CAS: 624-75-9; 2-Iodoacetonitrile

该化合物是有机化学中广泛使用的多用途烷基剂和合成中间体.这种无色的黄色液体因其高反应性高而具有价值,特别是在核生殖替代和循环反应方面.它的碘能提高电益性,使其有利于在精细化学合成中引入丙乙基组.Iodoacetonitrile通常用于制作异性循环,制药和农用化学品.它需要谨慎处理,因为它的乳胶特性和湿度敏感度.在惰性条件下,它提供迈克尔添加和碳链延伸等反应的一贯性能.它的平衡性能和稳定性使它成为复杂分子结构中受控功能化的实际选择.

结构式图片

相似化合物

144-48-9 2517-76-2 1219802-64-8

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合成工艺路线路线简述

  • 合成目标产物 Iodoacetonitrile 主要起始原料 Bromoacetonitrile
  • (文献来源)合成步骤主要原料 Bromoacetonitrile
氟乙腈置于lithium Iodide体系中,用 Neat (No Solvent) 作为反应溶剂,化学反应 18.0H,以97%的收率获得产物碘乙腈
参考文献:用碘化锂选择性 Csp3-f 键功能化
标题:用碘化锂选择性 Csp3-f 键功能化
摘要:提出了一种使用廉价的碘化锂对各种活化和未活化脂肪族基材进行 C-F 键功能化的高效方法.伯,仲,叔,苄基,炔丙基和α-官能化烷基氟化物在氯化或芳香族溶剂中在室温或加热下反应反应生成相应的碘化物,其分离收率为91-99%.该反应对脂肪族一氟化物具有选择性,并且可以与原位亲核碘化物取代偶联,以高产率安装碳-碳,碳-氮和碳-硫键.烷基二氟化物,三氟化物,即使在活化的苄基位置,在相同条件下也是惰性的,并且也可以容忍芳基氟化物键.
DOI:10.1055/s-0041-1738383

海关参考信息

专利信息


专利号:US-5840915-A
优先权日:1990-01-22
标题:Process for the enatioselective synthesis of intermediates used
发明人:LEE THOMAS BING KIN; WONG GEORGE SEUNG-KIT
权利人:HOECHST MARION ROUSSEL INC
摘要:A process for the stereoselective synthesis of [R]- and [S]-2,3-dihydro-1,3-dimethyl-2-oxo-1H-indole-3-acetonitriles comprises reacting racemic and 5-alkoxy-substituted (+/-)-1,3-dimethyloxindoles with a halogenated acetonitrile in the presence of a substituted N-benzyl cinchoninium, quinidinium, cinchonidinium, or quininium catalyst. The resulting alkylated oxindoles can be converted to primary amines by catalytic reduction in the presence of hydrogen gas. One of the primary amines, such as enantiomers of 3-(2-aminoethyl)-1,3-dihydro-1,3-dimethyl-5-methoxy-2H-indol-2-one, can be enriched by contact with a chiral tartaric acid in an amount sufficient to preferentially precipitate a salt of the chiral acid and one of the enantiomers. The product can be used in the synthesis of stereospecific forms of physostigmine and related compounds having pharmaceutical activity.

专利号:US-5274117-A
优先权日:1990-01-22
标 题:Process for the enantioselective synthesis of intermediates used in the preparation of physostigmine
发明人:LEE THOMAS BING KIN DR; WONG GEORGE S K
权利人:HOECHST ROUSSEL PHARMA
摘要:A process for the stereoselective synthesis of [R]- and [S]-2,3-dihydro-1,3-dimethyl-2-oxo-1H-indole-3-acetonitriles comprises reacting racemic and 5-alkoxy-substituted (+/-)-1,3-dimethyloxindoles with a halogenated acetonitrile in the presence of a substituted N-benzyl cinchoninium, quinidinium, cinchonidinium, or quininium catalyst. The resulting alkylated oxindoles can be converted to primary amines by catalytic reduction in the presence of hydrogen gas. One of the primary amines, such as enantiomers of 3-(2-aminoethyl)-1,3-dihydro-1,3-dimethyl-5-methoxy-2H-indol-2-one, can be enriched by contact with a chiral tartaric acid in an amount sufficient to preferentially precipitate a salt of the chiral acid and one of the enantiomers. The product can be used in the synthesis of stereospecific forms of physostigmine and related compounds having pharmaceutical activity.

