3-(naphthalen-2-yl)isoquinolin-1(2H)-one

• 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: 3-(naphthalen-2-yl)isoquinolin-1(2H)-one
• 英文别名: 3-naphthalen-2-yl-2H-isoquinolin-1-one
• 化学式: C₁₉H₁₃NO
• 分子量: 271.318
• InChiKey: NFLDHBCVPMWMLO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(naphthalen-2-yl)isoquinolin-1(2H)-one 、 碳酸亚乙烯酯 在 tris(acetonitrile)(η5-pentamethylcyclopentadienyl)rhodium(III) hexafluoroantimonate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 以58%的产率得到
  参考文献：
  名称：

  碳酸亚乙烯酯作为氧化乙炔代用品的铑催化环偶联反应

  摘要：

  过渡金属催化的C–H活化以及随后的炔烃氧化环化反应一直是合成多环芳族化合物的有力工具。尽管在该领域取得了很大的进步，但是建立用于构建非取代的亚乙烯基稠合芳族化合物的合成方法学仍然是一个巨大的挑战。我们在此报告了用碳酸亚乙烯酯作为乙炔替代物的Rh（III）催化的CH / NH环合反应。碳酸亚乙烯酯还用作内部氧化剂，可在原位再生Rh（III）物种。因此，不需要外部氧化剂即可触发氧化环化反应。该协议适用于各种N-杂芳族化合物的直接合成。

  DOI：

  10.1021/acscatal.9b04254
• 作为产物：
  描述：

  N-(pivaloyloxy)benzamide 在 2-双环己基膦-2',6'-二甲氧基联苯 、 potassium phosphate 、 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 copper diacetate 、 palladium diacetate 、 cesium pivalate 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 22.0h， 生成 3-(naphthalen-2-yl)isoquinolin-1(2H)-one
  参考文献：
  名称：

  Mild Rh(III)-Catalyzed C–H Activation and Annulation with Alkyne MIDA Boronates: Short, Efficient Synthesis of Heterocyclic Boronic Acid Derivatives

  摘要：

  Taking advantage of Rh(III)-catalyzed C-H activation reactions, we have developed a mild, short, and efficient method for the synthesis of bench-stable 3-isoquinolone MIDA boronates. The reaction is practical and scalable. The product formed has been applied in the Suzuki-Miyaura reaction with high efficiency. This strategy has also been successfully expanded to the synthesis of MIDA boronate functionalized heterocycles such as isoquinoline, pyrrole, and indole.

  DOI：

  10.1021/ja310153v

文献信息

• Isoquinolone Synthesis through S_NAr Reaction of 2-Halobenzonitriles with Ketones Followed by Cyclization
  作者：Muhammad Shareef Mayo、Xiaoqiang Yu、Xiujuan Feng、Yoshinori Yamamoto、Ming Bao

  DOI：10.1021/acs.joc.5b00357

  日期：2015.4.17

  An efficient method for the synthesis of isoquinolones through base KOtBu-promoted SNAr reaction of 2-halobenzonitriles with ketones followed by Lewis acid Cu(OAc)2-catalyzed cyclization is described. Isoquinolone derivatives were obtained in satisfactory to good yields.

  描述了一种有效的方法，该方法通过2-卤代苄腈与酮的碱式KO t Bu促进的S N Ar反应，然后由路易斯酸Cu（OAc）2催化的环化来合成异喹诺酮。以令人满意的至良好的产率获得了异喹诺酮衍生物。
• Nickel‐Catalyzed Tandem Reaction of Functionalized Arylacetonitriles with Arylboronic Acids in 2‐MeTHF: Eco‐Friendly Synthesis of Aminoisoquinolines and Isoquinolones
  作者：Qianqian Zhen、Lepeng Chen、Linjun Qi、Kun Hu、Yinlin Shao、Renhao Li、Jiuxi Chen

  DOI：10.1002/asia.201901442

  日期：2020.1.2

  example of the nickel-catalyzed tandem addition/cyclization of 2-(cyanomethyl)benzonitriles with arylboronic acids in 2-MeTHF has been developed, which provides the facile synthesis of aminoisoquinolines with good functional group tolerance under mild conditions. This chemistry has also been successfully applied to the synthesis of isoquinolones by the tandem reaction of methyl 2-(cyanomethyl)benzoates

