3,4-diethylisoquinolin-1(2H)-one | 1246278-82-9

• 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: 3,4-diethylisoquinolin-1(2H)-one
• 英文别名: 3,4-diethyl-2H-isoquinolin-1-one
• CAS: 1246278-82-9
• 化学式: C₁₃H₁₅NO
• 分子量: 201.268
• InChiKey: JNAZPAFEIGEMJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  3,4-diethylisoquinolin-1(2H)-one 、 盐酸氨基脲 以 乙醇 、 水 为溶剂， 反应 3.0h， 以60%的产率得到3,4-diethylisoquinoline semicarbazone
  参考文献：
  名称：

  Rai; Sharma, Oriental Journal of Chemistry, 2011, vol. 27, # 1, p. 143 - 148

  摘要：

  DOI：
• 作为产物：
  描述：

  2-碘苯甲酰胺 以 二氯甲烷 、 丙酮 为溶剂， 反应 26.0h， 生成 3,4-diethylisoquinolin-1(2H)-one
  参考文献：
  名称：

  Reactivity of Ortho-Palladated Benzamides toward CO, Isocyanides, and Alkynes. Synthesis of Functionalized Isoindolin-1-ones and 4,5-Disubstituted Benzo[c]azepine-1,3-diones

  摘要：

  Aryl palladium complexes [Pd{C6H4C(O)NRR'-2}I(tmeda)] [NRR' = NH2 (1a), NHMe (1b), NMe2 (1c); tmeda = N,N,N',N'-tetramethylethylenediamine] are prepared by oxidative addition of the corresponding 2-iodophenylbenzamides to Pd(dba)(2) ([Pd-2(dba)(3)]center dot dba; dba = dibenzylideneacetone) in the presence of tmeda. Cationic cyclometalated derivatives [Pd{'2C,O-C6H4C(O)NRR'-2}(tmeda)]TfO (2ac) are obtained by iodide abstraction from the appropriate complex 1 with AgTfO, while the deprotonation of the amide function of 1a or 1b with KOtBu gives the neutral amidate complexes [Pd{'2C,N-C6H4C(O)NR-2}(tmeda)] [R = H (3a), Me (3b)]. Complexes 2a,b and 3a,b react with CO under mild conditions to yield phthalimide (4a) or N-methylphthalimide (4b), whereas the reactions of derivatives 1c and 2c with CO are very slow and give N-1,N-1,N-2,N-2-tetramethylphthalamide and phthalic anhydride. The reaction of 1b with 1 equiv of XyNC (Xy = 2,6-dimethylphenyl) or tBuNC affords Pd(0), (tmedaH)I, and 3-(2,6-dimethylphenylimino)-2-methylisoindolin-1-one (5b) or 3-(tert-butylimino)-2-methylisoindolin-1-one (5b'), respectively, while complex 1c reacts with 3 equiv of XyNC to give trans-[Pd{C('NXy)C6H4C(O)NMe2-2}I(CNXy)(2)] (6). The seven-membered palladacycles [Pd{'2C,O-C(X)'C(X')C6H4C(O)NRR'-2}(tmeda)]TfO [NRR' = NH2 and X = Ph, X' = Me (7a); NRR' = NHMe and X = Ph, X' = Me (7b), X = X' = Ph (8b), Et (9b), CO2Me (10b), X = CO2Me, X' = Ph (11b), X = CO2Et, X' = Ph (12b); NRR' = NMe2 and X = X' = Ph (8c), Et (9c)] are obtained from the reactions of 2ac with alkynes. Treatment of complexes 7a, 7b, 8b, and 9b with CO at room temperature gives the corresponding 2H-benzo[c]azepine-1,3-diones (14), resulting from the insertion of a molecule of CO into the PdC bond followed by a CN reductive coupling. In contrast, the reactions of 11b or 12b with CO in the presence of residual water or 2 equiv of ROH (R = Me, Et) lead to 2-methyl-3-phenylisoindolin-1-one derivatives (15), resulting from a CO insertion followed by an intramolecular aza-Michael addition of the NHMe moiety to the activated vinyl group and subsequent hydrolysis or alcoholysis of the acylPd bond. The neutral complex [Pd('2C,O-C14H13O5)(tmeda)] (18) was synthesized by reacting the cationic derivative 10b with NaOMe in MeOH. Depalladation of 18 gives (E)-4-[methoxy(methoxycarbonyl)methylene]-2-methylisoquinoline-1,3(2H,4H)-dione (19).

