CA2035029A1 - Synthesis of stable water-soluble chemiluminescent 1,2-dioxetanes and intermediates therefor - Google Patents

Synthesis of stable water-soluble chemiluminescent 1,2-dioxetanes and intermediates therefor

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Publication number
CA2035029A1
CA2035029A1 CA002035029A CA2035029A CA2035029A1 CA 2035029 A1 CA2035029 A1 CA 2035029A1 CA 002035029 A CA002035029 A CA 002035029A CA 2035029 A CA2035029 A CA 2035029A CA 2035029 A1 CA2035029 A1 CA 2035029A1
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Prior art keywords
formula
group
synthesis
aryl
dioxetanes
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CA002035029A
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French (fr)
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CA2035029C (en
Inventor
Brooks Edwards
Rouh-Rong Juo
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Applied Biosystems LLC
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Individual
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Priority to CA002340484A priority Critical patent/CA2340484C/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
    • C07C43/14—Unsaturated ethers
    • C07C43/17—Unsaturated ethers containing halogen
    • C07C43/174—Unsaturated ethers containing halogen containing six-membered aromatic rings
    • C07C43/1747—Unsaturated ethers containing halogen containing six-membered aromatic rings containing six membered aromatic rings and other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
    • C07C45/292—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups with chromium derivatives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
    • C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
    • C07C47/575—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D321/00—Heterocyclic compounds containing rings having two oxygen atoms as the only ring hetero atoms, not provided for by groups C07D317/00 - C07D319/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/40—Esters thereof
    • C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4056—Esters of arylalkanephosphonic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
    • C07F9/6551—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a four-membered ring
    • C07F9/65512—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a four-membered ring condensed with carbocyclic rings or carbocyclic ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
    • C07F9/65515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a five-membered ring
    • C07F9/65517—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a five-membered ring condensed with carbocyclic rings or carbocyclic ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
    • C07F9/6552—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a six-membered ring
    • C07F9/65522—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a six-membered ring condensed with carbocyclic rings or carbocyclic ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/56—Ring systems containing bridged rings
    • C07C2603/58—Ring systems containing bridged rings containing three rings
    • C07C2603/70—Ring systems containing bridged rings containing three rings containing only six-membered rings
    • C07C2603/74—Adamantanes

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

A novel synthesis of compounds having the formula:
(See formula I) wherein T is a stabilizing spiro-linked polycycloalkyli-dene group, R3 is a C1-C20 alkyl, aralkyl or heteroatom containing group, Y is an aromatic fluorescent chromo-phore, and Z is a cleavable group which, when cleaved, induces decomposition of the dioxetane ring and emission of optically detectable light, is disclosed. A tertiary phosphorous acid alkyl ester of the formula:
(R1O)3P
wherein R1 is a lower alkyl group, is reacted with an aryl dialkyl acetal produced by reacting a corresponding aryl aldehyde with an alcohol of the formula:

wherein R3 is as defined above, to produce a 1-alkoxy-1-aryl-methane phosphonate ester of the formula:
(See formula II)
CA002035029A 1989-09-06 1990-09-04 Synthesis of stable water-soluble chemiluminescent 1,2-dioxetanes and intermediates therefor Expired - Lifetime CA2035029C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CA002340484A CA2340484C (en) 1989-09-06 1990-09-04 Synthesis of stable water-soluble chemiluminescent 1,2-dioxetanes and intermediates therefor

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US40284789A 1989-09-06 1989-09-06
US57478990A 1990-08-30 1990-08-30
US574,784 1990-08-30
PCT/US1990/004919 WO1991003479A1 (en) 1989-09-06 1990-09-04 Synthesis of stable, water-soluble chemiluminescent 1,2-dioxetanes and intermediates therefor
US402,847 1990-09-06

Related Child Applications (1)

Application Number Title Priority Date Filing Date
CA002340484A Division CA2340484C (en) 1989-09-06 1990-09-04 Synthesis of stable water-soluble chemiluminescent 1,2-dioxetanes and intermediates therefor

Publications (2)

Publication Number Publication Date
CA2035029A1 true CA2035029A1 (en) 1991-03-07
CA2035029C CA2035029C (en) 2001-12-18

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Family Applications (1)

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CA002035029A Expired - Lifetime CA2035029C (en) 1989-09-06 1990-09-04 Synthesis of stable water-soluble chemiluminescent 1,2-dioxetanes and intermediates therefor

Country Status (3)

Country Link
EP (1) EP0441948A4 (en)
CA (1) CA2035029C (en)
WO (1) WO1991003479A1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN116380854A (en) * 2023-03-06 2023-07-04 上海电力大学 Method for rapidly detecting microplastic pollution in water based on fluorescence spectrum

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6251581B1 (en) * 1991-05-22 2001-06-26 Dade Behring Marburg Gmbh Assay method utilizing induced luminescence
DE69233674T2 (en) * 1991-05-22 2007-10-18 Dade Behring Marburg Gmbh Homogeneous test system for the determination of an analyte
US5578498A (en) 1991-05-22 1996-11-26 Behringwerke Ag Metal chelate containing compositions for use in chemiluminescent assays
CA2170873A1 (en) * 1993-09-03 1995-03-09 Dariush Davalian Fluorescent oxygen channeling immunoassays
US5731445A (en) * 1995-12-04 1998-03-24 Fujirebio Inc. 1,2- Dioxetane derivatives
US11312873B2 (en) * 2019-09-04 2022-04-26 Eastman Chemical Company Aromatic enol ether paint additives
CN117964661B (en) * 2024-04-01 2024-06-07 深圳创元生物医药科技有限公司 Preparation method of fosfomycin genotoxic impurity C

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL8201492A (en) * 1982-04-07 1983-11-01 Rijksuniversiteit PROCESS FOR PREPARING A 4-PLACE EQUATORALLY SUBSTITUTED SYMMETRICAL-POLYCYCLETHYLENE COMPOUND; SYMMETRICAL-POLYCYCLETHYLENE COMPOUND SUBSTITUTED IN THE 4-PLACE EQUATORALLY COMPOSITION AND A THERMOCHEMILUMINUM SCREENING PROCESS MATERIAL PREPARED ON THE BASIS OF THE COMPOUND.
US4857652A (en) * 1986-07-17 1989-08-15 Board Of Governors Of Wayne State University Chemiluminescent 1,2-dioxetane compounds
US4956477A (en) * 1987-12-31 1990-09-11 Tropix, Inc. Synthesis of 1,2-dioxetanes
DE3788203T2 (en) * 1986-07-24 1994-03-31 Tropix Inc METHOD FOR DETECTING A CONNECTION USING THE ENZYMATICALLY INDUCED DECOMPOSITION OF DIOXETHANES.
JPH0731201B2 (en) * 1987-12-31 1995-04-10 トロピックス・インコーポレーテッド Chemiluminescence measurement method
US4952707A (en) * 1988-06-30 1990-08-28 Tropix, Inc. Enzymatically-cleavable chemiluminescent fused polycyclic ring-containing 1,2-dioxetanes

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN116380854A (en) * 2023-03-06 2023-07-04 上海电力大学 Method for rapidly detecting microplastic pollution in water based on fluorescence spectrum
CN116380854B (en) * 2023-03-06 2025-05-30 上海电力大学 Method for rapidly detecting microplastic pollution in water based on fluorescence spectrum

Also Published As

Publication number Publication date
EP0441948A4 (en) 1992-06-03
EP0441948A1 (en) 1991-08-21
WO1991003479A1 (en) 1991-03-21
CA2035029C (en) 2001-12-18

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