专利号:US-10308588-B2 优先权日:2014-12-15 标 题 :Synthesis of amides and amines from aldehydes or ketones by heterogeneous metal catalysis 发明人:CÓRDOVA ARMANDO; PALO-NIETO CARLOS; AFEWERKI SAMSON 权利人:ORGANOFUEL SWEDEN AB 摘要:A mild and efficient synthesis of primary amines and amides from aldehydes or ketones using a heterogeneous metal catalyst and amine donor is disclosed. The initial heterogeneous metal-catalyzed reaction between the carbonyl and the amine donor components is followed by the addition of a suitable acylating agent component in one-pot, thus providing a catalytic one-pot three-component synthesis of amides. Integration of enzyme catalysis allows for eco-friendly one-pot co-catalytic synthesis of amides from aldehyde and ketone substrates, respectively. The process can be applied to asymmetric synthesis or to the co-catalytic one-pot three-component synthesis of capsaicin and its analogues from vanillin or vanillyl alcohol. A co-catalytic reductive amination/dynamic kinetic resolution (dkr) relay sequence for the asymmetric synthesis of optically active amides from ketones is disclosed. Implementation of a catalytic reductive amination/kinetic resolution (kr) relay sequence produces the corresponding optically active amide product and optical active primary amine product with the opposite stereochemistry from the starting ketones.
专利号:US-11168050-B2 优先权日:2014-03-27 标 题 :Efficient synthesis of amines and amides from alcohols and aldehydes by using cascade catalysis 发明人:CÓRDOVA ARMANDO; BERGLUND PER; ANDERSON MATTIAS; AFEWERKI SAMSON 权利人:XP CHEMISTRIES AB 摘要:The present invention relates generally to an eco-friendly methodology for the conversion of alcohols and aldehydes to amines and amides using an integrated enzyme cascade system with metal- and organocatalysis. More specifically, the present invention relates to synthesis of capsaicinoids starting from vanillin alcohol and using a combination of an enzyme cascade system and catalysts. Furthermore, the method also relates to synthesis of capsaicinoids derivatives starting from vanillin alcohol derivatives and using a combination of an enzyme cascade system and catalysts.
专利号:US-6372461-B1 优先权日:1998-09-18 标题 :Synthesis of vanillin from a carbon source 发明人:FROST JOHN W 权利人:DIRECTORS OPERATING MICHIGAN S 摘要:A bioengineered synthesis scheme for the production of vanillin from a carbon source is provided. The bioconversion methods of the present invention comprise the steps of microbe-catalyzed conversion of a carbon source to vanillic acid followed by enzyme-catalyzed reduction of the vanillic acid to produce vanillin. As shown in the synthesis scheme of FIG. 2, the microbe-catalyzed conversion step of the present invention requires five enzymes which are provided by a recombinant microbe. In a preferred embodiment, the recombinant microbe is Escherichia coli designed to cause dehydration of 3-dehydroshikimic acid and regioselective methylation of the resulting protocatechuic acid. The enzyme-catalyzed reduction step of the present invention comprises the reduction of vanillic acid to vanillin by aryl-aldehyde dehydrogenase.
