phenyl(9H-pyrido[3,4-b]indol-1-yl)methanone | 906067-36-5

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: phenyl(9H-pyrido[3,4-b]indol-1-yl)methanone
• 英文别名: 9H-hydro-β-carboline-1-yl(phenyl)methanone；Methanone, phenyl-9H-pyrido[3,4-b]indol-1-yl-
• CAS: 906067-36-5
• 化学式: C₁₈H₁₂N₂O
• 分子量: 272.306
• InChiKey: ZVQHFEFCMIBJJF-UHFFFAOYSA-N

物化性质

• 熔点：
  135-138 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  525.7±30.0 °C(Predicted)
• 密度：
  1.313±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  phenyl(9H-pyrido[3,4-b]indol-1-yl)methanone 在 dipotassium peroxodisulfate 、 palladium diacetate 、 三氟乙酸 作用下， 反应 48.0h， 生成 (2,6-dimethoxyphenyl)(9H-pyrido[3,4-b]indol-1-yl)methanone
  参考文献：
  名称：

  Pd(OAc)₂-catalysed regioselective alkoxylation of aryl (β-carbolin-1-yl)methanones via β-carboline directed ortho-C(sp²)–H activation of an aryl ring

  摘要：

  通过Pd(OAc)2催化的芳基(β-咔啉-1-基)甲酮的定向烷氧基化合成(2-烷氧基苯基)(9H-吡啶并[3,4-b]吲哚-1-基)甲酮，利用β-咔啉引导的芳基骨架在氧化条件下进行ortho-C(sp2)-H活化。

  DOI：

  10.1039/c5ob01500f
• 作为产物：
  描述：

  1-benzoyl-3,4-dihydro-β-carboline 在 氧气 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以99%的产率得到phenyl(9H-pyrido[3,4-b]indol-1-yl)methanone
  参考文献：
  名称：

  Regioselective photo-oxidation of 1-benzyl-4,9-dihydro-3H-β-carbolines

  摘要：

  本文展示了一系列基于β-卡波啉的天然产物fascaplysin的类似物的合成；这些化合物是通过1-苄基-4,9-二氢-3H-β-卡波啉的创新光氧化反应作为关键步骤生产的。

  DOI：

  10.1039/b604922b

文献信息

• β-Carboline-directed decarboxylative acylation of ortho-C(sp²)–H of the aryl ring of aryl(β-carbolin-1-yl)methanones with α-ketoacids under palladium catalysis
  作者：Shivalinga Kolle、Sanjay Batra

  DOI：10.1039/c6ra11811a

  日期：——

  A palladium-catalysed β-carboline directed decarboxylative acylation of ortho-C(sp2)–H of the aryl ring of aryl(β-carbolin-1-yl)methanones using α-oxocarboxylic acid as the acyl ion equivalent to form (2-aroylaryl)(β-carbolin-2-yl)methanones is described. The utility of these products for preparing β-carboline-tethered phthalazine systems is also demonstrated.

  以α-氧代羧酸为等效形式的钯催化的β-咔啉对芳基（β-carbolin-1-yl）甲酮的芳基环的邻-C（sp 2）-H进行直接脱羧酰化（2描述了-（芳酰基芳基）（β-咔啉-2-基）甲酮。还证明了这些产品在制备β-咔啉系酞菁体系中的实用性。
• Photoredox Generated Vinyl Radicals: Synthesis of Bisindoles and β-Carbolines
  作者：Neha Chalotra、Ajaz Ahmed、Masood Ahmad Rizvi、Zakir Hussain、Qazi Naveed Ahmed、Bhahwal Ali Shah

  DOI：10.1021/acs.joc.8b02193

  日期：2018.12.7

  A photoredox catalyzed approach enabling use of alkynes as surrogate of 2-oxoaldehydes/1,2-diones is reported. The method overcomes the difficulty associated with application of unsubstituted aliphatic α-oxoaldehydes, which has hitherto limited their general use. Indoles, tryptamine, and tryptophan methyl ester participated in the reaction to give a variety of α-oxo based analogues. Quantum yield investigations

