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半导体光催化N氘代烷基化反应机理及底物

来源:心律失常治疗 时间:2024/3/18
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水分解制氢技术日趋成熟,但与传统化石能源制氢技术相比成本尚不具备优势。发展水分解制氢与原位用氢技术,提高输出端产品附加值是解决上述问题的思路之一。近年,苏陈良教授课题组聚焦光(电)催化水分解技术催化调控与应用研究,基于水分解技术提出并实现了以重水为氘源的转移氘化反应,制备了一系列高附加值化学品及医药活性分子:如基于重水裂解技术的碳卤键光催化可控氘代(Nat.Commun.,,9,80;Sci.China.Chem.,)、高晶度碳化氮光催化烯烃、炔烃高选择性氘代(Adv.Sci.,)、电化学窗口指导的电催化惰性碳溴键选择性氘代(Sci.Bull.,j.scib..09.)等。基于上述基础,针对N-烷基类氘代药物可控制备瓶颈问题,以具有合适氧化还原窗口(对比SCE约+1.2V到-1.5V)的高晶度碳化氮为半导体光催化材料,利用光生空穴的强氧化能力氧化醇(或氘标记醇)使生成醛,并与胺缩合转化为亚胺中间体,利用光生电子还原质子提供还原氢[H]/[D](被助催化剂钯所稳定)用于还原亚胺,制得氘标记的N-烷基类化学品和药物。通过调节氘代水和烷基醇的组合实现了在胺类化合物N-位点可控引入-CH3,-CDH2,-CD2H,-CD3,和-13CH3官能团,从而精准合成稳定同位素标记可控的N-烷基药物。

▲图1.a)典型氘标记N-烷基类药物;b)以氘标记甲醇和水为“组合型甲基化试剂”的半导体光催化机理;3)伯胺、仲胺N-甲基化产物氘标记个数精准控制策略。

利用传统方法,目前已有多款N-烷基氘代药物开发出来,部分已经进入临床阶段(图1a)。基于光催化水分解技术,在此提出以氘标记水和甲醇为新型组合型烷基化试剂,从而替代传统昂贵、高毒、剧烈的氘烷基化试剂,并实现氘标记个数精准控制(图1b)。以对甲基苯胺和二苯胺为例,以CH3OH/H2O,CH3OD/D2O,CD3OD/H2O,CD3OD/D2O等方式进行组合时,可实现伯胺二烷基化产物、仲胺烷基化产物氘标记个数精准控制(精准引入-CH3,-CDH2,-CD2H,-CD3),实验结果也验证了图1b提出的催化机制。

图2.半导体光催化N-氘代烷基化反应机理及底物适用性研究。

底物适用性研究表明,该氘代策略适用于系列伯胺、仲胺。醚、氯代物、腈基、酯基等官能团均良好兼容。杂环、长链脂肪胺亦可通过该方法顺利进行氘代烷基化反应。以其他氘代醇替代氘代甲醇时,还可实现N-氘代烷基化反应,如引入N-C2D5。图2数据表明该方法反应温和、产率高、选择性好,氘代率高,官能团适用性良好,具有实用化、规模化制备氘标记N-烷基类药物的潜力。利用该方法随后制备了一系列重要的氘标记N-烷基类药物及生物活性分子,如实现了对雄激素拮抗剂氟他胺,非甾体抗炎药尼美苏利,局部麻醉药丁卡因、非中枢神经兴奋剂阿托莫西汀等商业化药物高效、温和N-氘甲基化反应,产率高达94%,氘代率均高于95%;实现了抗抑郁药丙咪嗪-d3,抗真菌药布替萘芬-d3,阿尔维林-d5系列氘代药物快速制备,产率较高92%,氘代率均大于95%。抗精神药物洛沙平-d3和抗心律失常药物多非利特-d3等克级规模制备进一步验证该方法的实用性(图3)。

