2-cyclohexyl-3-phenylisoquinolin-1(2H)-one | 1367766-62-8

• 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: 2-cyclohexyl-3-phenylisoquinolin-1(2H)-one
• 英文别名: 2-Cyclohexyl-3-phenylisoquinolin-1-one；2-cyclohexyl-3-phenylisoquinolin-1-one
• CAS: 1367766-62-8
• 化学式: C₂₁H₂₁NO
• 分子量: 303.404
• InChiKey: XROFKVMXCDIFPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  1-溴-2-(2,2-二溴乙烯基)苯 在 tris-(dibenzylideneacetone)dipalladium(0) 、 三(2-呋喃基)膦 、 caesium carbonate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 、 sodium t-butanolate 作用下， 以 1,4-二氧六环 、 水 、 甲苯 为溶剂， 55.0~90.0 ℃ 、101.33 kPa 条件下， 反应 35.0h， 生成 2-cyclohexyl-3-phenylisoquinolin-1(2H)-one
  参考文献：
  名称：

  A new access to 3-substituted-1(2H)-isoquinolone by tandem palladium-catalyzed intramolecular aminocarbonylation annulation

  摘要：

  报道了一种基于三溴衍生物的钯催化合成3-取代-1(2H)-异喹啉酮的方法，该方法基于在邻卤-(2,2-二卤乙烯基)-苯上选择性Suzuki-宫浦C-C偶联反应，然后通过钯催化的氨基化-羰基化-环合反应实现。该反应序列通过一次三键合成反应高效地构建异喹啉酮，产率中等至良好。

  DOI：

  10.1039/c2ob06852d

文献信息

• Nickel‐Catalyzed Annulation of <i>o</i> ‐Haloarylamidines with Aryl Acetylenes: Synthesis of Isoquinolone and 1‐Aminoisoquinoline Derivatives
  作者：Hao Xie、Qiaoyan Xing、Zhifei Shan、Fuhong Xiao、Guo‐Jun Deng

  DOI：10.1002/adsc.201801635

  日期：2019.4.16

  An efficient method for the synthesis of substituted 1(2H)‐isoquinolone derivatives via nickel‐catalyzed annulation of substituted 2‐halobenzamidines with aryl alkynes in the presence of water is described. Benzo[4,5]imidazo[2,1‐a]isoquinolines were formed as the dominated products when dry dimethyl sulfoxide was used as the solvent. Furthermore, when benzyl substituted amidines were used as the substrates

  描述了一种在水存在下，通过镍催化的芳基炔烃与取代的2-卤代苯甲an的环合反应，合成取代的1（2 H）-异喹诺酮衍生物的有效方法。苯并[4,5]咪唑并[2,1-一个当干二甲亚砜作为溶剂]异喹啉被形成为主导的产品。此外，当使用苄基取代的idine作为底物时，发生脱苄基反应以提供各种1-氨基异喹啉产物。
• Solvent-Switched Benzylic Methylene Functionalization: Addition, Ring-Opening, Cyclization, and Unexpected Cleavage of C–O and C–C Bonds
  作者：Deng Yuan Li、Xue Song Shang、Guo Rong Chen、Pei Nian Liu

  DOI：10.1021/ol401470y

  日期：2013.8.2

  been achieved using imines as reagents and potassium tert-butoxide as the catalyst. Depending on the solvent used, the reaction proceeds by two pathways. In THF, an addition/elimination reaction of exo-cyclic enol ethers with imines provides dihydroisobenzofuran derivatives in good yield. In DMSO, an addition/ring-opening/cyclization cascade reaction occurs with unexpected cleavage of C–O and C–C bonds

  使用亚胺作为试剂并使用叔丁醇钾作为催化剂，可以实现环外烯醇醚的分子间苄基亚甲基官能化。根据所使用的溶剂，反应通过两个途径进行。在THF中，的加成/消除反应外切-环烯醇醚与亚胺提供以良好的收率二氢异苯并呋喃衍生物。在DMSO中，加成/开环/环化级联反应会发生意外的C–O和C–C键断裂，从而在环境反应条件下以高收率提供异喹啉-1（2 H）-一产品。
• Transition Metal-Free Cascade Reactions of Alkynols to Afford Isoquinolin-1(2<i>H</i>)-one and Dihydroisobenzofuran Derivatives
  作者：Deng Yuan Li、Ke Ji Shi、Xiao Feng Mao、Guo Rong Chen、Pei Nian Liu

  DOI：10.1021/jo5006312

  日期：2014.5.16

  Transition metal-free cascade reactions of alkynols with imines have been achieved using potassium tert-butoxide as catalyst. Switching the reaction solvent gives two kinds of products in good yield: isoquinolin-1(2H)-one derivatives and dihydroisobenzofuran derivatives. This approach was used to generate the natural product 8-oxypseudopalmatine in a two-step procedure from commercially available starting materials. Additionally, multicomponent reactions of alkynols, aldehydes, and amines were also successfully achieved to afford isoquinolin-1(2H)-one derivatives.
• A new access to 3-substituted-1(2H)-isoquinolone by tandem palladium-catalyzed intramolecular aminocarbonylation annulation
  作者：Antoine Dieudonné-Vatran、Michel Azoulay、Jean-Claude Florent

  DOI：10.1039/c2ob06852d

  日期：——

  An original tribromide derivative based, palladium-catalyzed synthesis of 3-substituted-1(2H)-isoquinolone is described based on a regioselective Suzuki–Miyaura C–C coupling on o-halo-(2,2-dihalovinyl)-benzene followed by a palladium catalyzed amination–carbonylation–cyclization reaction. This sequence efficiently proceeds to build up isoquinolone in fair to good yields over a one-pot 3-bond synthesis reaction.

  报道了一种基于三溴衍生物的钯催化合成3-取代-1(2H)-异喹啉酮的方法，该方法基于在邻卤-(2,2-二卤乙烯基)-苯上选择性Suzuki-宫浦C-C偶联反应，然后通过钯催化的氨基化-羰基化-环合反应实现。该反应序列通过一次三键合成反应高效地构建异喹啉酮，产率中等至良好。