CN102482209B - 二取代的-氨基二氟亚硫鎓盐、其制备方法以及作为去氧氟化试剂的使用方法 - Google Patents

二取代的-氨基二氟亚硫鎓盐、其制备方法以及作为去氧氟化试剂的使用方法 Download PDF

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CN102482209B
CN102482209B CN201080027334.8A CN201080027334A CN102482209B CN 102482209 B CN102482209 B CN 102482209B CN 201080027334 A CN201080027334 A CN 201080027334A CN 102482209 B CN102482209 B CN 102482209B
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tetrafluoroborate
mmol
deoxyfluorination
dichloromethane
disubstituted
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CN102482209A (zh
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米歇尔·库蒂里耶
亚历山大·勒赫
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Omegachem Inc
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Omegachem Inc
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
    • C07C381/10—Compounds containing sulfur atoms doubly-bound to nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/76—Nitrogen atoms to which a second hetero atom is attached
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B39/00—Halogenation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
    • C07C17/16—Preparation of halogenated hydrocarbons by replacement by halogens of hydroxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
    • C07C17/18—Preparation of halogenated hydrocarbons by replacement by halogens of oxygen atoms of carbonyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/58—Preparation of carboxylic acid halides
    • C07C51/60—Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/307—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of halogen; by substitution of halogen atoms by other halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/06—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with radicals, containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/46—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with hetero atoms directly attached to the ring nitrogen atom
    • C07D207/48—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
    • C07D295/26—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/13—Crystalline forms, e.g. polymorphs
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pyridine Compounds (AREA)
  • Saccharide Compounds (AREA)
CN201080027334.8A 2009-06-19 2010-06-18 二取代的-氨基二氟亚硫鎓盐、其制备方法以及作为去氧氟化试剂的使用方法 Expired - Fee Related CN102482209B (zh)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US21859209P 2009-06-19 2009-06-19
US61/218,592 2009-06-19
US24770309P 2009-10-01 2009-10-01
US61/247,703 2009-10-01
PCT/CA2010/000959 WO2010145037A1 (en) 2009-06-19 2010-06-18 Disubstituted-aminodifluorosulfinium salts, process for preparing same and method of use as deoxofluorination reagents

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CN102482209A CN102482209A (zh) 2012-05-30
CN102482209B true CN102482209B (zh) 2014-08-20

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CN201080027334.8A Expired - Fee Related CN102482209B (zh) 2009-06-19 2010-06-18 二取代的-氨基二氟亚硫鎓盐、其制备方法以及作为去氧氟化试剂的使用方法

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US (1) US8680332B2 (enExample)
EP (1) EP2443087B1 (enExample)
JP (1) JP2012530075A (enExample)
KR (1) KR20120046718A (enExample)
CN (1) CN102482209B (enExample)
CA (1) CA2764241C (enExample)
WO (1) WO2010145037A1 (enExample)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2764241C (en) 2009-06-19 2016-03-08 Omegachem Inc. Disubstituted-aminodifluorosulfinium salts, process for preparing same and method of use as deoxofluorination reagents
CN107074899A (zh) * 2014-10-31 2017-08-18 桑多斯股份公司 改进的氟化工艺
EP4610245A1 (en) * 2022-10-25 2025-09-03 Agc Inc. Fluorine-containing compound production method
CN117447299A (zh) * 2023-10-31 2024-01-26 凯莱英医药化学（阜新）技术有限公司 偕二氟代化合物的合成方法
CN119654036B (zh) * 2024-12-13 2026-03-03 福州大学 一种具有均匀吸收层组分梯度的硫硒化锑太阳电池的制备方法

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0905109A1 (en) * 1997-09-29 1999-03-31 Air Products And Chemicals, Inc. Fluorination with aminosulfur trifluorides
EP1095934A1 (en) * 1999-11-01 2001-05-02 Air Products And Chemicals, Inc. Process for the synthesis of dialkyl, diaryl, and arylalkyl aminosulphur trifluorides
EP1172369A1 (en) * 2000-07-13 2002-01-16 Air Products And Chemicals, Inc. Synthesis of 2-deoxy-2-fluoro-arabinose derivates
CN1720256A (zh) * 2002-12-04 2006-01-11 三菱瓦斯化学株式会社 氟化方法
CN1762971A (zh) * 2005-11-07 2006-04-26 上海泰卓科技有限公司 一种含氟酰氟类化合物的新处理方法

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5389708A (en) * 1992-01-31 1995-02-14 Mitsui Toatsu Chemicals, Inc. Sulfur-containing acid phosphoric ester internal release agent
EP1892231A1 (en) * 2006-08-21 2008-02-27 Bayer Schering Pharma Aktiengesellschaft A large scale method for the deoxofluorination of ketones
CA2764241C (en) 2009-06-19 2016-03-08 Omegachem Inc. Disubstituted-aminodifluorosulfinium salts, process for preparing same and method of use as deoxofluorination reagents

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0905109A1 (en) * 1997-09-29 1999-03-31 Air Products And Chemicals, Inc. Fluorination with aminosulfur trifluorides
EP1095934A1 (en) * 1999-11-01 2001-05-02 Air Products And Chemicals, Inc. Process for the synthesis of dialkyl, diaryl, and arylalkyl aminosulphur trifluorides
EP1172369A1 (en) * 2000-07-13 2002-01-16 Air Products And Chemicals, Inc. Synthesis of 2-deoxy-2-fluoro-arabinose derivates
CN1720256A (zh) * 2002-12-04 2006-01-11 三菱瓦斯化学株式会社 氟化方法
CN1762971A (zh) * 2005-11-07 2006-04-26 上海泰卓科技有限公司 一种含氟酰氟类化合物的新处理方法

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
dialkylaminodifluorosulfonium tetrafluoroborates;L.N.Markovskii等;《Zhurnal Organicheskoi Khimii》;19771231;第13卷;第1116页化学反应式及第1117页第二段具体化合物的表征 *
L.N.Markovskii等.dialkylaminodifluorosulfonium tetrafluoroborates.《Zhurnal Organicheskoi Khimii》.1975,第40卷(第5期),第1116页化学反应式及第1117页第二段具体化合物的表征. *
NewFluorinating Reagents.Dialkylaminosulfur Fluorides;William J.Middleton;《J.Org.Chem.》;19751231;第40卷(第5期);第574页制备 *

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EP2443087A4 (en) 2012-12-05
JP2012530075A (ja) 2012-11-29
US8680332B2 (en) 2014-03-25
CA2764241A1 (en) 2010-12-23
CA2764241C (en) 2016-03-08
US20120108801A1 (en) 2012-05-03
WO2010145037A1 (en) 2010-12-23
CN102482209A (zh) 2012-05-30
EP2443087A1 (en) 2012-04-25
EP2443087B1 (en) 2016-06-08
KR20120046718A (ko) 2012-05-10

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