图3.后修饰策略制备氘标记N-烷基类药物及其衍生物。

基药物代谢位点氘标记个数控制有利于研究和调节药物代谢、吸收、排泄等特性,利用甲醇和水的组合型烷基化试剂的优势,实现了在布替萘芬,氘代洛沙平和丙咪嗪关键位点不同稳定同位素和不同标记个数精准控制(N-CH3,-CDH2,-CD2H,-CD3,和-13CH3)(图4)。

图4.稳定同位素标记的N-烷基类药物精准合成。

水与有机分子“为原料的人工光合成N-烷基胺类氘代药物的方法,具有条件温和,官能团兼容性好,产率和氘代率高等优点。更为重要的是,通过调控稳定同位素标记的水和醇的调控,实现了N-烷基类药物关键位点不同稳定同位素和不同标记个数的精准控制,为人工光合成高附加值化学品发展提供了新的思路和方法。

CAS号中文名称英文名称

-51-5苯甲醛-D5Benzaldehyde-d5

-63-9溴代异丙烷-D72-Bromopropane-d7

-13-6甲醇-D1Methanol-d1

-57-5溴苯-D5Bromobenzene-d5

-50-9碘甲烷-D3Iodomethane-d3

-19-7二甲胺盐酸盐-D6Dimethyl-d6-aminehydrochloride

-09-72-氨基丙烷-D7Isopropyl-d7-amine

-70-1苯硼酸-D5Phenyl-d5-boronicacid

-92-81,4-二溴丁烷-D81,4-Dibromobutane-d8

-62-2苯酚-D5Phenol-d5

-88-3苯酚-D6Phenol-d6

-63-6溴乙烷-D5Bromoethane-d5

-61-1苯胺-2,3,4,5,6-D5Aniline-d5

-58-1碘乙烷-D5Iodoethane-d5

-56-4对二溴苯-D41,4-Dibromobenzene-d4

-45-8哌嗪-D8二盐酸盐Piperazine-2,2,3,3,5,5,6,6-d8dihydrochloride

-65-7N-甲基哌嗪-2,2,3,3,5,5,6,6-D8N-Methylpiperazine-d8

-87-8二乙胺盐酸盐-D10Dityhyl-d10-animehydrochloride

-47-24-羟基苯甲酸-D44-Hydroxybenzoic-2,3,5,6-d4acid

-11-5叔丁醇-D92-Methyl-2-propanol-d9

-33-72-碘丙烷-D72-Iodopropane-d7

-56-12-(2-羟基乙氧基)乙醇-D82-(2-Hydroxyethoxy)ethanol-d8

-31-6正丙醇-D7N-Propanol-d7

-58-21,2-苯二酚-3,4,5,6-D41,2-Benzene-3,4,5,6-d4-diol

-02-3苯甲酸-D5Benzoicacid-2,3,4,5,6-d5

-64-84-溴苯甲醛-D44-Bromobenzaldehyde-d4

-14-51-甲基-4-哌啶酮-2,2,6,6-D41-Methyl-4-piperidone-2,2,6,6-d4

-81-9苄胺-D5Benzyl-2,3,4,5,6-d5-amine

-98-1庚酸-D5Heptanoicacid-d5

-84-4三乙氧基硅烷-D1Triethoxysilane-d

-37-8三(2-乙基己基)磷酸酯-D51Tris(2-ethylhexyl)phosphate-d51

-17-6丁香酚-D3Eugenol-d3

-64-0叔丁胺-D9-盐酸盐tert-Butylamine-d9hydrochloride

-42-6丁二酸-2,2,3,3-D4Succinicacid-d4

-85-13-(苯基-2,3,4,5,6-D5)-9H-咔唑9H-Carbazole,3-(phenyl-2,3,4,5,6-d5)-

-93-8苯甲醛-D6Benzaldehyde-d6

-91-5甲基乙酸-2,2-D2Propionic-2,2-d2acid

-33-4对氯苯胺-D44-Chloroaniline-d4

-13-33-甲基吡啶-D73-Methylpyridine-d7

-39-7噻吩-D4Thiophene-d4

-69-11,2-二氯苯-D41,2-Dichlorobenzene-D4