专利号:EP-1548006-B1 优先权日:2003-12-12 标题 :Synthesis of tetraazapentamethine derivatives, keratin fibers dyeing process which uses such synthesis 发明人:PEREIRA RUI; BURGAUD HERVE 权利人:OREAL 摘要:Producing tetraazapentamethine compounds (I) comprising reacting an azine compound with an oxidizing agent, is new. Producing tetraazapentamethine compounds of formula (I) comprises reacting an azine compound of formula (VI) or (VII) with an oxidizing agent; [Image] [Image] W1a cationic heteroaromatic group of formula (II) or (III); W2a heteroaromatic group of formula (IV) or (V); Z14Z7 or Z1; Z15Z8 or Z2; Z16Z13 or Z0; R25R5 or R1; Z17Z9 or Z3; Z18Z10 or Z4; Z19Z11 or Z5; Z20Z12 or Z6; R26R8 or R3; R27R7 or R4; R28, R29H, 1-6C alkyl or 1-6C alkoxy, but not both H; Z0CR2, N or NR21; Z1O, S or NR9; Z2N or CR10; Z3N or CR11; Z4N or CR12; Z5N or CR13; Z5N or CR13; Z6N or CR14; Z7O, S or NR15; Z8N or CR16; Z9N or CR17; Z10N or CR18; Z11N or CR19; Z12N or CR20; Z13CR6, N or NR22; R2, R6, R10, R16H; 1-4C alkyl substituted with 0-3 of OH, 1-2C alkoxy, 2-4C (poly)hydroxyalkoxy, NH2, 1-2C (di)alkylamino, COOH or SO3H; phenyl substituted with 0-2 of OH, 1-2C alkoxy, 2-4C (poly)hydroxyalkoxy, NH2, 1-2C (di)alkylamino; COOH; sulfonylamino; R1, R4, R5, R7, R9, R15, R21, R221-6C alkyl substituted with 0-3 of OH, 1-2C alkoxy, 2-4C (poly)hydroxyalkoxy, NH2, 1-2C (di)alkylamino, COOH or SO3H; R0, R3, R8, R11-R14, R17-R20H; 1-6C linear or branched hydrocarbyl with 0-3 unsaturations, optionally substituted with 1-3 of OH, 1-2C alkoxy, 2-4C (poly)hydroxyalkoxy, NH2, 1-2C (di)alkylamino, COOH, SO3H, sulfonylamino, 2-4C (poly)hydroxyalkylamino or halo and optionally interrupted by O, N, S or SO2; phenyl optionally substituted with 1-3 of OH, 1-2C alkoxy, 2-4C (poly)hydroxyalkoxy, NH2, 1-2C (di)alkylamino, COOH, SO3H, sulfonylamino, 2-4C (poly)hydroxyalkylamino or halo; pyrazolyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, triazolyl, pyridyl, pyrimidinyl, triazinyl, pyrazinyl or pyridazinyl; X : an anion; R2+R10, R11+R12, R6+R16, R17+R18 can form a 5-6C aromatic ring substituted with 0-2 of OH, NH2, 1-2C (di)alkylamino, 1-2C alkoxy, 2-4C (poly)hydroxyalkylamino. An independent claim is also included for dyeing keratinic fibers by applying (VI) or (VII) onto the wet or dry fibers in the presence of an oxidizing agent. [Image].
专利号:US-7288120-B2 优先权日:2003-12-12 标题 :Synthesis of tetraazapentamethine compounds, and processes for dyeing keratin fibers using this synthesis 发明人:PEREIRA RUI; BURGAUD HERVE 权利人:OREAL 摘要:The present disclosure relates to processes for synthesizing tetraazapentamethine compounds that comprise reacting at least one compound of azine type with at least one oxidizing agent. The disclosure also relates to processes for dyeing keratin fibers, for example human keratin fibers, that comprise using such synthetic processes.
专利号:US-7462470-B2 优先权日:2005-06-17 标 题 :Method for the producing vanillic acid and vanillin from waste residue of rice bran oil by fermentation and biotransformation 发明人:SUN ZHIHAO; ZHENG PU; GUO XINFU; LIN GUANYU; YIN HANGHUA; WANG JUN; BAI YANBING 权利人:ZHEJIANG HANGZHOU XINFU PHARMA 摘要:A method for the production of vanillic acid and vanillin from waste residue (niger) of rice bran oil by microbial fermentation and biotransformation is provided. The method of the present invention comprises the steps of hydrolization of ferulic acid esters in waste residue of rice bran oil to ferulic acid and further conversion into vanillic acid using microbial strain Aspergillus niger CGMCC 0774 screened and preserved by the present inventor, followed by conversion of vanillic acid to produce vanillin using another microbial strain Pycnoporus cinnabarinus CGMCC 1115. The method for the production of vanillin according to the present invention utilizes renewable source from rice processing and alleviates the environmental pollution caused by the chemical synthesis of vanillin.
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