Synthesis of 5,7-dichloro-2-adamantanone

封面

如何引用文章

全文:

开放存取 开放存取
受限制的访问 ##reader.subscriptionAccessGranted##
受限制的访问 订阅存取

详细

The reaction of 2-adamantanecarboxylic acid with an excess of chlorine in the presence of AlCl3 under heating gave 5,7-dichloro-2-adamantanecarboxylic acid. This product was sequentially introduced into the Curtius, deamination, and oxidation reactions to form 5,7-dichloro-2-adamantanone. The resulting product is a key substrate for synthesis of new substances and materials with a set of practically important properties, including both the synthesis of biologically active molecules and systems for chemiluminescent diagnostic methods.

作者简介

M. Skomorokhov

Samara State Technical University

Email: ivleva.ea@samgtu.ru

M. Zaborskaya

Samara State Technical University

Email: ivleva.ea@samgtu.ru

E. Ivleva

Samara State Technical University

Email: ivleva.ea@samgtu.ru

A. Shiryaev

Samara State Technical University

Email: ivleva.ea@samgtu.ru

Yu. Klimochkin

Samara State Technical University

Email: ivleva.ea@samgtu.ru

参考

  1. Stockdale T.P., Williams C.M. Chem. Soc. Rev. 2015, 44, 7737-7763. doi: 10.1039/c4cs00477a
  2. Spilovska K., Zemek F., Korabecny J., Nepovimova E., Soukup O., Windisch M., Kuca K. Curr. Med. Chem. 2016, 23, 3245-3266. doi: 10.2174/0929867323666160525114026
  3. Lamoureux G., Artavia G. Curr. Med. Chem. 2010, 17, 2967-2978. doi: 10.2174/092986710792065027
  4. Ширяев В.А., Климочкин Ю.Н. ХГС. 2020, 56, 626-635.
  5. Shiryaev V.A., Klimochkin Y.N. Chem. Heterocycl. Compd. 2020, 56, 626-635. doi: 10.1007/s10593-020-02712-6
  6. Климочкин Ю.Н., Ширяев В.А., Леонова М.В. Изв. АН. Сер. хим. 2015, 64, 1473-1496.
  7. Klimochkin Y.N., Shiryaev V.A., Leonova M.V. Russ. Chem. Bull. 2015, 64, 1473-1496. doi: 10.1007/s11172-015-1035-y
  8. Shiryaev V.A., Skomorohov M.Yu., Leonova M.V., Bormotov N.I., Serova O.A., Shishkina L.N., Agafonov A.P., Maksyutov R.A., Klimochkin Y.N. Eur. J. Med. Chem. 2021, 221, 113485. doi: 10.1016/j.ejmech.2021.113485
  9. Shiryaev V.A., Radchenko E.V., Palyulin V.A., Zefirov N.S., Bormotov N.I., Serova O.A., Shishkina L.N., Baimuratov M.R., Bormasheva K.M., Gruzd Y.A., Ivleva E.A., Leonova M.V., Lukashenko A.V., Osipov D.V., Osyanin V.A., Reznikov A.N., Shadrikova V.A., Sibiryakova A.E., Tkachenko I.M., Klimochkin Y.N. Eur. J. Med. Chem. 2018, 158, 214-235. doi: 10.1016/j.ejmech.2018.08.009
  10. Климочкин Ю.Н., Ткаченко И.М., Резников А.Н., Ширяев В.А., Казачкова М.С., Ковалев Н.С., Бакулин Д.А., Абросимова Е.Е., Куркин Д.В., Тюренков И.Н. Биоорг. хим. 2021, 47, 823-836.