  据报道，光氧化还原催化的方法能够使用炔烃作为2-氧醛/ 1,2-二酮的替代物。该方法克服了与未取代的脂族α-氧醛的施用相关的困难，该困难迄今限制了它们的一般用途。吲哚，色胺和色氨酸甲酯参与了反应，得到了多种基于α-氧代的类似物。量子产率研究支持自由基链机制。
• A Cascade Coupling Strategy for One-Pot Total Synthesis of β-Carboline and Isoquinoline-Containing Natural Products and Derivatives
  作者：Yan-Ping Zhu、Mei-Cai Liu、Qun Cai、Feng-Cheng Jia、An-Xin Wu

  DOI：10.1002/chem.201301734

  日期：2013.7.29

  Multi‐birds with one stone: A cascade coupling strategy was developed for the synthesis of β‐carbolines. The method can direct the synthesis of β‐carboline and isoquinoline‐containing natural products with high yields. Moreover, this protocol can also be further applied towards the total synthesis of natural products fascaplysin and papaverin (see scheme).

  一块石头的多鸟：开发了一种级联偶联策略来合成β-咔啉。该方法可以指导高产率合成含β-咔啉和异喹啉的天然产物。此外，该方案还可以进一步应用于天然产物fascaplysin和papaverin的全合成（参见方案）。
• Synthesis, crystal structure and biological activity of β-carboline based selective CDK4-cyclin D1 inhibitors
  作者：Marcos D. García、A. James Wilson、Daniel P. G. Emmerson、Paul R. Jenkins、Sachin Mahale、Bhabatosh Chaudhuri

  DOI：10.1039/b613861f

  日期：——

  The design, synthesis and biological activity of a series of non-planar dihydro-β-carboline and β-carboline-based derivatives of the toxic anticancer agent fascaplysin is presented. We show these compounds to be selective inhibitors of CDK4 over CDK2 with an IC50 (CDK4-cyclin D1) = 11 µmol for the best compound in the series 4d. The crystallographic analysis of some of the compounds synthesised (3b/d and 4a–d) was carried out, in an effort to estimate the structural similarities between the designed inhibitors and the model compound fascaplysin.

  本文展示了一系列非平面二氢-β-卡巴啉和基于β-卡巴啉的衍生物的设计、合成和生物活性，这些衍生物源自毒性抗癌剂法斯卡普利辛。我们证明这些化合物是CDK4的选择性抑制剂，相较于CDK2，系列中最佳化合物4d的IC50（CDK4-细胞周期蛋白D1）为11 µmol。对部分合成化合物（3b/d和4a–d）进行了晶体学分析，以估计设计抑制剂与模型化合物法斯卡普利辛之间的结构相似性。
• Total Syntheses of Eudistomins Y₁-Y₇by an Efficient One-Pot Process of Tandem Benzylic Oxidation and Aromatization of 1-Benzyl-3,4-dihydro-β-Carbolines
  作者：Tien Ha Trieu、Jing Dong、Qiang Zhang、Bo Zheng、Tian-Zhuo Meng、Xia Lu、Xiao-Xin Shi

  DOI：10.1002/ejoc.201300080

  日期：2013.6

  The first total synthesis of eudistomin Y7 (7) and total syntheses of eudistomins Y1–Y6 (1–6) are described. An efficient room-temperature conversion of 1-benzyl-3,4-dihydro-β-carbolines (11) into 1-benzoyl-β-carbolines (14) by a one-pot process of tandem benzylic oxidation and aromatization as the key step of these total syntheses was also studied in detail.

  描述了eudistomin Y7 (7) 的首次全合成和eudistomin Y1–Y6 (1–6) 的全合成。1-苄基-3,4-二氢-β-咔啉（11）在室温下通过串联苄基氧化和芳构化的一锅法高效转化为1-苯甲酰基-β-咔啉（14）作为关键步骤还详细研究了这些全合成。