  DOI：

  10.1021/om4006406

文献信息

• Ruthenium-Catalyzed Isoquinolone Synthesis through CH Activation Using an Oxidizing Directing Group
  作者：Bin Li、Huiliang Feng、Shansheng Xu、Baiquan Wang

  DOI：10.1002/chem.201102445

  日期：2011.11.4

  The oxidant directs: A mild, practical, efficient, and regioselective Ru‐catalyzed isoquinolone synthesis with a broad substrate scope was reported (see scheme). In this redox neutral process, the aromatic CH bond functionalization can be performed at room temperature without using any external oxidant. The mechanism of the reaction was probed, and it was found that CH activation is the turnover‐limiting

  氧化剂的方向：据报道，该方法温和，实用，有效且具有区域选择性，Ru催化的异喹诺酮合成具有广泛的底物范围（参见方案）。在这种氧化还原中性工艺中，可以在室温下进行芳族CH键官能化，而无需使用任何外部氧化剂。探究了反应的机理，发现CH活化是限制周转的步骤。
• 一种医药中间体异喹啉酮化合物的制备方法
  申请人：周晓芳

  公开号：CN106977455A

  公开（公告）日：2017-07-25

  本发明涉及一种取代的异喹啉酮化合物的制备方法，包括以下步骤：在催化剂和碱的存在下，取代的苯甲酰胺化合物与取代炔烃化合物在反应溶剂中反应，得到取代异喹啉酮化合物，该方法产率高、合成路线短、条件温和、操作简单，具有良好的应用前景和工业化生产潜力。
• Palladium‐Catalyzed Inert C−H Bond Activation and Cyclocarbonylation of Isoquinolones with Carbon Dioxide Leading to Isoindolo[2,1‐ <i>b</i> ]isoquinoline‐5,7‐Diones
  作者：Kelu Yan、Junbin Jin、Yong Kong、Bin Li、Baiquan Wang

  DOI：10.1002/adsc.201900305

  日期：2019.7.2

  A palladium‐catalyzed inert C−H bond activation and cyclocarbonylation of isoquinolones leading to isoindolo[2,1‐b]isoquinoline‐5,7‐diones under 1 atm of carbon dioxide has been developed. This transformation features high regio‐ and chemo‐selectivity, step‐economy, and good functional group tolerance. Most of the corresponding products were obtained in moderate to good yields. It offers an alternative

  已开发出在1个大气压的二氧化碳下，钯催化的惰性C-H键活化和异喹诺酮的环羰基化反应，导致异吲哚并[2,1 – b ]异喹啉-5,7-二酮。这种转变具有很高的区域选择性和化学选择性，逐步经济性和良好的官能团耐受性。大部分相应的产品以中等到良好的产率获得。它为合成有用的多种异吲哚并[2,1 - b ]异喹啉-5,7-二酮衍生物提供了另一种方法。
• Rhodium-catalyzed C–H activation of hydrazines leads to isoquinolones with tunable aggregation-induced emission properties
  作者：Bole Yu、Ying Chen、Mei Hong、Pingping Duan、Shifeng Gan、Hui Chao、Zujin Zhao、Jing Zhao

  DOI：10.1039/c5cc05239d

  日期：——

  We report a Rh^III-catalyzed synthesis of isoquinolonesviaC–H activation/annulation of benzoylhydrazines and alkynes for AIE studies.

  我们报道了一种Rh^III催化的合成方法，通过苯甲酰肼和炔烃的C-H活化/环化反应合成异喹啉，用于AIE研究。
• Rapid and Atom Economic Synthesis of Isoquinolines and Isoquinolinones by C-H/N-N Activation Using a Homogeneous Recyclable Ruthenium Catalyst in PEG Media
  作者：Dewal S. Deshmukh、Neha Gangwar、Bhalchandra M. Bhanage

  DOI：10.1002/ejoc.201900366

  日期：2019.5.15

  An atom‐efficient, rapid, green and sustainable approach has been developed for the synthesis of isoquinolines and isoquinolinones by annulation via C–H/N–N activation using a homogeneous recyclable ruthenium catalyst in PEG media.

  已经开发了一种原子高效，快速，绿色且可持续的方法，用于在PEG介质中使用均相可回收钌催化剂通过C–H / N–N活化进行环化来合成异喹啉和异喹啉酮。