9-methyl-3,4-diphenyl-2H-pyrido[3,4-b]indol-1(9H)-one | 1232594-37-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 9-methyl-3,4-diphenyl-2H-pyrido[3,4-b]indol-1(9H)-one
• 英文别名: 9-methyl-3,4-diphenyl-2,9-dihydro-1H-pyrido[3,4-b]indol-1-one；9-methyl-3,4-diphenyl-2H-pyrido[3,4-b]indol-1-one
• CAS: 1232594-37-4
• 化学式: C₂₄H₁₈N₂O
• 分子量: 350.42
• InChiKey: GIRKQJVSEPRWCT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  34
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  9-methyl-3,4-diphenyl-2H-pyrido[3,4-b]indol-1(9H)-one 、 对苯醌 在 bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] 、 sodium acetate 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以99%的产率得到
  参考文献：
  名称：

  Ir(III)-Catalyzed Oxidative Coupling of NH Isoquinolones with Benzoquinone

  摘要：

  The oxidative coupling reactions of NH isoquinolones with 1,4-benzoquinone proceeded efficiently to form spiro compounds in the presence of an Ir(III) catalyst through C-H activation. The reactions have a broad range of substrates, with nearly quantitative yields, without the use of external oxidants. For 1,4-naphthoquinone and other substituted 1,4-benzoquinone the reactions also gave high yields with Cu(OAc)(2)center dot H2O as an external oxidant. A catalytically competent five-membered iridacycle has been isolated and structurally characterized, thus revealing a key intermediate in the catalytic cycle.

  DOI：

  10.1021/acs.orglett.5b01974
• 作为产物：
  描述：

  1-甲基吲哚-2-甲酸 在 草酰氯 、 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 sodium acetate 、 potassium carbonate 、 N,N-二甲基甲酰胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 64.0h， 生成 9-methyl-3,4-diphenyl-2H-pyrido[3,4-b]indol-1(9H)-one
  参考文献：
  名称：

  钌催化异喹啉酮合成到C ？使用氧化指导基团进行H活化

  摘要：

  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。

  DOI：

  10.1002/chem.201102445

文献信息

• Ruthenium-Catalyzed Oxidative Coupling/Cyclization of Isoquinolones with Alkynes through CH/NH Activation: Mechanism Study and Synthesis of Dibenzo[<i>a</i>,<i>g</i>]quinolizin-8-one Derivatives
  作者：Bin Li、Huiliang Feng、Nuancheng Wang、Jianfeng Ma、Haibin Song、Shansheng Xu、Baiquan Wang

  DOI：10.1002/chem.201201862

  日期：2012.10.1

  mechanism of [RuCl2(p‐cymene)}2]‐catalyzed oxidative annulations of isoquinolones with alkynes was investigated in detail. The first step is an acetate‐assisted CH bond activation process to form cyclometalated compounds. Subsequent mono‐alkyne insertion of the RuC bonds of the cyclometalated compounds then takes place. Finally, oxidative coupling of the CN bond of the insertion compounds occurs to

  详细研究了[RuCl 2（p- cymene）} 2 ]催化的异喹诺酮与炔烃氧化环化反应的机理。第一步是乙酸盐辅助的CH键活化过程，以形成环金属化的化合物。随后发生环金属化化合物的RuC键的单炔插入。最后，插入化合物的CN键发生氧化偶联，得到Ru 0夹心复合物，该复合物经过氧化反应以与铜氧化剂再生具有催化活性的Ru II络合物，并释放出所需的二苯并[ a，g]。] quinolizin-8-one衍生物。所有相关中间体均已通过单晶X射线衍射分析进行了充分表征和测定。的[的RuCl 2（p -cymene）} 2 ]催化的ç 与炔异喹诺酮的H键官能合成二苯并[一，克〕喹嗪-8-酮通过C衍生物 H /Ñ  ħ活化还证实。
• Synthesis of β- and γ-Carbolinones via Pd-Catalyzed Direct Dehydrogenative Annulation (DDA) of Indole-carboxamides with Alkynes Using Air as the Oxidant
  作者：Zhuangzhi Shi、Yuxin Cui、Ning Jiao

  DOI：10.1021/ol1007839

  日期：2010.7.2

  A palladium-catalyzed direct dehydrogenative annulation (DDA) of indolecarboxamides with internal alkynes via C−H and N−H bond cleavage using air as the oxidant was developed. With this method, both β- and γ-carbolinones can be easily prepared under the mild conditions.

  有人开发了使用空气作为氧化剂，通过CH和N-H键裂解的钯催化的吲哚羧酰胺与内部炔烃的直接脱氢环化反应（DDA）。用这种方法，可以在温和的条件下容易地制备β-和γ-咔啉酮。
• Ru(II) Catalyzed Oxidative Dehydrogenative Annulation and Spirocyclization of Isoquinolones with N‐Substituted Maleimides
  作者：Kaushik Seal、Biswadip Banerji

  DOI：10.1002/adsc.202300963

  日期：2024.4.23

  Mechanistically dehydrogenative, oxidative C-C followed by C-N cross-coupling and aza-michael reaction pathway led to the corresponding fused and spiro-products respectively. A diversified library of eighty-one (81) such two products were synthesized by employing this methodology. The fused and the spirocyclized polyheterocyclic compounds absorbed at λmax 240-270 nm range, however only spiro-compounds produced

  本文报道了钌(II)催化的无添加剂的不同马来酰亚胺在3,4-二取代异喹诺酮上的氧化、脱氢成环反应，得到稠合和螺环化的异喹啉-异喹诺酮和异吲哚并-异喹诺酮衍生物。通过简单地改变溶剂和氧化剂，在两种不同的条件下，该方法产生了两种不同的多-N-杂环化产物。在使用 Ru(II) 催化剂的邻位 C-H 活化中，策略性地使用异喹诺酮-NH 作为内部导向基团。机械脱氢、氧化C-C，随后是C-N交叉偶联和氮杂迈克尔反应途径，分别产生相应的稠合和螺环产物。采用这种方法合成了包含八十一 (81) 种这样两种产品的多样化库。稠合和螺环化多杂环化合物在 λmax 240-270 nm 范围内吸收，但只有螺环化合物在 λem 391-450 nm 范围内产生蓝色荧光。
• 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。
• Ir(III)-Catalyzed Oxidative Coupling of NH Isoquinolones with Benzoquinone
  作者：Tao Zhou、Liubo Li、Bin Li、Haibin Song、Baiquan Wang

  DOI：10.1021/acs.orglett.5b01974

  日期：2015.9.4

  The oxidative coupling reactions of NH isoquinolones with 1,4-benzoquinone proceeded efficiently to form spiro compounds in the presence of an Ir(III) catalyst through C-H activation. The reactions have a broad range of substrates, with nearly quantitative yields, without the use of external oxidants. For 1,4-naphthoquinone and other substituted 1,4-benzoquinone the reactions also gave high yields with Cu(OAc)(2)center dot H2O as an external oxidant. A catalytically competent five-membered iridacycle has been isolated and structurally characterized, thus revealing a key intermediate in the catalytic cycle.