-72-61,2,4-三氯苯-D31,2,4-Trichlorobenzene-d3

-51-4乙二醇-D4Ethylene-d4glycol

-74-5异丁酸-D72-Methylpropionic-d7acid

-79-21-Boc-4-(4-氨基苯基)哌嗪-D81-Boc-4-(4-aminophenyl)piperazine-d8

-63-11,2-二溴乙烷-D41,2-Dibromoethane-d4

-14-51-碘丙烷-D21-Iodopropane-d2

-64-7苯乙酮-D5Acetophenone-d5

-59-4苯甲醛-DBenzaldehyde-d1

-52-84-羟基苯甲醛-2,3,5,6-D44-Hydroxybenzaldehyde-d4

-81-3氨基乙烷-D5盐酸盐Ethyl-d5-aminehydrochloride

-96-4苯丙酮-D10Propiophenone-d10

-08-8异丁酸-D6Isobutyric-d6acid

-23-1琥珀酸二甲酯-2,2,3,3-D4Dimethylsuccinate-d4

-12-72-(苯基-2,3,4,5,6-D5)-9H-咔唑9H-Carbazole,2-(phenyl-2,3,4,5,6-d5)-

-98-4甲醇-13C,D4Methanol-13C,d4

-51-3马来酸酐-D2Maleic-d2anhydride

-02-3吗啉-D8Morpholine-2,2,3,3,5,5,6,6-d8

-19-8对硝基溴苯-D41-Bromo-4-nitrobenzene-d4

-01-84-氨基苯甲酸-D44-Aminobenzoicacid-d4

-93-0溴苄-D7Benzyl-d7bromide

-22-0甲胺-15N盐酸盐Methylamine-15Nhydrochloride

-25-6叔丁醇-D2-Methyl-2-propan-d

-63-0苯甲醚-D3Methoxy-d3-benzene

-44-02-羟基异丁酸甲酯-D6Methyl2-hydroxy-2-methyl-d3-propionate-3,3,3-d3

-21-11,3-丙二醇-D41,3-Propanediol-d4

-93-22-乙酰基丁内酯-3,3,4,4-D42-Acetylbutyrolactone-3,3,4,4-d4

-59-2异丙胺-D6Isopropyl-d6-amine

-88-3甲基乙酸-3,3,3-D3Propionic-3,3,3-d3acid

/8/5叔丁胺-D9Tert-butyl-d9-amine

-86-3氯化胆碱-三甲基-D9Choline-d9chloride

-71-0丙三醇-D5Glycerol-d5

-41-4三氟甲磺酸-DTrifluoromethanesulfonicacid-d

-23-6对硝基氯苯-D44-Chloronitrobenzene-d4

-22-8甲胺盐酸盐-D3Methyl-d3-aminehydrochloride

-94-6二甲胺-15N盐酸盐Dimethylamine-15-nhydrochloride

-65-1γ-丁内酯-D6γ-Butyrolactone-d6

-24-2对溴苯甲酸-D44-Bromobenzoic-d4acid

-56-9丙二酸-D4Malonicacid-d4

-24-84-氯代甲苯-2,3,5,6-D44-Chlorotoluene-2,3,5,6-d4

-70-7硫酸肼-15N2Hydrazinesulfate-15N2

-71-5甲酸-DFormicacid-d

-20-7叔丁基氯-D9T-butylchloride-d9

-81-22,6-二甲基苯胺-D62,6-Dimethylaniline-d6

-42-3甲酸-D2Formicacid-d2

-93-9乙醇-D1Ethanol-d

-36-91-溴丁烷-D91-Bromobutane-d9

-30-8丙酮酸-1-13CPyruvicacid-1-13C

-09-62-氯-4,6-二(苯基-2,3,4,5,6-D5)-1,3,5-三嗪1,3,5-Triazine,2-chloro-4,6-di(phenyl-2,3,4,5,6-d5)-

