3,4-bis(4-chlorophenyl)isoquinolin-1(2H)-one | 1312991-51-7

• 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: 3,4-bis(4-chlorophenyl)isoquinolin-1(2H)-one
• 英文别名: 3,4-bis(4-chlorophenyl)-2H-isoquinolin-1-one
• CAS: 1312991-51-7
• 化学式: C₂₁H₁₃Cl₂NO
• 分子量: 366.246
• InChiKey: BTTNMCJYLMBGPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.17
• 重原子数：
  25.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  32.86
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  丙烯酸苄酯 、 3,4-bis(4-chlorophenyl)isoquinolin-1(2H)-one 在 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 copper diacetate 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以88%的产率得到benzyl 2-[9-chloro-12-(4-chlorophenyl)-5-oxo-7H-isoindolo[2,1-b]isoquinolin-7-yl]acetate
  参考文献：
  名称：

  Oxidative Coupling of NH Isoquinolones with Olefins Catalyzed by Rh(III)

  摘要：

  Rh(III)-catalyzed oxidative coupling reactions between isoquinolones with 3-aryl groups and activated olefins have been achieved using anhydrous Cu(OAc)(2) as an oxidant to give tetracyclic products. The nitrogen atom acts as a directing group to facilitate ortho C-H activation. This reaction can be one-pot starting from methyl benzohydroxamates, without the necessity of the isolation of isoquinolone products. Abroad scope of substrates has been demonstrated, and both terminal and internal activated olefins can be applied. In the coupling of N-methylmaleimide, a Wacker-like mechanism was proposed, where backside attack of the NH group in isoquinolones is suggested as a key step. Selective C-H activation has also been achieved at the 8-position of 1-naphthol, leading to an olefination product.

  DOI：

  10.1021/jo2002209
• 作为产物：
  描述：

  苯甲酸 在 氯化亚砜 、 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 sodium acetate 、 一水合肼 、 三甲基乙酸 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 24.0h， 生成 3,4-bis(4-chlorophenyl)isoquinolin-1(2H)-one
  参考文献：
  名称：

  Rhodium-catalyzed C–H activation of hydrazines leads to isoquinolones with tunable aggregation-induced emission properties

  摘要：

  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。

  DOI：

  10.1039/c5cc05239d

文献信息

• Palladium-Catalyzed Oxidative Cyclocarbonylation of Isoquinolones with CO via C−H/N−H Bond Cleavage: Easy Access to Isoindolo[2,1-<i>b</i> ]isoquinoline-5,7-dione Derivatives
  作者：Shenghai Guo、Fang Wang、Lincong Sun、Xinying Zhang、Xuesen Fan

  DOI：10.1002/adsc.201800347

  日期：2018.7.4

  An efficient and practical synthesis of isoindolo[2,1‐b]isoquinoline‐5,7‐diones through Pd‐catalyzed C−H activation/carbonylative annulation of isoquinolones with CO (1 atm) is presented. Deuterium‐labeling experiments revealed that the aryl C(sp2)−H bond activation might be the rate‐determining step. More interestingly, the title compounds could also be prepared directly from the cascade reaction

  提出了一种通过Pd催化的CH活化/异喹啉酮与CO（1 atm）羰基环化反应有效合成异吲哚并[2,1 – b ]异喹啉-5,7-二酮的方法。氘标记实验表明，芳基C（sp 2）-H键的活化可能是决定速率的步骤。更有趣的是，标题化合物也可以直接由N-甲氧基苯甲酰胺和内部炔烃（作为异喹诺酮的前体）在一氧化碳的大气压下，通过Rh / Pd中继催化，以用户友好的方式级联反应制备。。
• Development of a Traceless Directing Group: Cp*-Free Cobalt-Catalyzed C–H Activation/Annulations to Access Isoquinolinones
  作者：Minghui Liu、Jun-Long Niu、Dandan Yang、Mao-Ping Song

  DOI：10.1021/acs.joc.9b03073

  日期：2020.3.20

  A new traceless directing group, 2-(hydroxymethyl)pyridine, has been reported for the Cp*-free cobalt-catalyzed C-H activation/annulation reaction to synthesize isoquinolinones. The reaction exhibits good functional group tolerance, affording products in good to excellent isolated yields under mild conditions. Notably, the directing group can be removed directly in situ along the catalytic process

