Title:
1,6-DIYNE COMPOUND AND PREPARATION METHOD THEREFOR, AND PRODUCT OBTAINED USING 1,6-DIYNE COMPOUND AS RAW MATERIAL AND USE THEREOF
Document Type and Number:
WIPO Patent Application WO/2023/165217
Kind Code:
A1
Abstract:
Disclosed in the present application are a 1,6-diyne compound and a preparation method therefor, a product obtained using the 1,6-diyne compound as a raw material and the use thereof, which belong to the field of organic synthesis. A compound shown in general formula (I), and a tautomer, polymorph, solvate or salt thereof, i.e., the 1,6-diyne compound provided in the present application, have changeable structures and convenient synthesis, and are suitable for industrial production, and the use thereof in the synthesis of a benzisoindole dimer compound and a derivative thereof, cell imaging, and the detection of active oxygen (sodium hypochlorite, hydrogen peroxide, and ozone, etc.). A 3-arylbenzoisoindole compound provided in the present application can play an important role as an important compound in drugs or fluorescent materials.
Inventors:
BAO HONGLI (CN)
YE CHANGQING (CN)
HUANG RUI (CN)
ZHU NENGBO (CN)
YE CHANGQING (CN)
HUANG RUI (CN)
ZHU NENGBO (CN)
Application Number:
PCT/CN2022/138827
Publication Date:
September 07, 2023
Filing Date:
December 13, 2022
Export Citation:
Assignee:
FUJIAN INSTITUTE OF RES ON THE STRUCTURE OF MATTER CHINESE ACADEMY OF SCIE (CN)
International Classes:
C07C311/16; C07D209/62; C07D209/56; C07D209/58; C09K9/02; G01N21/25
Foreign References:
| CN109574913A | 2019-04-05 | |||
| CN106513049A | 2017-03-22 | |||
| CN113372392A | 2021-09-10 |
Other References:
LIU RUIXING, WANG QIANG, WEI YIN, SHI MIN: "Synthesis of indolizine derivatives containing eight-membered rings via a gold-catalyzed two-fold hydroarylation of diynes", CHEMICAL COMMUNICATIONS, ROYAL SOCIETY OF CHEMISTRY, UK, vol. 54, no. 10, 1 January 2018 (2018-01-01), UK , pages 1225 - 1228, XP093088473, ISSN: 1359-7345, DOI: 10.1039/C7CC09250D
YI XIAOFEI, CHEN KAI, CHEN WEI, CHEN WANZHI, LIU MIAOCHANG, WU HUAYUE: "Synthesis of cyclic gem -dinitro compounds via radical nitration of 1,6-diynes with Fe(NO 3 ) 3 ·9H 2 O", ORGANIC & BIOMOLECULAR CHEMISTRY, ROYAL SOCIETY OF CHEMISTRY, vol. 17, no. 19, 15 May 2019 (2019-05-15), pages 4725 - 4728, XP093088475, ISSN: 1477-0520, DOI: 10.1039/C9OB00431A
SHAINYAN B. A.: "Mono- and disubstituted highly unsaturated trifluoromethanesulfonamide derivatives. Theoretical analysis", RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, M A I K NAUKA - INTERPERIODICA, RU, vol. 51, no. 5, 1 May 2015 (2015-05-01), RU , pages 605 - 609, XP093088477, ISSN: 1070-4280, DOI: 10.1134/S1070428015050024
YASUI TAKESHI, TATSUMI RINE, YAMAMOTO YOSHIHIKO: "Highly Enantioselective [2+2+2] Cycloaddition of Enediynes Enabled by Cobalt/Organophotoredox Cooperative Catalysis", ACS CATALYSIS, AMERICAN CHEMICAL SOCIETY, US, vol. 11, no. 15, 6 August 2021 (2021-08-06), US , pages 9479 - 9484, XP093088478, ISSN: 2155-5435, DOI: 10.1021/acscatal.1c02410
