Citation: Yu Jieqiang, Jia Jun, Wang Xingwang. Synthesis of a Type of Linear β, γ-Unsaturated α-Keto Tryptophol Ester Compounds[J]. Chinese Journal of Organic Chemistry, ;2020, 40(9): 2778-2787. doi: 10.6023/cjoc202005051 shu

Synthesis of a Type of Linear β, γ-Unsaturated α-Keto Tryptophol Ester Compounds

  • Corresponding author: Jia Jun, jiajun@suda.edu.cn Wang Xingwang, wangxw@suda.edu.cn
  • Received Date: 19 May 2020
    Revised Date: 22 June 2020
    Available Online: 8 July 2020

    Fund Project: the National Natural Science Foundation of China 21971176Project supported by the National Natural Science Foundation of China (No. 21971176)

Figures(1)

  • Tryptophol derivatives are very important compounds with wide spectrum of pharmaceutical and physiological activity. Herein, the esterification reaction of trypthol and its derivatives with β, γ-unsaturated α-keto acids was reported by the use of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) and 1-hydroxybenzotriazole (HOBt) as conden-sation reagents. A series of β, γ-unsaturated α-keto trypanol ester derivatives were prepared in moderate to high yields. This method has advantages of riched functional group tolerance, readily available starting materials and easy operation.
  • 加载中
    1. [1]

      Emerit, M. B.; Riad, M.; Fattaccini, C. M.; Hamon, M. J. Neurochem. 1993, 60, 2059.  doi: 10.1111/j.1471-4159.1993.tb03490.x

    2. [2]

      (a) López-Noguera, S.; Petri, C.; Alburquerque, N.; Egea, J.; Burgos, L. Plant Sci. 2008, 175, 777.
      (b) Iqbal, N.; Trivellini, A.; Masood, A.; Ferrante, A.; Petri, N. A. Plant Physiol. Biochem. 2013, 73, 128.
      (c) Nongmaithem, S.; Devulapalli, S.; Sreelakshmi, Y.; Sharma, R. Plant Sci. 2020, 291, 110358.
      (d) Zhou, W. G.; Chen, F.; Meng, Y. J.; Chandrasekaran, U.; Luo, X. F. Plant Physiol. Biochem. 2020, 148, 228.

    3. [3]

      (a) Evans, D. A.; Fandrick, K. R.; Song, H.-J. J. Am. Chem. Soc. 2005, 127, 8942.
      (b) Bandini, M.; Melloni, A.; Piccinelli, F.; Sinisi, R.; Tommasi, S.; Umani-Ronchi, A. J. Am. Chem. Soc. 2006, 128, 1424.
      (c) Poulsen, T. B.; Jørgensen, K. A. Chem. Rev. 2008, 108, 2903.
      (d) You, S.-L.; Cai, Q.; Zeng, M. Chem. Soc. Rev. 2009, 38, 2190.
      (e) Trost, B. M.; Osipov, M.; Dong, G. B. J. Am. Chem. Soc. 2010, 132, 15800.
      (f) Cai, Q.; Liang, X.-W.; Wang, S.-G.; Zhang, J.-W.; Zhang, X.; You, S.-L. Org. Lett. 2012, 14, 5022.

    4. [4]

      Palmieri, A.; Petrini, M. Nat. Prod. Rep. 2019, 36, 490.  doi: 10.1039/C8NP00032H

    5. [5]

      (a) Kong, S. J.; Zhang, J. B.; Li, X.; Pan. H.; Guo, D. Y. Biochem. Eng. J. 2020, 154, 107432.
      (b) Comaia, S.; Bertazzo, A.; Brughera, M.; Crotti. S. Adv. Clin. Chem. 2020, 95, 107432.

