WO2013006098A2 - Dérivés de 2,6-diisobornyl phénol - Google Patents

Dérivés de 2,6-diisobornyl phénol Download PDF

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Publication number
WO2013006098A2
WO2013006098A2 PCT/RU2012/000533 RU2012000533W WO2013006098A2 WO 2013006098 A2 WO2013006098 A2 WO 2013006098A2 RU 2012000533 W RU2012000533 W RU 2012000533W WO 2013006098 A2 WO2013006098 A2 WO 2013006098A2
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WO
WIPO (PCT)
Prior art keywords
group
isobornyl
configuration
fragments
formula
Prior art date
Application number
PCT/RU2012/000533
Other languages
English (en)
Russian (ru)
Other versions
WO2013006098A3 (fr
Inventor
Александр Васильевич КУЧИН
Ирина Юрьевна ЧУКИЧЕВА
Ирина Витальевна ФЕДОРОВА
Евгений Владимирович БУРАВЛЕВ
Original Assignee
Федеральное Государственное Бюджетное Учреждение Науки Институт Химии Коми Научного Центра Уральского Отделения Российской Академии Наук
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from RU2011127776/04A external-priority patent/RU2575294C2/ru
Application filed by Федеральное Государственное Бюджетное Учреждение Науки Институт Химии Коми Научного Центра Уральского Отделения Российской Академии Наук filed Critical Федеральное Государственное Бюджетное Учреждение Науки Институт Химии Коми Научного Центра Уральского Отделения Российской Академии Наук
Publication of WO2013006098A2 publication Critical patent/WO2013006098A2/fr
Publication of WO2013006098A3 publication Critical patent/WO2013006098A3/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
    • C07C215/46—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C07C215/48—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups
    • C07C215/52—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups linked by carbon chains having two carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
    • C07C215/46—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C07C215/48—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups
    • C07C215/54—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups linked by carbon chains having at least three carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
    • C07C39/17—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings containing other rings in addition to the six-membered aromatic rings, e.g. cyclohexylphenol
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
    • C07C2602/42—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing seven carbon atoms

Definitions

  • the invention relates to space-hindered phenols, namely to terpenophenols, and more specifically, to functional derivatives of isobornylphenol.
  • the group of compounds represented by formula (I) isobornylphenol.
  • isobornyl moieties have the configuration (IS, 2R, 4R, VR, 2'S, 4'S) or (IS, 2R, 4R, l'S, TR, 4'R) and (IR, 2S, 4S VR, TS, 4'S).
  • Ri represents a group of the general formula II - (CH 2 ) n NX 2 , where X is the C1-C8 alkyl radical linear or branched, cyclohexyl, morpholine, piperidine, benzyl, salsolidine, salsoline, M-benzyl-1- phenylethylamine
  • n 1-30.
  • isobornyl fragments have the configuration (IS, 2R, 4R, VR, 2'S, 4'S) or (IS, 2R, 4R, 1 'S, TR, 4'R) and ( ⁇ R, 2S, 4S 1' D, 2'S, 4'S).
  • isobornyl fragments have the configuration (IS, 2R, 4R, VR, 2'S, 4'S) or (IS,
  • Ri is a formyl group
  • n l-30.
  • the aim of the invention is to obtain derivatives of 2,6-diisobornylphenol.
  • inventive compounds are synthesized by standard Mannich aminomethylation, bromomethylation, oxidation and reduction procedures.
  • Example 1 4-Hydroxy-3,5-bis (1, 7,7-trimethylbicyclo [2.2.1] hept-exo-2-yl) benzaldehyde, a colorless powder, so pl. 233-235 ° C.
  • the compound was obtained by a known method [V.V. Ershov, A. A. Volodkin, G. A. Nikiforov, K. M. Dyumaev. Sterically hindered phenols. Bromination of 2,6-dialkyl-p-cresols and 2,6-dialkyl-4- (bromomethyl) phenols // Russian Chemical Bulletin. 1962. Volume 11. No. 10. P. 1744-1747].
  • Example 2 4-Bromomethyl-2,6-bis (1, 7,7-trimethylbicyclo [2.2.1] hept-exo-2-yl) phenol, obtained by the known method [A.A. Volodkin, VV Ershov. Sterically hindered phenols. Phenol-dienone rearrangement in the bromination of 2,4,6-trialkylphenols // Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya. - 1962. - No. 6. - pp. 1108-1111; Galvin M. Coppinger, Tod W. Campbell. Reaction between 2,6-di-t-butyl-p-cresol and bromine. - 1952].
  • NMR spectrum I3 C (CDC1 3 , 75 MHz, ⁇ , ppm): 12.41 (C-10, C-10 '); 14.04 (C-24); 16.29 (C-17); 20.32 (C-9, C-9 '); 21.44 (C-8, C-8 '); 22.63 (C-23); July 27 (C-22); 27.57 (C-5, C-5 '); 30.00 (S-21); 31.79 (C-20); 34.23 (C-3, C-3 '); 30.08 (C-6, C-6 '); 45.60 (C-2, C-2 '); 45.83 (C-4, C-4 '); 48.07 (C-7, C-7 '); 49.29 (C-19); 49.72 (C-1, C-D); 53.98 (C-18); 122.74, 128.93, 131.19 (C-11, C-13, C-15); 125.81, 127.95 (C-14, C-16); 152.10 (C-12).

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Cosmetics (AREA)
  • Hydrogenated Pyridines (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne des phénols à encombrement stérique et notamment des terpène-phénols et plus particulièrement des dérivés fonctionnels d'isobornyl phénol. Le groupe d'invention est représenté par la formule (I).
PCT/RU2012/000533 2011-07-06 2012-06-27 Dérivés de 2,6-diisobornyl phénol WO2013006098A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
RU2011127776 2011-07-06
RU2011127776/04A RU2575294C2 (ru) 2011-07-06 Производные 2,6-диизоборнилфенола

Publications (2)

Publication Number Publication Date
WO2013006098A2 true WO2013006098A2 (fr) 2013-01-10
WO2013006098A3 WO2013006098A3 (fr) 2013-04-11

Family

ID=47437597

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/RU2012/000533 WO2013006098A2 (fr) 2011-07-06 2012-06-27 Dérivés de 2,6-diisobornyl phénol

Country Status (1)

Country Link
WO (1) WO2013006098A2 (fr)

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1510302A (en) * 1974-04-11 1978-05-10 Mar Pha Etu Expl Marques Terpenophenols

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
CHUKICHEVA, IRINA YUREVNA ET AL.: 'Alkilirovanie fenola kamfenom v prisutstvii venolyata aliuminiya. Khimiya i kompyuternoe modelirovanie.' BUTLEROVSKIE SOOBSHCHENIIA no. 1, 2003, pages 9 - 13 *
I.YU. CHUKICHEVA ET AL.: 'Issledovanie alkilirovaniia p-krezola kamfenom v prisutstvii kislotnykh katalizatorov.' KHIMIYA RASTITELNOGO SYRYA vol. 3, 2009, pages 63 - 68 *

Also Published As

Publication number Publication date
WO2013006098A3 (fr) 2013-04-11
RU2011127776A (ru) 2013-01-20

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