  据报道，一种新的无痕导向基团2-（羟甲基）吡啶可用于无Cp *的钴催化的CH活化/环化反应，以合成异喹啉酮。该反应表现出良好的官能团耐受性，在温和条件下提供的产物具有良好的分离产率。值得注意的是，可以在催化过程中直接就地除去导向基团。
• Rh( <scp>III</scp> )‐Catalyzed Diverse C—H Functionalization of Iminopyridinium Ylides
  作者：Zhenzhen Dong、Pengfei Li、Xingwei Li、Bingxian Liu

  DOI：10.1002/cjoc.202100203

  日期：2021.9

  Divergent synthesis of useful skeletons has been realized via rhodium(III)-catalyzed C—H activation of iminopyridinium ylides and coupling with various unsaturated coupling reagents. Isocoumarins and isoquinolones were obtained via cleavage of the C—N or N—N bond in the ylidic directing group, while fluorinated alkenes were delivered with the directing group intact. The reactions occurred with wide

  通过铑（III）催化的亚氨基吡啶鎓叶立德的CH活化并与各种不饱和偶联剂偶联，已经实现了有用骨架的发散合成。异香豆素和异喹诺酮获得经由所述C-N或N-N键的ylidic导向基团中的裂解，而氟化烯烃用的导向基团完整递送。该反应在氧化还原中性和耐空气条件下以广泛的底物范围和良好的效率发生。代表性产品表现出固态荧光特性和对人类癌细胞的抑制生物活性。
• Rhodium(<scp>iii</scp>)-catalyzed oxidative annulation of isoquinolones with allyl alcohols: synthesis of isoindolo[2,1-<i>b</i>]isoquinolin-5(7<i>H</i>)-ones
  作者：Jinyuan Jiang、Jidan Liu、Zhenke Yang、Jieying Zheng、Xin Tian、Liyao Zheng、Zhao-Qing Liu

  DOI：10.1039/d1ob02305e

  日期：——

  An efficient rhodium(III)-catalyzed direct C–H oxidative annulation of isoquinolones with allyl alcohols as C1 synthons has been successfully developed. This protocol enables the straightforward synthesis of structurally diverse isoindolo[2,1-b]isoquinolin-5(7H)-ones with high atom economy, tolerates a broad spectrum of functionalities, and is applicable to one-pot operation from readily available

  已经成功开发了一种高效的铑（III）催化的异喹诺酮类与烯丙醇作为 C1 合成子的直接 C-H 氧化环化。该协议能够直接合成结构多样的 isoindolo [2,1- b ]isoquinolin-5(7 H )-ones，具有高原子经济性，耐受广泛的功能，适用于从现成的N的一锅操作-甲氧基苯甲酰胺。
• Rh(III)-Catalyzed Oxidative Annulation of Isoquinolones with Diazoketoesters Featuring an <i>in Situ</i> Deacylation: Synthesis of Isoindoloisoquinolones and Their Transformation to Rosettacin Analogues
  作者：Shenghai Guo、Lincong Sun、Fang Wang、Xinying Zhang、Xuesen Fan

  DOI：10.1021/acs.joc.8b01982

  日期：2018.10.5

  A novel and practical procedure for the preparation of isoindolo[2,1-b]isoquinoline-7-carboxylate derivatives through a Rh(III)-catalyzed oxidative [4 + 1] cycloaddition of isoquinolones with diazoketoesters followed by an in situ deacylation reaction is disclosed. Intriguingly, the title compounds could be easily converted into isoindolo[2,1-b]isoquinolin-5(7H)-ones via de-esterification, which are

  通过Rh（III）催化的异喹诺酮与重氮酮酸酯的氧化[4 +1]环加成，然后进行原位脱酰反应，制备异吲哚并[2,1 - b ]异喹啉-7-羧酸酯衍生物的新颖实用的方法是披露。有趣的是，标题化合物可以很容易地通过去酯化反应转变为异吲哚并[2,1 - b ]异喹啉-5（7 H）-，这是一种罗塞他汀类似物，经常在各种天然生物碱和合成药物分子中发现。