 2,3-dimethoxy-12b-(2-oxopropyl)-5,12b-dihydro-6H-isoindolo[1,2-a]isoquinolin-8-one
  参考文献：
  名称：

  Tandem Parham cyclisation––α-amidoalkylation reaction in the synthesis of the isoindolo[1,2- a ]isoquinoline skeleton of nuevamine-type alkaloids

  摘要：

  C-12b substituted isoindolo[1,2-a]isoquinolones 4 are prepared efficiently via a tandem Parham cyclisation-alpha-amidoalkylation reaction. Thus, Parham cyclisation on imide I generates a 12b-hydroxy isoindolo[1,2-a]isoquinolone, which is an immediate precursor of an N-acyliminium ion. Intermolecular alkylation with different pi-nucleophiles (allyl silanes or enol ethers) is accomplished upon treatment with Lewis acids (BF3.OEt2, TiCl4) to obtain nuevamine-type derivatives in high yields (69-95%) under mild conditions. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.11.122

文献信息

• Chiral Brønsted Acid-Catalyzed Enantioselective α-Amidoalkylation Reactions: A Joint Experimental and Predictive Study
  作者：Eider Aranzamendi、Sonia Arrasate、Nuria Sotomayor、Humberto González-Díaz、Esther Lete

  DOI：10.1002/open.201600120

  日期：2016.12

  Enamides with a free NH group have been evaluated as nucleophiles in chiral Brønsted acid‐catalyzed enantioselective α‐amidoalkylation reactions of bicyclic hydroxylactams for the generation of quaternary stereocenters. A quantitative structure–reactivity relationship (QSRR) method has been developed to find a useful tool to rationalize the enantioselectivity in this and related processes and to orient

  具有游离 NH 基团的烯酰胺已被评估为手性布朗斯台德酸催化的双环羟基内酰胺对映选择性 α-酰胺烷基化反应中的亲核试剂，用于生成四元立构中心。我们开发了一种定量结构-反应性关系（QSRR）方法，以找到一种有用的工具来合理化该过程及相关过程中的对映选择性，并确定催化剂的选择。这种相关微扰理论 (PT)-QSRR 方法已用于预测底物、亲核试剂和催化剂的结构以及实验条件对对映选择性的影响。这样，无需进行长期的实证研究，就可以发现改善实验结果的趋势。
• Tandem Parham cyclisation––α-amidoalkylation reaction in the synthesis of the isoindolo[1,2- a ]isoquinoline skeleton of nuevamine-type alkaloids
  作者：Iñaki Osante、Esther Lete、Nuria Sotomayor

  DOI：10.1016/j.tetlet.2003.11.122

  日期：2004.2

  C-12b substituted isoindolo[1,2-a]isoquinolones 4 are prepared efficiently via a tandem Parham cyclisation-alpha-amidoalkylation reaction. Thus, Parham cyclisation on imide I generates a 12b-hydroxy isoindolo[1,2-a]isoquinolone, which is an immediate precursor of an N-acyliminium ion. Intermolecular alkylation with different pi-nucleophiles (allyl silanes or enol ethers) is accomplished upon treatment with Lewis acids (BF3.OEt2, TiCl4) to obtain nuevamine-type derivatives in high yields (69-95%) under mild conditions. (C) 2003 Elsevier Ltd. All rights reserved.