  11. Klimochkin Y.N., Tkachenko I.M., Reznikov A.N., Shiryaev V.A., Kazachkova M.S., Kovalev N.S., Bakulin D.A., Abrosimova E.E., Kurkin D.V., Tyurenkov I.N. Russ. J. Bioorg. Chem. 2021, 47, 1276-1287. doi: 10.1134/S1068162021060108
  12. Liu Z., Qiu X., Mak S., Guo B., Hu S., Wang J., Luo F., Xu D., Sun Y., Zhang G., Cui G., Wang Y., Zhang Z., Han Y. Chem.-Biol. Interact. 2020, 325, 109020. doi: 10.1016/j.cbi.2020.109020
  13. Mak S., Liu Z., Wu L., Guo B., Luo F., Liu Z., Hu S., Wang J., Cui G., Sun Y., Wang Y., Zhang G., Han Y., Zhang Z. ACS Chem. Neurosci. 2020, 11, 314-327. doi: 10.1021/acschemneuro.9b00242
  14. Luo F., Wu L., Zhang Z., Zhu Z., Liu Z., Guo B., Li N., Ju J., Zhou Q., Li S., Yang X., Mak S., Han Y., Sun Y., Wang Y., Zhang G., Zhang Z. Br. J. Pharmacol. 2019, 176, 3318-3335. doi: 10.1111/bph.14763
  15. Ryan L.S., Nakatsuka A., Lippert A.R. Results Chem. 2021, 3, 100106. doi: 10.1016/j.rechem.2021.100106
  16. Kagalwala H.N., Reeves R.T., Lippert A.R. Curr. Opin. Chem. Biol. 2022, 68, 102134. doi: 10.1016/j.cbpa.2022.102134
  17. Hananya N., Shabat D. ACS Cent Sci. 2019, 5, 949-959. doi: 10.1021/acscentsci.9b00372
  18. Gutkin S., Green O., Raviv G., Shabat D., Portnoy O. Bioconjugate Chem. 2020, 31, 2488-2493. doi: 10.1021/acs.bioconjchem.0c00500
  19. Hananya N., Shabat D. Angew. Chem. Int. Ed. 2017, 56, 16454-16463. doi: 10.1002/anie.201706969
  20. Gnaim S., Green O., Shabat D. Chem. Commun. 2018, 54, 2073-2085. doi: 10.1039/C8CC00428E
  21. Ryan L.S., Gerberich J., Haris U., Nguyen D., Mason R.P., Lippert A.R. ACS Sens. 2020, 5, 2925-2932. doi: 10.1021/acssensors.0c01393
  22. Ryan L.S., Gerberich J., Cao J., An W., Jenkins B.A., Mason R.P., Lippert A.R. ACS Sens. 2019, 4, 1391-1398. doi: 10.1021/acssensors.9b00360
  23. Ye S., Hananya N., Green O., Chen H., Zhao A.Q., Shen J., Shabat D., Yang D. Angew. Chem. Int. Ed. 2020, 59, 14326-14330. doi: 10.1002/anie.202005429
  24. Schaap A.P., Handley R.S., Giri B.P. Tetrahedron Lett. 1987, 28, 1155-1158. doi: 10.1016/S0040-4039(00)95313-9
  25. Schaap A.P., Handley R.S., Giri B.P. Tetrahedron Lett. 1987, 28, 935-938. doi: 10.1016/S0040-4039(00)95878-7
  26. Schaap A.P., Sandison M.D., Handley R.S. Tetrahedron Lett. 1987, 28, 1159-1162. doi: 10.1016/S0040-4039(00)95314-0
  27. Tzani M.A., Gioftsidou D.K., Kallitsakis M.G., Pliatsios N.V., Kalogiouri N.P., Angaridis P.A., Lykakis I.N., Terzidis M.A. Molecules. 2021, 26, 7664-7692. doi: 10.3390/molecules26247664
  28. Gong Y., Yang M., Lv J., Li H., Gao J., Yuan Z. ChemPlusChem. 2022, 87, e202200054. doi: 10.1002/cplu.202200054
  29. Wang B., Chen Z., Cen X., Liang Y., Tan L., Liang E., Zheng L., Zheng Y., Zhan Z., Cheng K. Chem. Sci. 2022, 13, 2324-2330. doi: 10.1039/D1SC06528A