    6. [6]

      Zheng, C.; You, S.-L. Nat. Prod. Rep. 2019, 36, 1589.  doi: 10.1039/C8NP00098K

    7. [7]

      Wu, Q.-F.; Zheng, C.; You, S.-L. Angew. Chem., Int. Ed. 2012, 124, 1712.  doi: 10.1002/ange.201107677

    8. [8]

      Zhuo, C.-X.; Zheng, C.; You, S.-L. Acc. Chem. Res. 2014, 47, 2558.  doi: 10.1021/ar500167f

    9. [9]

      Wu, Q.-F.; Zheng, C.; Zhuo, C.-X.; You, S.-L. Chem. Sci. 2016, 7, 4453.  doi: 10.1039/C6SC00176A

    10. [10]

      Zhou, Y.; Xia, Z.-L.; Gu, Q.; You, S.-L. Org. Lett. 2017, 19, 762.  doi: 10.1021/acs.orglett.6b03610

    11. [11]

      Li, J.-X.; Chen, G.-H.; Webster, J. M. Bioorg. Med. Chem. Lett. 1997, 7, 1349.  doi: 10.1016/S0960-894X(97)00223-0

    12. [12]

      (a) Yamamoto, Y. J. Org. Chem. 1986, 51, 886.
      (b) Fan, Y.-S.; Jiang, Y.-J.; An, D.; Sha, D.; Antilla, J. C.; Zhang, S. Q. Org. Lett. 2014, 16, 6112.
      (c) Schieferdecker, S.; Shabuer, G.; Letzel, A.-C.; Urbansky, B.; Ishida-Ito, M.; Ishida, K.; Cyrulies, M.; Dahse, H.-M.; Pidot, S.; Hertweck, C. ACS Chem. Biol. 2019, 14, 1490.
      (d) Zhang, Y.-S.; Gui, H.-Z.; Wei, Y.; Shi, M. Eur. J. Org. Chem. 2019, 7179.
      (e) Liu, Z.; Zhang, M.-Y.; Wei, Y.; Shi, M. Eur. J. Org. Chem. 2020, 1093.

    13. [13]

      (a) Boger, D. L.; Borzilleri, R. M.; Nukui, S.; Beresis, R. J. Org. Chem. 1997, 62, 4721.
      (b) Santos, L. S.; Pilli, R. A.; Rawal, V. H. J. Org. Chem. 2004, 69, 1283.
      (c) Cheung, C.-M.; Goldberg, F. W.; Magnus, P.; Russell, C. J. J. Am. Chem. Soc. 2007, 129, 12320.
      (d) Santos, L. S.; Theoduloz, C.; Pilli, R. A.; Rodriguez, J. Eur. J. Med. Chem. 2009, 44, 3810.
      (e) Di Gioia, M. L.; Barattucci, A.; Bonaccorsi, P.; Leggio, A.; Minuti, L.; Romio, E.; Temperini, A.; Siciliano, C. RSC Adv. 2014, 4, 2678.
      (f) Dockendorff, C.; Wiedenhoeft, D.; Benoit, A.; Porter, J.; Wu, Y.; Virdi, R.; Shanaa, A. Synthesis 2016, 48, 2413.
      (g) Shelton, J.; Lu, X.; Hollenbaugh, J. A.; Cho, J. H.; Amblard, F.; Schinazi, R. F. Chem. Rev. 2016, 116, 14379.
      (h) Shugrue, C. R.; Featherston, A. L.; Lackner, R. M.; Lin, A.; Miller, S. J. J. Org. Chem. 2018, 83, 4491.

    14. [14]

      Du, Y.; Huang, H.-Y.; Liu, H.; Ruan, Y.-P.; Huang, P.-Q. Synlett 2011, 565.