  已经开发了在2-MeTHF中镍催化的芳基硼酸串联（2-（氰基甲基）苄腈串联/加成环的第一个例子），该化合物在温和条件下可轻松合成具有良好官能团耐受性的氨基异喹啉。通过2-（氰基甲基）苯甲酸甲酯与芳基硼酸的串联反应，该化学方法也已成功地用于异喹诺酮的合成。使用生物基和绿色溶剂2-MeTHF作为反应介质使合成过程在环境方面无害。这种化学的合成效用还通过生物活性分子的合成来表明。
• Iridium-catalyzed oxidative coupling and cyclization of NH isoquinolones with olefins leading to isoindolo[2,1-b]isoquinolin-5(7H)-one derivatives
  作者：Kelu Yan、Xiao Liu、Min Liu、Jiangwei Wen、Mingyue Du、Yingxue Fu、Wenxin Chen

  DOI：10.1016/j.tetlet.2022.153779

  日期：2022.5

  coupling and cyclization of NH isoquinolones with olefins has been realized. Most isoindolo[2,1-b]isoquinolin-5(7H)-one derivatives were obtained in moderate to good yields. Several derivatization reactions including functional group conversion and further CH/olefin coupling were also performed. This transformation realized the less developed Cp*Ir(III) catalyzed coupling and cyclization reaction of

  已经实现了铱催化的NH异喹诺酮与烯烃的氧化偶联和环化。大多数异吲哚[2,1- b ]isoquinolin-5(7H)-one 衍生物以中等至良好的产率获得。还进行了几个衍生反应，包括官能团转化和进一步的 C H /烯烃偶联。这种转化实现了较少开发的 Cp*Ir(III) 催化的 NH 底物与烯烃的偶联和环化反应。
• One-Pot Synthesis of 3-Substituted Isoquinolin-1-(2H)-ones and Fused Isoquinolin-1-(2H)-ones by SRN1 Reactions in DMSO
  作者：Javier F. Guastavino、Silvia M. Barolo、Roberto A. Rossi

  DOI：10.1002/ejoc.200600244

  日期：2006.9

  3-Substituted isoquinolin-1-(2H)-ones and fused isoquinolin-1-(2H)-ones have been obtained by the photostimulated SRN1 reactions of 2-iodobenzamide with the enolates of aromatic (acetophenone, 1-(benzo[d][1,3]dioxol-5-yl)ethanone, 1- and 2-naphthyl methyl ketones, and 2-, 3-, and 4-acetylpyridine), aliphatic (1-adamantyl methyl ketone), and cyclic ketones (1- and 2-indanone, α- and β-tetralone, and

  3-取代的异喹啉-1-(2H)-酮和稠合的异喹啉-1-(2H)-酮是通过 2-碘苯甲酰胺与芳香族（苯乙酮，1-（苯并[d]）的烯醇化物的光刺激 SRN1 反应获得的[1,3]dioxol-5-yl)ethanone, 1- and 2-naphthylmethyl ketones, and 2-, 3-, and 4-acetylpyridine), 脂肪族（1-adamantylmethyl ketone）和环酮（1-和 2-茚满酮、α-和β-四氢萘酮以及 1-苯并芴酮）在 DMSO 中。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
• Tandem Addition/Cyclization for Access to Isoquinolines and Isoquinolones via Catalytic Carbopalladation of Nitriles
  作者：Linjun Qi、Kun Hu、Shuling Yu、Jianghe Zhu、Tianxing Cheng、Xiaodong Wang、Jiuxi Chen、Huayue Wu

  DOI：10.1021/acs.orglett.6b03499

  日期：2017.1.6

  sequential nucleophilic addition followed by an intramolecular cyclization of functionalized nitriles with arylboronic acids has been achieved, providing an efficient synthetic pathway to access structurally diverse isoquinolines and isoquinolones. This methodology has also been successfully applied to the total synthesis of the topoisomerase I inhibitor CWJ-a-5 (free base).

  已经实现了钯催化的连续亲核加成，然后用芳基硼酸进行分子内官能化腈分子内环化的第一个例子，从而提供了一种有效的合成途径，以获取结构多样的异喹啉和异喹啉酮。该方法也已成功应用于拓扑异构酶I抑制剂CWJ-a-5（游离碱）的全合成。