4-ethyl-2-methyl-3-phenylisoquinolin-1(2H)-one | 1235479-12-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4-ethyl-2-methyl-3-phenylisoquinolin-1(2H)-one
• 英文别名: 4-Ethyl-2-methyl-3-phenylisoquinolin-1-one；4-ethyl-2-methyl-3-phenylisoquinolin-1-one
• CAS: 1235479-12-5
• 化学式: C₁₈H₁₇NO
• 分子量: 263.339
• InChiKey: OWCMAGXKSORMMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  N-甲基苯甲酰胺 、 1-苯基-1-丁炔 在 [Cp*Rh(CH₃CN)₃](BF₄)₂ 、 potassium carbonate 作用下， 以 水 为溶剂， 110.0 ℃ 、101.33 kPa 条件下， 反应 16.0h， 生成 4-ethyl-2-methyl-3-phenylisoquinolin-1(2H)-one
  参考文献：
  名称：

  空气作为水中唯一的氧化剂，通过Rh催化的取代苯甲酰胺的C–H活化，合成异喹诺酮

  摘要：

  大多数金属催化的C–H活化/环化反应都是在有机溶剂中使用昂贵的氧化剂，例如Cu（II）和Ag（I）盐进行的。在这里，我们报道了一种新方法，可在水介质中使用Rh（III）催化剂和廉价的氧气作为唯一氧化剂，从N-烷基苯甲酰胺和炔烃高度区域选择性合成异喹诺酮。在反应中，水在所用溶剂中的产率最高。另外，在反应结束时，异喹诺酮产物直接从水溶液中沉淀出来。该方法可以应用于克级合成。Rh（III）催化的反应显示出有趣的间位与间位取代的苯甲酰胺具有选择性，并显示出不同取代的炔烃的各种区域选择性。而且，该方法可以用于制备具有异喹诺酮核心的生物活性化合物。

  DOI：

  10.1039/c7gc01221g

文献信息

• Synthesis of Highly Substituted Isoquinolone Derivatives by Nickel-Catalyzed Annulation of 2-Halobenzamides with Alkynes
  作者：Chuan-Che Liu、Kanniyappan Parthasarathy、Chien-Hong Cheng

  DOI：10.1021/ol101371c

  日期：2010.8.6

  An efficient method for the synthesis of substituted 1(2H)-isoquinolone derivatives via nickel-catalyzed annulation of substituted 2-halobenzamides with alkynes is described. This protocol is successfully applied to the total synthesis of oxyavicine with excellent yield.

  描述了一种通过镍催化的炔基与取代的2-卤代苯甲酰胺环合反应合成取代的1（2 H）-异喹诺酮衍生物的有效方法。该方案已成功地以优异的收率应用于羟乙胺嘧啶的全合成。
• Synthesis of isoquinolones via Rh-catalyzed C–H activation of substituted benzamides using air as the sole oxidant in water
  作者：Nitinkumar Satyadev Upadhyay、Vijaykumar H. Thorat、Ryota Sato、Pratheepkumar Annamalai、Shih-Ching Chuang、Chien-Hong Cheng

  DOI：10.1039/c7gc01221g

  日期：——

  metal-catalyzed C–H activation/annulation reactions were carried out in organic solvents using expensive oxidants such as Cu(II) and Ag(I) salts. Here, we reported a new approach for a highly regioselective synthesis of isoquinolones from N-alkyl benzamides and alkynes using an Rh(III) catalyst and inexpensive oxygen as the sole oxidant in an aqueous medium. In the reaction, water gave the highest product yield

  大多数金属催化的C–H活化/环化反应都是在有机溶剂中使用昂贵的氧化剂，例如Cu（II）和Ag（I）盐进行的。在这里，我们报道了一种新方法，可在水介质中使用Rh（III）催化剂和廉价的氧气作为唯一氧化剂，从N-烷基苯甲酰胺和炔烃高度区域选择性合成异喹诺酮。在反应中，水在所用溶剂中的产率最高。另外，在反应结束时，异喹诺酮产物直接从水溶液中沉淀出来。该方法可以应用于克级合成。Rh（III）催化的反应显示出有趣的间位与间位取代的苯甲酰胺具有选择性，并显示出不同取代的炔烃的各种区域选择性。而且，该方法可以用于制备具有异喹诺酮核心的生物活性化合物。
• Synthesis of N-alkyl and N-aryl isoquinolones and derivatives via Pd-catalysed C–H activation and cyclization reactions
  作者：Nana Zhang、Binyao Li、Hongban Zhong、Jianhui Huang

  DOI：10.1039/c2ob26668g

  日期：——

  Relatively less expensive Pd-catalysed oxidative coupling reactions for the preparation of N-alkyl and N-aryl substituted isoquinolones and their derivatives have been developed. A broad reaction scope has been demonstrated. In addition, studies of the reaction additives and mechanistic insights, as well as KIE studies for a better understanding of the reaction pathway, have been discussed.

  已经开发了用于制备N-烷基和N-芳基取代的异喹诺酮及其衍生物的相对便宜的Pd催化的氧化偶联反应。已经证明了广泛的反应范围。此外，还讨论了对反应添加剂和机理的研究，以及为了更好地了解反应途径而进行的KIE研究。
• Rhodium-Catalyzed Oxidative Cycloaddition of Benzamides and Alkynes via C−H/N−H Activation
  作者：Todd K. Hyster、Tomislav Rovis

  DOI：10.1021/ja103776u

  日期：2010.8.4

  The oxidative cycloaddition of benzamides and alkynes has been developed. The reaction utilizes Rh(III) catalysts in the presence of Cu(II) oxidants, and is proposed to proceed by N-H metalation of the amide followed by ortho C-H activation. The resultant rhodacycle undergoes alkyne insertion to form isoquinolones in good yield. The reaction is tolerant of extensive substitution on the amide, alkyne, and arene, including halides, silyl ethers, and unprotected aldehydes as substituents. Unsymmetrical alkynes proceed with excellent regioselectivity, and heteroaryl carboxamides are tolerated leading to intriguing scaffolds for medicinal chemistry. A series of competition experiments shed further light on the mechanism of the transformation and reasons for selectivity.
• Pd/C-catalyzed synthesis of N -aryl and N -alkyl isoquinolones via C H/N H activation
  作者：Zhen Shu、Yuntao Guo、Wei Li、Baiquan Wang

  DOI：10.1016/j.cattod.2017.02.005

  日期：2017.11

  Pd/C-catalyzed direct synthesis of N-aryl and N-alkyl isoquinolones was developed via the annulation reactions of benzamides and alkynes in high yields (up to 99%) through the cleavage of CH/NH bonds. The reaction was ligand-free and air was used as oxidant. High regioselectivities were found when unsymmetrical alkynes or meta-benzamides were used as substrates. The heterocyclic carboxamide substrates

  通过苯甲酰胺和炔烃的环化反应，通过C H / N H键的裂解，Pd / C催化直接合成N-芳基和N-烷基异喹诺酮。该反应不含配体，将空气用作氧化剂。当使用不对称炔烃或间苯甲酰胺作为底物时，具有较高的区域选择性。杂环羧酰胺底物，例如呋喃和噻吩衍生物，也以高收率提供了相应的产物。