CAS: 485-71-2; Cinchonidine

该化合物是一种来自辛索纳树树树皮的碱性碱,主要以其用于治疗疟疾和有机合成中作为手性辅助剂而闻名;其分子配方为C18H21N,其结构具有双环肾素系统,有助于其药理特性;辛索尼丁是一种白色的,非白晶体固体,具有典型的苦味;它展示了光学活动,在非对称合成中具有价值;该化合物溶于乙醇和氯仿等有机溶剂,但水溶性有限;其药理效应包括抗疟活动,并且已经研究过其作为当地...

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118-10-5 524-63-0 485-64-3

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Cinchonin pentan-1-ol O-tosylcinchonidine methanesulfonic acid (quinolin-4-yl)(5-vinyl-1-azabicyclo[2.2.2]°Ct-2-yl)methyl ester(4S,5R)-1,3-dibenzyl-5-formyl-2-oxo-4-imidazolidine carboxylic acid cinchonidine salt imidazole-2,4-dione(3aR,6S,6aS)-1,3-dibenzyl-6-hydroxy-3,3a,6,6a-tetrahydro-1H-furo3,4-dimidazole-2,4-dione (R)-1-Ethoxymethyl-2,6-dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid monomethyl ester; compound with (S)-quinolin-4-yl-((1S,2S,4S,5R)-5-vinyl-1-aza-bicyclo[2.2.2]°Ct-2-yl)-methanol (R)-1-Ethoxymethyl-2,6-dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid monomethyl ester; compound with (S)-quinolin-4-yl-((1S,2S,4S,5R)-5-vinyl-1-aza-bicyclo[2.2.2]°Ct-2-yl)-methanol

合成工艺路线路线简述

    Alkaline Earth Salt Of/the/ Methylsulfuric Acid 反应生成 辛可尼丁
    参考文献:102.将氢奎尼丁转化为氢辛可宁,将铜脲转化为辛可尼定
    标题:102.将氢奎尼丁转化为氢辛可宁,将铜脲转化为辛可尼定
    摘要:
    DOI:10.1039/jr9460000523

    海关参考信息

    专利信息


    专利号:US-7323575-B2
    优先权日:2003-04-09
    标题:Process for the synthesis of (2S)-indoline-2-carboxylic acid
    发明人:SOUVIE JEAN-CLAUDE; LECOUVE JEAN-PIERRE
    权利人:SERVIER LAB
    摘要:Process for the synthesis of (2S)-indoline-2-carboxylic acid of formula (I): n nApplication in the synthesis of perindopril and its pharmaceutically acceptable salts.

    专利号:US-9126995-B2
    优先权日:2011-11-08
    标题:Method for catalytic asymmetric synthesis of optically active isoxazoline compound and optically active isoxazoline compound
    发明人:TOYAMA KEN-ICHI; MORIYAMA YUJI; MATOBA KAZUTAKA; YAOSAKA MANABU; IKEDA EITATSU
    权利人:NISSAN CHEMICAL IND LTD
    摘要:There is provided a method for catalytic asymmetric synthesis of optically active isoxazoline compound and an optically active isoxazoline compound. A method for catalytic asymmetric synthesis of optically active isoxazoline compound of a formula (6) including reacting an α,β-unsaturated carbonyl compound of a formula (1) and a hydroxylamine in a solvent in the presence of a base by adding a chiral phase transfer catalyst. An optically active isoxazoline compound of a formula (13) that can be synthesized by the method.

    专利号:US-6555686-B2
    优先权日:2000-03-23
    标题:Asymmetric synthesis of quinazolin-2-ones useful as HIV reverse transcriptase inhibitors
    发明人:PARSONS RODNEY L; DOROW ROBERTA L; DAVULCU AKIN H; FORTUNAK JOSEPH M; HARRIS GREGORY D; KAUFFMAN GOSS S; NUGENT WILLIAM A; RADESCA LILIAN A
    权利人:BRISTOL MYERS SQUIBB PHARMA
    摘要:This invention relates generally to the asymmetric synthesis of quinazolin-2-ones that are useful as inhibitors of HIV reverse transcriptase. The synthesis is accomplished through the chiral ligand mediated addition of cyclopropylacetylide.