  30. Babin B.M., Fernandez-Cuervo G., Sheng J., Green O., Ordonez A.A., Turner M.L., Keller L.J., Jain S.K., Shabat D., Bogyo M. ACS Cent. Sci. 2021, 7, 803-814. doi: 10.1021/acscentsci.0c01345
  31. Yang M., Zhang J., Shabat D., Fan J., Peng X. ACS Sens. 2020, 5, 3158-3164. doi: 10.1021/acssensors.0c01291
  32. Scott J.I., Gutkin S., Green O., Thompson E.J., Kitamura T., Shabat D., Vendrell M. Angew. Chem. Int. Ed. 2021, 60, 5699-5703. doi: 10.1002/anie.202011429
  33. Huang J., Jiang Y., Li J., Huang J., Pu K. Angew. Chem. Int. Ed. 2021, 60, 3999-4003. doi: 10.1002/anie.202013531
  34. Sabelle S., Hydrio J., Leclerc E., Mioskowski C., Renard P.-Y. Tetrahedron Lett. 2002, 43, 3645-3648. doi: 10.1016/S0040-4039(02)00617-2
  35. Roeschlaub C.A., Sammes P.G. J. Chem. Soc. Perkin Trans. 1. 2000, 2243-2248. doi: 10.1039/B002101F
  36. Bruemmer K.J., Green O., Su T.A., Shabat D., Chang C.J. Angew. Chem. Int. Ed. 2018, 57, 7508-7512. doi: 10.1002/anie.201802143
  37. Hananya N., Green O., Blau R., Satchi-Fainaro R., Shabat D. Angew. Chem. Int. Ed. 2017, 56, 11793-11796. doi: 10.1002/anie.201705803
  38. Das S., Ihssen J., Wick L., Spitz U., Shabat D. Chem. Eur. J. 2020, 26, 3647-3652. doi: 10.1002/chem.202000217
  39. Gnaim S., Gholap S.P., Ge L., Das S., Gutkin S., Green O., Shelef O., Hananya N., Baran P.S., Shabat D. Angew. Chem. Int. Ed. 2022, 61, e202202187. doi: 10.1002/anie.202202187
  40. Kamtekar S.D., Pande R., Ayyagari M.S., Marx K.A., Kaplan D.L., Kumar J., Tripathy S. Anal. Chem. 1996, 68, 216-220. doi: 10.1021/ac950681u
  41. Trofimov A.V., Mielke K., Vasil'ev R.F., Adam W. Photochem. Photobiol. 1996, 63, 463-467. doi: 10.1111/j.1751-1097.1996.tb03070.x
  42. https://www.oxfordbiosystems.com/Portals/0/PDF/Research/Neogen-Immunoassay-Reagents.pdf
  43. Ивлева Е.А., Морозова А.И., Сучилин И.Д., Ширяев А.К., Климочкин Ю.Н. ЖОрХ. 2020, 56, 1242-1250.
  44. Ivleva E.A., Morozova A.I., Suchilin I.D., Shiryaev A.K., Klimochkin Y.N. Russ. J. Org. Chem. 2020, 56, 1399-1406. doi: 10.1134/S1070428020080102
  45. Cvitas D.S., Savin B., Mlinaric-Majerski K. Croat. Chem. Acta. 2004, 77, 619-625.
  46. Srivastava S., Cheung C.K., le Noble W.J. Magn. Reson. Chem. 1985, 23, 232-235. doi: 10.1002/mrc.1260230404
  47. Wagner G., Knoll W., Bobek M.M., Brecker L., van Herwijnen H.W.G., Brinker U.H. Org. Lett. 2010, 12, 332-335. doi: 10.1021/ol902667a
  48. Зефирова О.Н., Селюнина Е.В., Аверина Н.В., Зык Н.В., Зефиров Н.С. ЖОрХ. 2002, 38, 1176-1180.
  49. Zefirova O.N., Selyunina E.V., Averina N.V., Zyk N.V., Zefirov N.S. Russ. J. Org. Chem. 2002, 38, 1125-1129. doi: 10.1023/A:1020989123733

补充文件

附件文件
动作
1. JATS XML
下载

版权所有 © Russian Academy of Sciences, 2023