/4-氨基-2-氟苯酚-D34-Amino-2-fluorophen-3,5,6-d3-ol

/N-Boc-哌嗪-D4N-Boc-piperazine-d4

/3-甲基-D3-苄溴3-Methyl-d3-benzylbromide

-28-92,6-二氯-4-氨基苯酚-D24-Amino-2,6-dichlorophenol-d2

/2,3-二甲基溴苯-D62,3-Dimethylbromobenzene-d6

-59-12-氯-4-苯基-6-(苯基-2,3,4,5,6-D5)-1,3,5-三嗪1,3,5-Triazine,2-chloro-4-phenyl-6-(phenyl-2,3,4,5,6-d5)-

-62-52,4-二氯-6-(苯基-2,3,4,5,6-D5)-1,3,5-三嗪1,3,5-Triazine,2,4-dichloro-6-(phenyl-2,3,4,5,6-d5)-

-95-09-(苯基-2,3,4,5,6-D5)-3-(4,4,5,5-四甲基-1,3,2-二氧杂硼烷-2-基)-9H-咔唑9H-Carbazole,9-(phenyl-2,3,4,5,6-d5)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-

/N-甲基-(S)-2-吡咯烷甲醇-D5N-Methyl-(s)-2-pyrrolidinemethanol-d5

-91-63-溴-9-(苯基-2,3,4,5,6-D5)-9H-咔唑9H-Carbazole,3-bromo-9-(phenyl-2,3,4,5,6-d5)-

/苯乙炔-D5Phenylacetylene-d5

/4,5-二甲基-1,2-苯二胺-D64,5-Dimethyl-1,2-phenylenediamine-d6

-49-5溴乙酸乙酯-13C2EthylBromoacetate-1,2-13C2

-37-0硝基苯-13C6Nitrobenzene-13C6

-37-2烯丙基溴-D5Allyl-d5bromide

/(±)-1-氨基-2-丙醇-1,1,2,3,3,3-D6(±)-1-Amino-2-propanol-1,1,2,3,3,3-d6

-55-41,2-丙二醇-D81,2-Propanediol-d8

-86-0N-Boc-哌嗪-D8Piperazine-d8-n-t-boc

-43-0甲基碘-D2Iodomethane-d2

-96-1碘甲烷-D1Iodomethane-d1

-85-4蜡酸-D4Hexacosanoic--d4acid

-61-2焦油酸-D4Tetracosanoic-9,9,10,10-d4acid

-60-0硝基苯-D5Nitrobenzene-d5

-35-3邻溴氟苯-D42-Bromofluorobenzene-d4

-55-4氯苯-D5Chlorobenzene-d5

-05-5苄氯-D7Benzyl-d7chloride

-35-9甲胺-N,N-D2Methylamine-N,N-d2

-55-5甲基-D3-胺Methyl-d3-amine

-79-1吡咯烷-2,2,3,3,4,4,5,5-D8Pyrrolidine-2,2,3,3,4,4,5,5-d8

-69-9己酸-D3Hexanoic-6,6,6-d3acid

-04-3庚酸-D3Heptanoic-7,7,7-d3acid

-64-3UN9-溴蒽-D99-Bromoanthracene-d9

-13-2UN2-溴萘-D72-Bromonaphthalene-d7

-44-5对溴甲苯-D34-Bromotoluene-d3

-53-84-羰基-Tempo-D-Piperidinyl-3,3,5,5-d4-oxy,2,2,6,6-tetra(methyl-d3)-4-oxo-

-76-42-溴丙烷-1,1,1,3,3,3-D62-Bromo-1,1,1,3,3,3-hexadeuteriopropane

-71-12-溴吡啶-D42-Bromopyridine-d4

-99-3戊二酸-D6Pentanedioic-d6acid

-51-9二苯胺-D10Diphenylamine-d10

-42-5哌嗪-D8Piperazine-d8

-66-3苯酚-DPhenol-d

-76-0异丙醇-D82-Propanol-d8