SCHWARTZ BRETT D., BOOTH YVONNE K., FLETCHER MARY T., KITCHING WILLIAM, DE VOSS JAMES J.: "Spiroacetal biosynthesis in fruit flies is complex: distinguishable origins of the same major spiroacetal released by different Bactrocera spp.", CHEMICAL COMMUNICATIONS, ROYAL SOCIETY OF CHEMISTRY, UK, vol. 46, no. 9, 1 January 2010 (2010-01-01), UK , pages 1526, XP093088479, ISSN: 1359-7345, DOI: 10.1039/b917977a
REMY DAVID E., BISSETT FRANK H.: "Benz[f]isoindole", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, vol. 43, no. 23, 1 November 1978 (1978-11-01), pages 4469 - 4472, XP093088482, ISSN: 0022-3263, DOI: 10.1021/jo00417a016
DATABASE Registry 23 February 2022 (2022-02-23), "1H-Naphtho[2',3':2,3][1,4]benzodioxino[6,7-f]isoindole (CA INDEX NAME)", XP093088492, retrieved from STNext Database accession no. 2760451-86-1
SEIKE AYA, YAMAGAMI KAORU, KAKITANI YOSHIMASA, KUWAJIMA MIKI, UOYAMA HIROKI, NAGAOKA SHIN-ICHI, NAKAE TAKAHIRO, MORI SHIGEKI, OKUJ: "Synthesis, structure and properties of ethyl naphth[2,3-f]isoindole-1-carboxylate", RSC ADVANCES, vol. 3, no. 9, 1 January 2013 (2013-01-01), pages 3006, XP093088486, DOI: 10.1039/c2ra22870j
LIU RUIXING, WANG QIANG, WEI YIN, SHI MIN: "Synthesis of indolizine derivatives containing eight-membered rings via a gold-catalyzed two-fold hydroarylation of diynes", CHEMICAL COMMUNICATIONS, ROYAL SOCIETY OF CHEMISTRY, UK, vol. 54, no. 10, 1 January 2018 (2018-01-01), UK , pages 1225 - 1228, XP093088473, ISSN: 1359-7345, DOI: 10.1039/C7CC09250D
YI XIAOFEI, CHEN KAI, CHEN WEI, CHEN WANZHI, LIU MIAOCHANG, WU HUAYUE: "Synthesis of cyclic gem -dinitro compounds via radical nitration of 1,6-diynes with Fe(NO 3 ) 3 ·9H 2 O", ORGANIC & BIOMOLECULAR CHEMISTRY, ROYAL SOCIETY OF CHEMISTRY, vol. 17, no. 19, 15 May 2019 (2019-05-15), pages 4725 - 4728, XP093088475, ISSN: 1477-0520, DOI: 10.1039/C9OB00431A
ROBERT W. FOSTER; CHRISTOPHER J. TAME; HELEN C. HAILES; TOM D. SHEPPARD: "Highly Regioselective Synthesis of Substituted Isoindolinones via Ruthenium‐Catalyzed Alkyne Cyclotrimerizations", ADVANCED SYNTHESIS AND CATALYSIS, JOHN WILEY & SONS, INC., HOBOKEN, USA, vol. 355, 12 August 2013 (2013-08-12), Hoboken, USA, pages 2353 - 2360, XP072486106, ISSN: 1615-4150, DOI: 10.1002/adsc.201300055
YI XIAOFEI, CHEN KAI, CHEN WEI, CHEN WANZHI, LIU MIAOCHANG, WU HUAYUE: "Synthesis of cyclic gem -dinitro compounds via radical nitration of 1,6-diynes with Fe(NO 3 ) 3 ·9H 2 O", ORGANIC & BIOMOLECULAR CHEMISTRY, ROYAL SOCIETY OF CHEMISTRY, vol. 17, no. 19, 15 May 2019 (2019-05-15), pages 4725 - 4728, XP093088475, ISSN: 1477-0520, DOI: 10.1039/C9OB00431A