    15. [15]

      Wang, H.; Zhu, T.-S.; Xu, M.-H. Org. Biomol. Chem. 2012, 10, 9158.  doi: 10.1039/c2ob26316e

    16. [16]

      Han, L.; Liu, C.; Zhang, W.; Shi, X.-X.; You, S.-L. Chem. Commun. 2014, 50, 1231.  doi: 10.1039/C3CC47921H

    17. [17]

      Zhu, L.-F.; Meng, Q.-H.; Fan, W.-Z.; Xie, X.-M.; Zhang, Z.-G. J. Org. Chem. 2010, 75, 6027.  doi: 10.1021/jo101084t

    18. [18]

      Hua, Y.-Z.; Liu, M.-M.; Huang, P.-J.; Song, X.-X.; Wang, M.-C.; Chang, J.-B. Chem.-Eur. J. 2015, 21, 11994.  doi: 10.1002/chem.201501655

    19. [19]

      Cincinelli, R.; Scaglioni, L.; Arnold, N.-A.; Dallavalle, S. Tetrahedron Lett. 2011, 52, 5972.  doi: 10.1016/j.tetlet.2011.08.143

  • 加载中
    1. [1]

      Yue Zhao Yanfei Li Tao Xiong . Copper Hydride-Catalyzed Nucleophilic Additions of Unsaturated Hydrocarbons to Aldehydes and Ketones. University Chemistry, 2024, 39(4): 280-285. doi: 10.3866/PKU.DXHX202309001

    2. [2]

      Aili Feng Xin Lu Peng Liu Dongju Zhang . Computational Chemistry Study of Acid-Catalyzed Esterification Reactions between Carboxylic Acids and Alcohols. University Chemistry, 2025, 40(3): 92-99. doi: 10.12461/PKU.DXHX202405072

    3. [3]

      Lijuan Liu Xionglei Wang . Preparation of Hydrogels from Waste Thermosetting Unsaturated Polyester Resin by Controllable Catalytic Degradation: A Comprehensive Chemical Experiment. University Chemistry, 2024, 39(11): 313-318. doi: 10.12461/PKU.DXHX202403060

    4. [4]

      Zhuoming Liang Ming Chen Zhiwen Zheng Kai Chen . Multidimensional Studies on Ketone-Enol Tautomerism of 1,3-Diketones By 1H NMR. University Chemistry, 2024, 39(7): 361-367. doi: 10.3866/PKU.DXHX202311029

    5. [5]

      Yukun Chang Haoqin Huang Baolei Wang . Preparation of Trans-Cinnamic Acid via “One-Pot” Protocol of Aldol Condensation-Hydrolysis Reaction: Recommending an Improved Organic Synthesis Experiment. University Chemistry, 2024, 39(4): 322-328. doi: 10.3866/PKU.DXHX202309095

    6. [6]

      Yifeng TANPing CAOKai MAJingtong LIYuheng WANG . Synthesis of pentaerythritol tetra(2-ethylthylhexoate) catalyzed by h-MoO3/SiO2. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2155-2162. doi: 10.11862/CJIC.20240147

    7. [7]

      Liang TANGJingfei NIKang XIAOXiangmei LIU . Synthesis and X-ray imaging application of lanthanide-organic complex-based scintillators. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1892-1902. doi: 10.11862/CJIC.20240139

    8. [8]

      Yiling Wu Peiyao Jin Shenyue Tian Ji Zhang . The Star of Sugar Substitutes: An Interview of Erythritol. University Chemistry, 2024, 39(9): 22-27. doi: 10.12461/PKU.DXHX202404034

    9. [9]

      Mei Yan Rida Feng Yerdos·Tohtarkhan Biao Long Li Zhou Chongshen Guo . Expansion and Extension of Liquid Saturated Vapor Measurement Experiment. University Chemistry, 2024, 39(3): 294-301. doi: 10.3866/PKU.DXHX202308103

    10. [10]

      Ping Song Nan Zhang Jie Wang Rui Yan Zhiqiang Wang Yingxue Jin . Experimental Teaching Design on Synthesis and Antitumor Activity Study of Cu-Pyropheophorbide-a Methyl Ester. University Chemistry, 2024, 39(6): 278-286. doi: 10.3866/PKU.DXHX202310087