专利号:EP-0438796-B1
优先权日:1990-01-22
标题:Process for the enantioselection synthesis of alkylated oxindoles used as intermediates in the preparation of physostigmine
发明人:LEE THOMAS BING KIN DR; WONG GEORGE S K
权利人:HOECHST MARION ROUSSEL INC
摘要:A process for the stereoselective synthesis of [R]- and [S]-2,3-dihydro-1,3-dimethyl-2-oxo-1H-indole-3-acetonitriles comprises reacting racemic and 5-alkoxy-substituted (+/-)-1,3-dimethyloxindoles with a halogenated acetonitrile in the presence of a substituted N-benzyl cinchoninium, quinidinium, cinchonidinium, or quininium catalyst. The resulting alkylated oxindoles can be converted to primary amines by catalytic reduction in the presence of hydrogen gas. One of the primary amines, such as enantiomers of 3-(2-aminoethyl)-1,3-dihydro-1,3-dimethyl-5-methoxy-2H-indol-2-one, can be enriched by contact with a chiral tartaric acid in an amount sufficient to preferentially precipitate a salt of the chiral acid and one of the enantiomers. The product can be used in the synthesis of stereospecific forms of physostigmine and related compounds having pharmaceutical activity.

专利号:US-2013165350-A1
优先权日:2011-12-22
标 题:Surface linkers for array synthesis
发明人:KUIMELIS ROBERT; MCGALL GLENN; PAO DEXTER; CHEN ZIHUI; AXELROD TREVOR
权利人:KUIMELIS ROBERT; MCGALL GLENN; PAO DEXTER; CHEN ZIHUI; AXELROD TREVOR; AFFYMETRIX INC
摘要:The present invention provide several methods of derivatizing a surface of a support with one or more linkers thus providing a suitable platform for synthesis of a polymer array, particular a nucleic acid array. Some methods derivatize a surface with a self-assembled monolayer (SAM) of a linker. The SAM confers advantages of hydrolytic stability, broad compatibility with synthesis and detection chemistries, and reduced emergence of latent functional groups during polymer array synthesis. Substrates can also be derivatized with multi-layers of SAMs providing greater hydrolytic stability. Substrates can also be derivatized by synthesizing a linker in situ on the substrate by atom transfer radical polymerization of functional and functional monomers. Appropriate selection of monomers reduces emergence of latent functional groups in subsequent array synthesis.

专利号:US-9512250-B2
优先权日:2012-02-23
标 题 :Manganese catalyzed photopolymerization of fluorinated monomers
发明人:ASANDEI ALEXANDRU D
权利人:UNIV CONNECTICUT
摘要:The disclosure discloses initiating systems for the radical polymerization of alkenes, and especially fluorine substituted alkenes. The polymerization is catalyzed by a metal carbonyl, preferably manganese carbonyl. The polymerization is initiated directly from alkyl halides at room temperature under visible white light. The polymers also allow the synthesis of block copolymers. The process comprises polymerizing at least one alkene monomer in the presence of a halide radical initiator, carbonyl catalyst and a solvent, under reaction conditions and for a time sufficient to polymerize the at least one alkene monomer to form a polymer. The present disclosure provides a method for living polymerization of alkene monomers which provides a high level of macromolecular control over the polymerization process and which leads to uniform and controllable polymeric products. This disclosure also provides a method for activating any halide (Cl, Br, I) chain ends of such polymers for the synthesis of block copolymerizations.

专利号:US-11512097-B2
优先权日:2019-11-25
标题 :Heterocyclic compounds as Delta-5 desaturase inhibitors and methods of use
发明人:ALLEN JENNIFER R; BELTRANI MICHELA; BOURBEAU MATTHEW P; DAMYANOVA TEODORA P; LINGARD IAIN; MINATTI ANA E; VINCETTI PAOLO
权利人:AMGEN INC
摘要:The present disclosure provides compounds useful for the inhibition of Delta-5 Desaturase (“D5Dâ€?). The compounds have a general Formula I n nwherein the variables of Formula I are defined herein. This disclosure also provides pharmaceutical compositions comprising the compounds, uses of the compounds, and compositions for treatment of, for example, a metabolic or cardiovascular disorder. Further, the disclosure provides intermediates useful in the synthesis of compounds of Formula I.
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合成参考文献


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摘要:Fusano, A.; Ryu, I., Science of Synthesis: Multicomponent Reactions, (2013) 2, 427.
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