    专利号:US-4190579-A
    优先权日:1977-12-29
    标题:Synthesis of beta-lactams from azetidine carboxylic acid esters
    发明人:LIPSHUTZ BRUCE H; WASSERMAN HARRY H; WU JAMES S
    权利人:RESEARCH CORP
    摘要:Azetidine carboxylic acid esters are converted into enol silyl ethers which, as enamino ketene acetals, undergo ready oxidative cleavage of the ethylenically unsaturated double bond, e.g. by dye-sensitized photo-oxygenation, to form beta-lactams. The beta-lactams and substitution products thereof are useful intermediates in the synthesis of biologically active lactams.

    专利号:US-8283502-B2
    优先权日:2009-04-09
    标题:Autocatalytic process for the synthesis of chiral propargylic alcohols
    发明人:CHINKOV NICKA; WARM ALEKSANDER; CARREIRA ERICK
    权利人:CHINKOV NICKA; WARM ALEKSANDER; CARREIRA ERICK; LONZA AG
    摘要:An autocatalytic process for the synthesis of chiral propargylic alcohols.

    专利号:WO-2012059797-A1
    优先权日:2010-11-04
    标题 :Process for synthesis of (s) - pregabalin
    发明人:ROY BHAIRAB NATH; SINGH GIRIJ PAL; LATHI PIYUSH SURESH; AGRAWAL MANOJ KUNJABIHARI; MITRA RANGAN; RUPNAWAR MANOJ DATTATRAYA
    权利人:LUPIN LTD; ROY BHAIRAB NATH; SINGH GIRIJ PAL; LATHI PIYUSH SURESH; AGRAWAL MANOJ KUNJABIHARI; MITRA RANGAN; RUPNAWAR MANOJ DATTATRAYA
    摘要:Improved process for the synthesis of (S)-pregabalin having more than 99% ee through (S) 3-cyano-5-methyl-hexanoic acid has been developed. In addition to above, a novel process for resolution of ( RS ) - 3-cyano-5-methyl-hexanoic acid through diastereomeric salt formation with cinchonidine to obtain ( S ) - 3-cyano-5-methyl-hexanoic acid in high yield and high optical purity has been developed and furthermore process for recovery/ reuse of cinchonidine is also developed to improve the overall process efficiency.
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    主要参考文献


    1: Deka J, Satyanarayana L, Karunakar GV, Bhattacharyya PK, Bania KK. Chiral modification of copper exchanged zeolite-Y with cinchonidine and its application in the asymmetric Henry reaction. Dalton Trans. 2015 Dec 28;44(48):20949-63. doi: 10.1039/c5dt03630e. Epub 2015 Nov 18. doi: 10.1016/j.saa.2013.04.032. Epub 2013 Apr 11. doi: 10.1016/j.bbrc.2010.12.084. Epub 2010 Dec 23. doi: 10.1002/chir.22046. Epub 2012 May 10. doi: 10.1002/chem.201303261. Epub 2013 Dec 30. doi: 10.1124/dmd.109.030064. Epub 2009 Nov 12. doi: 10.1107/S0108270111027272. Epub 2011 Aug 5. doi: 10.1002/chem.200902517. doi: 10.1021/ja2054918. Epub 2011 Nov 15. doi: 10.1016/j.talanta.2009.10.011. Epub 2009 Oct 14. doi: 10.1039/c2dt12390h. Epub 2012 Mar 27. doi: 10.1021/acs.joc.5b01491. Epub 2015 Aug 12. Epub 2006 Feb 17.

    合成参考文献


    摘要:Schafer, E. W., Jr., W. A. Bowles Jr., and J. Hurlbut. 1983. The acute oral toxicity and repellency and hazard potential of 998 chemicals to one or more species of wild and domestic birds. Archives of Environmental Contamination and Toxicology 12:355-382.
    摘要:Schafer, E.W., Jr., et al. 1982. Effects of 77 chemicals on reproduction in male and female coturnix quail. Ecotox. Environ. Safety 6:149-156
    摘要:Kleemann A., Kutscher B., Reichert D., Bossart M., Pharmaceutical Substances, Thieme [Online], Stuttgart, (2025).
    摘要:Cunha, J. C.; Dedeiras, B.; Negrão, A. C. R.; Marques, M. M. B., Science of Synthesis: Hypervalent Halogens in Organic Synthesis, (2025) .
    参考文献:10.1021/ac010278p
    摘要:Takeuchi T, Mukawa T, Matsui J, Higashi M, Shimizu KD. Moleculary imprinted polymers with metalloporphyrin-based molecular recognition sites coassembled with methacrylic acid. Anal Chem. 2001 Aug 15;73(16):3869–74. doi: 10.1021/ac010278p.
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