    11. [11]

      Zhanggui DUANYi PEIShanshan ZHENGZhaoyang WANGYongguang WANGJunjie WANGYang HUChunxin LÜWei ZHONG . Preparation of UiO-66-NH2 supported copper catalyst and its catalytic activity on alcohol oxidation. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 496-506. doi: 10.11862/CJIC.20230317

    12. [12]

      Xinhao Yan Guoliang Hu Ruixi Chen Hongyu Liu Qizhi Yao Jiao Li Lingling Li . Polyethylene Glycol-Ammonium Sulfate-Nitroso R Salt System for the Separation of Cobalt (II). University Chemistry, 2024, 39(6): 287-294. doi: 10.3866/PKU.DXHX202310073

    13. [13]

      Zhaoxuan ZHULixin WANGXiaoning TANGLong LIYan SHIJiaojing SHAO . Application of poly(vinyl alcohol) conductive hydrogel electrolytes in zinc ion batteries. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 893-902. doi: 10.11862/CJIC.20240368

    14. [14]

      Yuanyuan Ping Wangqing Kong . 光催化碳氢键官能团化合成1-苯基-1,2-乙二醇. University Chemistry, 2025, 40(6): 238-247. doi: 10.12461/PKU.DXHX202408092

    15. [15]

      Lihui Jiang Wanrong Dong Hua Yang Yongqing Xia Hongjian Peng Jun Yuan Xiaoqian Hu Zihan Zeng Yingping Zou Yiming Luo . Study on Extraction of p-Hydroxyacetophenone. University Chemistry, 2024, 39(11): 259-268. doi: 10.12461/PKU.DXHX202402056

    16. [16]

      Lirui Shen Kun Liu Ying Yang Dongwan Li Wengui Chang . Synthesis and Application of Decanedioic Acid-N-Hydroxysuccinimide Ester: Exploration of Teaching Reform in Comprehensive Applied Chemistry Experiment. University Chemistry, 2024, 39(8): 212-220. doi: 10.3866/PKU.DXHX202312035

    17. [17]

      Jinghua Wang Yanxin Yu Yanbiao Ren Yesheng Wang . Integration of Science and Education: Investigation of Tributyl Citrate Synthesis under the Promotion of Hydrate Molten Salts for Research and Innovation Training. University Chemistry, 2024, 39(11): 232-240. doi: 10.3866/PKU.DXHX202402057

    18. [18]

      Yu PengJiawei ChenYue YinYongjie CaoMochou LiaoCongxiao WangXiaoli DongYongyao Xia . Tailored cathode electrolyte interphase via ethylene carbonate-free electrolytes enabling stable and wide-temperature operation of high-voltage LiCoO2. Acta Physico-Chimica Sinica, 2025, 41(8): 100087-0. doi: 10.1016/j.actphy.2025.100087

    19. [19]

      Ronghao Zhao Yifan Liang Mengyao Shi Rongxiu Zhu Dongju Zhang . Investigation into the Mechanism and Migratory Aptitude of Typical Pinacol Rearrangement Reactions: A Research-Oriented Computational Chemistry Experiment. University Chemistry, 2024, 39(4): 305-313. doi: 10.3866/PKU.DXHX202309101

    20. [20]

      Liangzhen Hu Li Ni Ziyi Liu Xiaohui Zhang Bo Qin Yan Xiong . A Green Chemistry Experiment on Electrochemical Synthesis of Benzophenone. University Chemistry, 2024, 39(6): 350-356. doi: 10.3866/PKU.DXHX202312001

Metrics
  • PDF Downloads(3)
  • Abstract views(897)
  • HTML views(88)

通讯作者: 陈斌, bchen63@163.com
  • 1. 

    沈阳化工大学材料科学与工程学院 沈阳 110142

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索
Address:Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888
Powered By info@rhhz.net

/

DownLoad:  Full-Size Img  PowerPoint
Return