cis-1,2,3,4-tetrahydro-3-(4-nitrophenyl)-1-oxo-2-(4-tolyl)isoquinoline-4-carboxylic acid

• 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: cis-1,2,3,4-tetrahydro-3-(4-nitrophenyl)-1-oxo-2-(4-tolyl)isoquinoline-4-carboxylic acid
• 英文别名: cis-3-(4-nitrophenyl)-1-oxo-2-p-tolyl-1,2,3,4-tetrahydroisoquinoline-4-carboxylic acid；3-(4-nitrophenyl)-1-oxo-2-p-tolyl-1,2,3,4-tetrahydro-isoquinoline-4-carboxylic acid；(3S,4R)-2-(4-methylphenyl)-3-(4-nitrophenyl)-1-oxo-3,4-dihydroisoquinoline-4-carboxylic acid
• 化学式: C₂₃H₁₈N₂O₅
• 分子量: 402.406
• InChiKey: KCOUGRAWYMIVBW-NHCUHLMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-(4-nitrobenzylidene)-4-methylaniline 、 高邻苯二甲酸酐 在 potassium aluminum sulfate 作用下， 以 乙腈 为溶剂， 反应 7.0h， 以86%的产率得到cis-1,2,3,4-tetrahydro-3-(4-nitrophenyl)-1-oxo-2-(4-tolyl)isoquinoline-4-carboxylic acid
  参考文献：
  名称：

  KAl(SO4)2·12H2O: An Efficient Catalyst for the Stereoselective Synthesis of cis- Isoquinolonic Acids

  摘要：

  KAl(SO4)(2).12H(2)O is found to catalyze efficiently the stereoselective cyclocondensation of homophthlic anhydride with imines under mild conditions to afford the corresponding cis-isoquinolonic acids in good yields.

  DOI：

  10.3987/com-04-10121

文献信息

• Iodine as a Mild, Efficient, and Cost-Effective Reagent for the Synthesis of <i>cis</i>-1-Oxo-1,2,3,4-tetrahydroisoquinoline-4-carboxylic Acids
  作者：J. Yadav、B. Reddy、A. Reddy、A. Narsaiah

  DOI：10.1055/s-2007-983899

  日期：2007.10

  Arylimines generated in situ from aromatic aldehydes and anilines undergo smooth coupling with homophthalic anhydride in the presence of 10 mol% of molecular iodine under mild and neutral conditions to afford the corresponding cis-1-oxo-1,2,3,4-tetrahydroisoquinoline-4-carboxylic acids in excellent yields with high cis selectivity. The use of iodine makes this procedure simple, convenient, and cost-effective.

  由芳香醛和苯胺原位生成的芳基亚胺在 10 摩尔分子碘存在下，在温和中性条件下与均苯二甲酸酐发生顺利偶联，从而得到相应的顺式-1-氧代-1,2,3,4-四氢异喹啉-4-羧酸，产量极佳，顺式选择性高。碘的使用使这一过程变得简单、方便和具有成本效益。
• A Stereoselective Three-Component Reaction:  KAl(SO₄)₂·12H₂O, an Efficient and Reusable Catalyst for the One-Pot Synthesis of <i>cis-</i>Isoquinolonic Acids
  作者：Javad Azizian、Ali A. Mohammadi、Ali R. Karimi、Mohammad R. Mohammadizadeh

  DOI：10.1021/jo049138g

  日期：2005.1.1

  KAl(SO4)2·12H2O is found to catalyze efficiently the stereoselective one-pot three-component cyclocondensation of homophthalic anhydride, aldehydes, and amines under mild conditions to afford the corresponding cis-isoquinolonic acids in good yields.

  发现KAl（SO 4）2 ·12H 2 O在温和条件下能有效催化高选择性的邻苯二甲酸，醛和胺的立体选择性一锅三组分环缩合反应，从而以良好的收率提供相应的顺式-异喹啉酸。
• A stereoselective three-component reaction: One-pot synthesis of<i>cis</i>-isoquinolonic acids catalyzed by silica sulfuric acid under mild and heterogeneous conditions
  作者：Javad Azizian、Ali A. Mohammadi、Ebrahim Soleimani、Ali R. Karimi、Mohammad R. Mohammadizadeh

  DOI：10.1002/jhet.5570430129

  日期：2006.1

  A mild and stereoselective three-component one-step synthesis of cis-isoquinolonic acid using silica sulfuric acid as a heterogeneous catalyst from an aldehyde, amine and homophthalic anhydride in acetonitrile is described. This new method produces pure products in high yields (81-91%).

  描述了一种温和且立体选择性的三组分一步法合成顺式-异喹啉酸，该反应使用二氧化硅硫酸作为乙腈中的醛，胺和高邻苯二甲酸酐作为多相催化剂。这种新方法可以高收率（81-91％）生产纯净的产品。
• Sulfonic Acid Functionalized Silica: A Mild, Reusable and Efficient Heterogeneous Catalyst for the Highly Diastereoselective Synthesis of cis-Isoquinolonic Acids
  作者：Ali Karimi、Rahim Pashazadeh

  DOI：10.1055/s-0029-1218595

  日期：2010.2

  Sulfonic acid functionalized silica (SAFS) is found to be a recyclable heterogeneous catalyst for the rapid and efficient synthesis of various cis-isoquinolonic acids from the three-component condensation reaction of homophthalic anhydride, an amine, and an aldehyde. This reaction was highly diastereoselective and only one diastereomer was obtained in all cases. sulfonic acid functionalized silica -

  磺酸官能化的二氧化硅（SAFS）被发现是可回收的非均相催化剂，用于由高邻苯二甲酸酐，胺和醛的三组分缩合反应快速有效地合成各种顺式-异喹啉酸。该反应是高度非对映选择性的，在所有情况下仅获得一种非对映异构体。 磺酸官能化二氧化硅-顺式-异喹啉酸-非对映选择性合成-三组分反应