2-benzylidene-1-oxo-1,2,3,4-tetrahydrocarbazole

• 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: 2-benzylidene-1-oxo-1,2,3,4-tetrahydrocarbazole
• 英文别名: 2-benzylidene-1,2,3,4-tetrahydrocarbazol-1-one；(2E)-2-benzylidene-4,9-dihydro-3H-carbazol-1-one
• 化学式: C₁₉H₁₅NO
• 分子量: 273.334
• InChiKey: JCUHEMJWSFFFOR-WYMLVPIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  32.9
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-benzylidene-1-oxo-1,2,3,4-tetrahydrocarbazole 以80%的产率得到
  参考文献：
  名称：

  GRINEV A. N.; NIKOLAEVA I. N.; ALTUXOVA L. B., XIMIYA GETEROTSIKL. SOEDIN. , 1976, HO 6, 794-796

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3,4,9-四氢-1H-咔唑-1-酮 、 苯甲醛 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 生成 2-benzylidene-1-oxo-1,2,3,4-tetrahydrocarbazole
  参考文献：
  名称：

  Synthesis of novel spiropyrrolizidines as potent antimicrobial agents for human and plant pathogens

  摘要：

  A series of novel dispirooxindolopyrrolizidine derivatives have been synthesized through 1,3-dipolar cycloaddition reaction of azomethine ylide generated from proline and isatin with the dipolarophile (E)-2-arylidine-1-keto carbazoles. The synthesized cycloadducts were evaluated for antimicrobial activities. Compounds 7d and 7e showed relatively good antibacterial and antifungal activities. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.02.065

文献信息

• Synthetic Utility of 2-Benzylidene-1,2,3,4-tetrahydrocarbazol-1-ones. A Facile Syntheses of Pyrano[2,3-a]carbazoles, Pyrido[2,3-a]carbazoles and Pyridazino[3,4-a]carbazoles
  作者：Isravel Antony Danish、Karnam Jayarampillai Rajendra Prasad

  DOI：10.1135/cccc20050223

  日期：——

  2-Benzylidene-1,2,3,4-tetrahydrocarbazol-1-ones 1, synthons easily accessible from the corresponding 1,2,3,4-tetrahydrocarbazol-1-ones, were utilized in the synthesis of fused carbazoles. In accordance, the reaction of 1 with malononitrile yielded pyrano[2,3-a]carbazoles 2a and 2d or pyrido[2,3-a]carbazoles 2b, 2c and 2e. The reaction of 1 with thiocarbohydrazide or thiosemicarbazide under basic conditions afforded pyridazino[3,4-a]carbazoles 3 or thiol substituted pyridazino[3,4-a]carbazoles 4, respectively, in good yields. The formation of the hitherto unknown compounds was well supported by plausible mechanisms. The products formed were characterized by IR, ¹H NMR, ¹³C NMR, mass spectral methods and by elemental analysis.

  2-苄基亚甲基-1,2,3,4-四氢咔唑-1-酮1，易于从相应的1,2,3,4-四氢咔唑-1-酮合成物中获得的合成子，在合成融合咔唑化合物中得到应用。相应地，1与马来酸二腈反应生成吡喃并[2,3-a]咔唑2a和2d，或吡啶并[2,3-a]咔唑2b、2c和2e。1与硫代甲酰肼或硫代脲在碱性条件下反应生成吡啶并[3,4-a]咔唑3或硫代取代的吡啶并[3,4-a]咔唑4，收率较高。对迄今为止未知的化合物的形成得到了合理的机制支持。产物通过红外光谱、1H核磁共振、13C核磁共振、质谱方法和元素分析进行了表征。
• An Elegant Synthetic Route to 3-Cyano-5,6-dihydro-2-ethoxy-4-phenyl-pyrido[2,3-a]carbazoles
  作者：Isravel A. Danish、Karnam J. R. Prasad

  DOI：10.1515/znb-2004-0115

  日期：2004.1.1

  2-Benzylidene-1-oxo-1,2,3,4-tetrahydrocarbazoles (1a - e) obtained from the corresponding 1- oxo-1,2,3,4-tetrahydrocarbazoles on reaction with malononitrile in dry benzene with sodium hydride afforded 3-cyano-5,6-dihydro-2-ethoxy-4-phenyl-pyrido[2,3-a]carbazoles (2a - e) in good yields. A plausible mechanism for the formation of the title compound has been proposed and all the compounds were characterised by IR, NMR, mass spectral methods and elemental analysis.

  通过将相应的1-氧代-1,2,3,4-四氢咔唑与丙二腈在干苯中与氢化钠反应，得到2-苯甲基亚甲基-1-氧代-1,2,3,4-四氢咔唑（1a-e），并以良好的产率得到3-氰基-5,6-二氢-2-乙氧基-4-苯基吡啶[2,3-a]咔唑（2a-e）。提出了形成标题化合物的可能机理，并通过红外、核磁共振、质谱方法和元素分析对所有化合物进行了表征。

• Synthesis of novel spiropyrrolizidines as potent antimicrobial agents for human and plant pathogens
  作者：Govindasami Periyasami、Raghavachary Raghunathan、Gangadharan Surendiran、Narayanasamy Mathivanan

  DOI：10.1016/j.bmcl.2008.02.065

  日期：2008.4

  A series of novel dispirooxindolopyrrolizidine derivatives have been synthesized through 1,3-dipolar cycloaddition reaction of azomethine ylide generated from proline and isatin with the dipolarophile (E)-2-arylidine-1-keto carbazoles. The synthesized cycloadducts were evaluated for antimicrobial activities. Compounds 7d and 7e showed relatively good antibacterial and antifungal activities. (C) 2008 Elsevier Ltd. All rights reserved.
• Regioselective synthesis and antimicrobial screening of novel ketocarbazolodispiropyrrolidine derivatives
  作者：Govindasami Periyasami、Raghavachary Raghunathan、Gangadharan Surendiran、Narayanasamy Mathivanan

  DOI：10.1016/j.ejmech.2008.07.009

  日期：2009.3

  A series of novel dispiropyrrolidine derivatives have been synthesized through 1,3-dipolar cycloaddition reaction of azomethine ylide generated from sarrosin and di/tri ketone with the dipolarophile (E)-2-arylidine-1-keto-carbazoles.The cycloadducts ketocarbazalo spiro N-methyl pyrrolidines showed the most interesting antimicrobial activity at lower concentration. (C) 2008 Elsevier Masson SAS. All rights reserved.
• GRINEV A. N.; NIKOLAEVA I. N.; ALTUXOVA L. B., XIMIYA GETEROTSIKL. SOEDIN. <KGSS-AQ>, 1976, HO 6, 794-796
  作者：GRINEV A. N.、 NIKOLAEVA I. N.、 ALTUXOVA L. B.

  DOI：——

  日期：——