2,4-dimethyl-3-phenyl-1,2-dihydro-isoquinolin-1(2H)-one | 51089-64-6

• 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: 2,4-dimethyl-3-phenyl-1,2-dihydro-isoquinolin-1(2H)-one
• 英文别名: 1,2-Dihydro-2,4-dimethyl-3-phenylisoquinolin-1-one；2,4-Dimethyl-3-phenyl-1(2H)-isoquinolinone；2,4-dimethyl-3-phenylisoquinolin-1(2H)-one；2,4-dimethyl-3-phenyl-1-isoquinolone；2,4-dimethyl-3-phenyl-2H-isoquinolin-1-one；2,4-Dimethyl-3-phenylisochinolin-1(2H)-on；1(2H)-Isoquinolinone, 2,4-dimethyl-3-phenyl-；2,4-dimethyl-3-phenylisoquinolin-1-one
• CAS: 51089-64-6
• 化学式: C₁₇H₁₅NO
• 分子量: 249.312
• InChiKey: ZZQPZPATVZEOGK-UHFFFAOYSA-N

物化性质

• 熔点：
  95-96 °C
• 沸点：
  423.9±45.0 °C(Predicted)
• 密度：
  1.147±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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-(α-ethylbenzylidene)methylamine 在 吡啶 、 三氯化铝 、 亚硝酸异戊酯 、 三氯乙酸 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 反应 8.17h， 生成 2,4-dimethyl-3-phenyl-1,2-dihydro-isoquinolin-1(2H)-one
  参考文献：
  名称：

  Synthesis of 3-phenylisoquinolones by reaction of simple pyrroline-2,3-diones with benzyne. New mechanistic considerations

  摘要：

  3-Phenylisoquinolones were obtained by cycloaddition of benzyne to 5-phenylpyrroline-2,3-diones. New mechanistic hypotheses for these transformations are discussed.

  DOI：

  10.1021/jo00063a034

文献信息

• Electrooxidative Ruthenium-Catalyzed C−H/O−H Annulation by Weak <i>O</i> -Coordination
  作者：Youai Qiu、Cong Tian、Leonardo Massignan、Torben Rogge、Lutz Ackermann

  DOI：10.1002/anie.201802748

  日期：2018.5.14

  as a powerful strategy for organometallic catalysis, and yet electrocatalytic C−H activation is restricted to strongly N‐coordinating directing groups. The first example of electrocatalytic C−H activation by weak O‐coordination is presented, in which a versatile ruthenium(II) carboxylate catalyst enables electrooxidative C−H/O−H functionalization for alkyne annulations in the absence of metal oxidants;

  电催化已被认为是有机金属催化的有力策略，但是电催化CH活化仅限于强N配位的导向基团。给出了通过弱O配位进行电催化C-H活化的第一个例子，其中通用的羧酸钌（II）催化剂可在没有金属氧化剂的情况下实现炔烃环化的电氧化C / H / OH功能化。从而利用可持续的电力作为唯一的氧化剂。机械学的见解为简便的有机金属CH钌钌化和关键钌（0）中间体的有效电化学再氧化提供了有力的支持。
• Ruthenium-Catalyzed Oxidative Annulation by Cleavage of CH/NH Bonds
  作者：Lutz Ackermann、Alexander V. Lygin、Nora Hofmann

  DOI：10.1002/anie.201101943

  日期：2011.7.4

  Bond activation in action: Unprecedented ruthenium‐catalyzed oxidative annulations of alkynes through cleavage of CH bonds set the stage for an efficient 1(2H)‐isoquinolone synthesis with ample scope (see scheme; tAm=tert‐amyl). Mechanistic studies provided strong evidence for a rate‐limiting CH bond metalation through carboxylate assistance.

  键活化在动作：以C裂解炔烃的前所未有的钌催化氧化annulations  H键设置阶段为一个有效的1（2 ħ）-isoquinolone合成了充足的范围（参见方案;吨AM =叔戊基）。机理研究为通过羧酸盐协助限速CH键金属化提供了有力证据。
• Additive Effects in the Palladium-Catalyzed Carboiodination of Chiral<i>N</i>-Allyl Carboxamides
  作者：David A. Petrone、Hyung Yoon、Harald Weinstabl、Mark Lautens

  DOI：10.1002/anie.201404007

  日期：2014.7.21

  reductive elimination. Herein, we present our finding that tertiary amines act as weakly coordinating ligands which significantly enhance diastereoselectivity in the Pd/QPhos‐catalyzed carboiodination of chiral N‐allyl carboxamides. This methodology allows efficient access to enantioenriched and densely functionalized dihydroisoquinolinones, and has been applied toward the asymmetric formal synthesis of (+)‐corynoline

  最近，使用钯催化作为合成有机卤化物的手段受到了越来越多的关注。在已报道的方法中，有Pd催化的碳碘化反应，它使用非常庞大的配体来促进Pd II的碳-卤素还原消除。作为关键的催化步骤。当接近表现出低立体选择性的底物时，催化剂的疑难解答变得困难，因为已知很少有能促进关键还原消除的配体。在这里，我们提出我们的发现，叔胺充当弱配位配体，可显着增强Pd / QPhos催化的手性N-烯丙基羧酰胺的碳碘化中的非对映选择性。这种方法学可以有效地获得对映体富集和功能密集的二氢异喹啉酮，并已被用于（+）-炔诺琳的不对称形式合成。
• Remote C(sp ³ )−H Acylation of Amides and Cascade Cyclization via N‐Heterocyclic Carbene Organocatalysis
  作者：Qing‐Zhu Li、Rong Zeng、Yang Fan、Yan‐Qing Liu、Ting Qi、Xiang Zhang、Jun‐Long Li

  DOI：10.1002/anie.202116629

  日期：2022.4.4

  An N-heterocyclic carbene catalyzed remote C(sp3)−H acylation of amides was developed, and also combined with a cascade cyclization. Over 120 functionalized δ-amino ketones and isoquinolinones with diverse substituents were synthesized in up to 99 % yield under mild conditions. Preliminary mechanistic investigations shed light on the organocatalytic radical reaction mechanism.

  开发了一种 N-杂环卡宾催化的酰胺的远程 C(sp 3 )-H 酰化，并结合了级联环化。在温和条件下以高达 99% 的产率合成了 120 多种具有不同取代基的功能化 δ-氨基酮和异喹啉酮。初步的机理研究揭示了有机催化自由基反应的机理。
• 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。