-51-9异丙醇-D2-Propanol-d

-55-44-辛基-D17-苯酚4-N-Octyl-d17-phenol

-41-2双酚A-D4Bisphenol-a-3,3,5,5-d4

-90-2哌啶-D11Piperidine-d11

-54-14-甲氧基-D3-苯甲酸4-Methoxy-d3-benzoicacid

-83-84-溴联苯醚-D54-Bromophenylphenyl-d5ether

19-90-6乙酰氯-D3Acetylchloride-d3

-65-12-甲基-1,4-萘二酚-D82-Methyl-1,4-naphthalenediol-d8

-63-73-甲基-喹喔啉-2-羧酸-D43-Methyl-quinoxaline-2-carboxylicacid-d4

-02--溴蒽-D9Anthracene-1,2,3,4,5,6,7,8,9-d9,10-bromo-

-01-2氘代3-氯-1,2-丙二醇3-Chloro-1,2-propane-d5-diol

-05-42-氯-1,3-丙二醇-D52-Chloro-1,3-propanediol-d5

-20-6氘代-1,3-二氯-2-丙醇1,3-Dichloro-iso-propyl-d5alcohol

-57-7三甲基-D9-氯硅烷Trimethyl-d9-chlorosilane

-42-01-溴丁烷-4,4,4-D31-Bromobutane-4,4,4-d3

-81-44-氟苯胺-2,3,5,6-D44-Fluoroaniline-2,3,5,6-d4

-24-59H-咔唑-1,2,3,4,5,6,7,8-D89H-Carbazole-1,2,3,4,5,6,7,8-d8

-36-9二甲基-D6-胺Dimethyl-d6-amine

-19-5乙烯-D4-二胺Ethylene-d4-diamine

-67-6邻三联苯-D14O-terphenyl-d14

-93-1对甲苯磺酰甲酯-D34-Methylbenzenesulfonate-d3

-90-84-氟苯硼酸-D44-fluoro(phenyl-d4)-boronicacid

-53-1原甲酸三乙酯-D1Triethylorthoformate-d1

-10-0异丙胺盐酸盐-D7Isopropyl-d7-aminehydrochloride

-84-8正己醇-D13N-hexyl-d13alcohol

-49-5环己酮-D10Cyclohexanone-d10

-46-61-溴-3-氯丙烷-D61-Bromo-3-chloropropane-d6

-86-1乙二醇-D6Ethyleneglycol-d6

-43-73-溴-1-丙醇-D63-Bromopropanol-d6

-08-12-氨基(乙醇-1,1,2,2-D4)Ethanol-1,1,2,2-d4-amine

-54-2N-亚硝基甲乙胺-D3N-nitrosoethylmethyl-d3-amine

-09-1N-亚硝基吡咯烷-D8N-nitrosopyrrolidine-d8

-21-2N-亚硝基哌啶-D10N-nitrosopiperidine-d10

-03-7邻苯二甲酸酯-D4Monoethylphthalate-d4

-82-1丙烯酸-D4Acrylicacid-d4

-52-3乙酸-D4Aceticacid-d4

-66-2二乙基-D10-胺Diethyl-d10-amine

-96-1异丙醇-D7Isopropanol-d7

-57-02-氨基吡啶-D62-Aminopyridine-d6

-26-5甲苯-D8Toluene-d8

-32-9邻苯二甲酸酐-D4Phthalicanhydride-d4

-38-3丁醇-D1-Butanol-d

-55-82-溴乙醇-1,1,2,2-D42-bromoethanol-1,1,2,2-d4

-22-5溴化苄-D5Benzyl-d5bromide

-23-4苯胺-D7Aniline-d7

-24-9氨基乙烷-D5Ethyl-d5-amine

-37-2N-乙基马来酰亚胺-D5N-Ethyl-d5-maleimide

-20-3吲哚-D7Indole-d7

-78-5吲哚-2,4,5,6,7-D5-3-乙酸Indole-2,4,5,6,7-d5-3-aceticacid