SHAINYAN B. A.: "Mono- and disubstituted highly unsaturated trifluoromethanesulfonamide derivatives. Theoretical analysis", RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, M A I K NAUKA - INTERPERIODICA, RU, vol. 51, no. 5, 1 May 2015 (2015-05-01), RU , pages 605 - 609, XP093088477, ISSN: 1070-4280, DOI: 10.1134/S1070428015050024
YASUI TAKESHI, TATSUMI RINE, YAMAMOTO YOSHIHIKO: "Highly Enantioselective [2+2+2] Cycloaddition of Enediynes Enabled by Cobalt/Organophotoredox Cooperative Catalysis", ACS CATALYSIS, AMERICAN CHEMICAL SOCIETY, US, vol. 11, no. 15, 6 August 2021 (2021-08-06), US , pages 9479 - 9484, XP093088478, ISSN: 2155-5435, DOI: 10.1021/acscatal.1c02410
SCHWARTZ BRETT D., BOOTH YVONNE K., FLETCHER MARY T., KITCHING WILLIAM, DE VOSS JAMES J.: "Spiroacetal biosynthesis in fruit flies is complex: distinguishable origins of the same major spiroacetal released by different Bactrocera spp.", CHEMICAL COMMUNICATIONS, ROYAL SOCIETY OF CHEMISTRY, UK, vol. 46, no. 9, 1 January 2010 (2010-01-01), UK , pages 1526, XP093088479, ISSN: 1359-7345, DOI: 10.1039/b917977a
REMY DAVID E., BISSETT FRANK H.: "Benz[f]isoindole", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, vol. 43, no. 23, 1 November 1978 (1978-11-01), pages 4469 - 4472, XP093088482, ISSN: 0022-3263, DOI: 10.1021/jo00417a016
DATABASE Registry 23 February 2022 (2022-02-23), "1H-Naphtho[2',3':2,3][1,4]benzodioxino[6,7-f]isoindole (CA INDEX NAME)", XP093088492, retrieved from STNext Database accession no. 2760451-86-1
SEIKE AYA, YAMAGAMI KAORU, KAKITANI YOSHIMASA, KUWAJIMA MIKI, UOYAMA HIROKI, NAGAOKA SHIN-ICHI, NAKAE TAKAHIRO, MORI SHIGEKI, OKUJ: "Synthesis, structure and properties of ethyl naphth[2,3-f]isoindole-1-carboxylate", RSC ADVANCES, vol. 3, no. 9, 1 January 2013 (2013-01-01), pages 3006, XP093088486, DOI: 10.1039/c2ra22870j
LIU RUIXING, WANG QIANG, WEI YIN, SHI MIN: "Synthesis of indolizine derivatives containing eight-membered rings via a gold-catalyzed two-fold hydroarylation of diynes", CHEMICAL COMMUNICATIONS, ROYAL SOCIETY OF CHEMISTRY, UK, vol. 54, no. 10, 1 January 2018 (2018-01-01), UK , pages 1225 - 1228, XP093088473, ISSN: 1359-7345, DOI: 10.1039/C7CC09250D
YI XIAOFEI, CHEN KAI, CHEN WEI, CHEN WANZHI, LIU MIAOCHANG, WU HUAYUE: "Synthesis of cyclic gem -dinitro compounds via radical nitration of 1,6-diynes with Fe(NO 3 ) 3 ·9H 2 O", ORGANIC & BIOMOLECULAR CHEMISTRY, ROYAL SOCIETY OF CHEMISTRY, vol. 17, no. 19, 15 May 2019 (2019-05-15), pages 4725 - 4728, XP093088475, ISSN: 1477-0520, DOI: 10.1039/C9OB00431A
ROBERT W. FOSTER; CHRISTOPHER J. TAME; HELEN C. HAILES; TOM D. SHEPPARD: "Highly Regioselective Synthesis of Substituted Isoindolinones via Ruthenium‐Catalyzed Alkyne Cyclotrimerizations", ADVANCED SYNTHESIS AND CATALYSIS, JOHN WILEY & SONS, INC., HOBOKEN, USA, vol. 355, 12 August 2013 (2013-08-12), Hoboken, USA, pages 2353 - 2360, XP072486106, ISSN: 1615-4150, DOI: 10.1002/adsc.201300055
Attorney, Agent or Firm:
PERIODIC LAW FIRM (CN)
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