cis-2-(4-methylphenyl)-1-oxo-3-phenyl-1,2,3,4-tetrahydro-4-isoquinoline-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-2-(4-methylphenyl)-1-oxo-3-phenyl-1,2,3,4-tetrahydro-4-isoquinoline-carboxylic acid
• 英文别名: 2-(4-methylphenyl)-1-oxo-3-phenyl-1,2,3,4-tetrahydro-4-isoquinoline-carboxylic acid；cis-1,2,3,4-tetrahydro-1-oxo-3-phenyl-2-(4-tolyl)isoquinoline-4-carboxylic acid；cis-1-oxo-3-phenyl-2-p-tolyl-1,2,3,4-tetrahydroisoquinoline-4-carboxylic acid；1-oxo-3-phenyl-2-p-tolyl-1,2,3,4-tetrahydro-isoquinoline-4-carboxylic acid；(3S,4R)-2-(4-methylphenyl)-1-oxo-3-phenyl-3,4-dihydroisoquinoline-4-carboxylic acid
• 化学式: C₂₃H₁₉NO₃
• 分子量: 357.409
• InChiKey: CDVBBRBSRNVKAB-NHCUHLMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  27
• 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：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  高邻苯二甲酸酐 、 N亚苄基对甲苯胺 在 potassium aluminum sulfate 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以90%的产率得到cis-2-(4-methylphenyl)-1-oxo-3-phenyl-1,2,3,4-tetrahydro-4-isoquinoline-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。
• Room temperature ionic liquids promoted three-component coupling reactions: a facile synthesis of cis-isoquinolonic acids
  作者：J.S Yadav、B.V.S Reddy、K Saritha Raj、A.R Prasad

  DOI：10.1016/s0040-4020(03)00076-0

  日期：2003.3

  Room temperature ionic liquids are found to catalyze efficiently the three component-coupling reactions of aldehydes, amines and homophthalic anhydride under mild and convenient conditions to afford the corresponding cis-isoquinolonic acids in excellent yields with high cis-selectivity.

  发现室温离子液体在温和且方便的条件下有效催化醛，胺和高苯酐的三组分偶联反应，以高收率和高顺式选择性提供相应的顺式-异喹啉酸。
• One-Pot Synthesis ofcis-Isoquinolonic Acid Derivativesvia Three-Component Reaction of Homophthalic Anhydride with Aldehydes and Amines using Ytterbium(III) Triflate as Catalyst
  作者：Limin Wang、Jijun Liu、He Tian、Changtao Qian、Jie Sun

  DOI：10.1002/adsc.200404211

  日期：2005.4

  Ytterbium(III) triflate efficiently catalyzes the one-pot reaction of homophthalic anhydride with aldehydes and amines at ambient temperature to afford the corresponding cis-isoquinolonic acid derivatives in good to excellent yields with high diastereoselectivity. This method provides a novel and much improved modification of the three-component reaction in terms of mild reaction conditions, short

  三氟甲磺酸（III）在环境温度下有效催化高邻苯二甲酸酐与醛和胺的一锅反应，从而以高至非对映异构体的收率很好地获得相应的顺式-异喹啉酸衍生物。该方法在温和的反应条件，短的反应时间，清洁的反应曲线，少量的催化剂和简单的后处理方面提供了新颖且大大改进的三组分反应的改进。该方法的另一个重要特征是反应后催化剂可以容易地从水层中回收，并且可以在不损失活性的情况下重复使用。