5-methyldibenzo[cd,f]indol-4(5H)-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 5-methyldibenzo[cd,f]indol-4(5H)-one
• 英文别名: 10-Methyl-10-azatetracyclo[7.6.1.02,7.012,16]hexadeca-1(16),2,4,6,8,12,14-heptaen-11-one
• 化学式: C₁₆H₁₁NO
• 分子量: 233.269
• InChiKey: ZBVOJPXNSAEYBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  methyl 3-(2-bromophenyl)-3-(2-methyl-3-oxoisoindolin-1-yl)propanoate 在 palladium diacetate 、 potassium carbonate 、 tricyclohexylphosphine tetrafluoroborate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 0.5h， 以51%的产率得到5-methyldibenzo[cd,f]indol-4(5H)-one
  参考文献：
  名称：

  Electrochemical C(sp³)–H Functionalization of γ-Lactams Based on Hydrogen Atom Transfer

  摘要：

  DOI：

  10.1021/acs.orglett.2c01528

文献信息

• Total Synthesis of Aristolactams via a One-Pot Suzuki−Miyaura Coupling/Aldol Condensation Cascade Reaction
  作者：Joa Kyum Kim、Young Ha Kim、Ho Tae Nam、Bum Tae Kim、Jung-Nyoung Heo

  DOI：10.1021/ol801291k

  日期：2008.8.21

  A direct one-pot synthesis of phenanthrene lactams, which employs a Suzuki-Miyaura coupling/aldol condensation cascade reaction of isoindolin-1-one with 2-formylphenylboronic acid, has been developed. The approach is used to efficiently produce a number of natural aristolactams, such as aristolactam BII (cepharanone B), aristolactam BIII, aristolactam FI (piperolactam A), N-methyl piperolactam A, and

  已经开发了一种直接一锅合成菲内酰胺的方法，该方法利用了异吲哚啉-1-酮与2-甲酰基苯基硼酸的Suzuki-Miyaura偶联/醛醇缩合级联反应。该方法用于有效地生产许多天然的马兜铃内酰胺，例如马兜铃内酰胺BII（头孢兰酮B），马兜铃内酰胺BIII，马兜铃内酰胺FI（哌内酰胺A），N-甲基哌内酰胺A和sauristolactam。
• Total synthesis of aristolactam alkaloids via synergistic C–H bond activation and dehydro-Diels–Alder reactions
  作者：Mallu Chenna Reddy、Masilamani Jeganmohan

  DOI：10.1039/c7sc00161d

  日期：——

  concise total synthesis of aristolactam alkaloids by a synergistic combination of C–H bond activation and dehydro-Diels–Alder reactions is described. To achieve the synthesis two new synthetic methodologies, namely the oxidative cyclization of benzamides with vinyl sulfone leading to 3-methyleneisoindolin-1-ones via a ruthenium-catalyzed C–H bond activation, and a dehydro-Diels–Alder reaction followed by

  描述了通过 C-H 键活化和脱氢-Diels-Alder 反应的协同组合来简明地全合成马兜铃内酰胺生物碱。为了实现合成，采用了两种新的合成方法，即苯甲酰胺与乙烯基砜的氧化环化，通过钌催化的 C-H 键活化生成 3-亚甲基异吲哚啉-1-酮，以及脱氢-狄尔斯-阿尔德反应，然后生成氟化物开发了 3-亚甲基异吲哚啉-1-酮与苯炔的离子介导脱磺酰化。所提出的方法允许从容易获得的起始材料构建所有马兜铃内酰胺环。
• A New Approach to the Synthesis of Aristolactams. Total Synthesis of Cepharanone A and B
  作者：Axel Couture、Eric Deniau、Pierre Grandclaudon、Stéphane Lebrun

  DOI：10.1055/s-1997-1046

  日期：——

  An efficient, concise and tactically new synthesis of aristolactams is described. The key step is the aryne-mediated cyclization of an amino carbanion derived from a phosphorylated halobenzamide derivative. Horner reaction, radical cyclization and ultimate deprotection complete the synthesis of the phenanthrene lactam alkaloids. The viability of the strategy is further illustrated by the synthesis of cepharanone A and B.

  描述了一种高效、简洁且战术新颖的阿里斯托拉克塔姆合成方法。关键步骤是利用芳烯介导的环化反应，将来自磷酸化卤代苯酰胺衍生物的氨基羰基阴离子进行环化。霍纳反应、自由基环化和最终去保护完成了苯并蒽内酯生物碱的合成。该策略的可行性通过合成头孢霉素A和B进一步得到了验证。
• [EN] PHENANTHRENE LACTAM DERIVATIVES HAVING ANTICANCER ACTIVITY AND METHOD FOR THE PREPARATION THEREOF<br/>[FR] DÉRIVÉS DE LACTAME PHÉNANTHRÈNE PRÉSENTANT UNE ACTIVITÉ ANTICANCÉREUSE ET PROCÉDÉ DE PRÉPARATION DE CEUX-CI
  申请人：KOREA RES INST CHEM TECH

  公开号：WO2009051417A3

  公开（公告）日：2009-06-04
• Synthesis of aristolactam analogues and evaluation of their antitumor activity
  作者：Young Lok Choi、Joa Kyum Kim、Sang-Un Choi、Yong-Ki Min、Myung-Ae Bae、Bum Tae Kim、Jung-Nyoung Heo

  DOI：10.1016/j.bmcl.2009.04.020

  日期：2009.6

  A series of natural aristolactams and their analogues have been prepared and evaluated for antitumor activity against human cancer cells, including multi-drug resistant cell lines. Naturally occurring aristolactams, such as aristolactam BII (cepharanone B), aristolactam BIII, aristolactam FI (piperolactam A), N-methyl piperolactam A, and sauristolactam showed moderate antitumor activities in selected cell lines. However, several synthetic aristolactam derivatives exhibited potent antitumor activities against a broad array of cancer cell lines with GI(50) values in the submicromolar range. (C) 2009 Elsevier Ltd. All rights reserved.