-56-5盐酸吗啡啉-D8Morpholine-d8hydrochloride

-12-04,4-二甲基-环己酮-2,2,6,6,-D44,4-dimethyl-cyclohexanone-2,2,6,6,-d4

-92-6丙酸-D5Propionicacid-d5

-32-3正二十四烷-D50N-Tetracosane-d50

-58-2邻苯二酚-D4Catechol-d4

-41-94-甲基儿茶酚-D34-Methyl-d3-catechol

-29-22-丙醇-1,1,1,3,3,3-D62-Propanol-1,1,1,3,3,3-d6

-54-6环氧氯丙烷-D5Epichlorohydrin-d5

-03-7环己酮-2,2,6,6-D4Cyclohexanone-2,2,6,6-d4

-51-24-羟基苯甲酸甲酯-2,3,5,6-D4Methyl4-hydroxybenzoate-2,3,5,6-d4

-22-22-甲基-2-丙醇-D10Tert-butanol-d10

-83-8叔丁基溴-D92-bromo-2-methylpropane-d9

-51-0对三联苯-D-terphenyl-d14

-82-11,4-二氯苯-D41,4-dichlorobenzene-d4

-00-8对甲酚-D34-Methylphenol-d3

-52-8对甲酚-D74-Methylphenol-d7

-13-7对氯苯磺酰氯-D44-Chlorobenzenesulfonylchloride-d4

-49-4对甲苯磺酰氯-D74-Methylbenzenesulfonylchloride-d7

-17-9丙三醇-D8Glycerol-d8

-25-81,4-丁烷二醇-2,2,3,3-D41,4-Butanediol-2,2,3,3-d4

-86-51-萘甲醇-D71-Naphthalenemethanol-d7

-67-84-溴甲苯-D74-Bromotoluene-d7

-66-73-甲基苄醇-D33-Methyl-d3-benzylalcohol

-34-29-芴酮-D89-Fluorenone-d8

-49-1十六烷酸-D4Hexadecanoic-7,7,8,8-d4acid

-63-11,4-二溴丁烷-2,2,3,3-D41,4-Dibromobutane-2,2,3,3-d4

-10-9苄醇-2,3,4,5,6-D5Benzyl-2,3,4,5,6-d5alcohol

-88-94-氨基苯酚-D74-Aminophenol-d7

-83-7正丁酸-D7Butyricacid-d7

-85-2对溴甲苯-D44-Bromotoluene-2,3,5,6-d4

-28-92,6-二氯-4-氨基苯酚-D24-Amino-2,6-dichlorophen-3,5-d2-ol

-17-0水杨酸-D42-Hydroxybenzoic-3,4,5,6-d4acid

-25-24-氟苯甲酸-D44-Fluorobenzoic-d4acid

-69-0荧蒽-D10Fluoranthene-d10

-71-7苯并(A)芘-D12Benzo[a]pyrene-d12

-43-7十二烷酸-D23Dodecanoic-d23acid

-51-4十八酸-D35Octadecanoic-d35acid

-26-01-萘基-2,3,4,5,6,7,8-D7-硼酸Boronicacid,b-(1-naphthalenyl-2,3,4,5,6,7,8-d7)-

-62-94-壬基酚-2,3,5,6-D44-Nonylphenol-2,3,5,6-d4

-40-94-溴-1,1-联苯-2,3,4,5,6-D54-Bromo-1,1-biphenyl-2,3,4,5,6-d5

-00-11,1-联苯-2,2,3,3,4,5,5,6,6-D91,1-Biphenyl-2,2,3,3,4,5,5,6,6-d9

-27-14-溴-1,1-联苯-2,3,5,6-D4(9Ci)1,1-Biphenyl-2,3,5,6-d4,4-bromo-(9ci)

-39-63-溴-1,1-联苯-2,3,4,5,6-D5(9Ci)1,1-Biphenyl-2,3,4,5,6-d5,3-bromo-(9ci)

-97-1[1,1-联苯-2,3,3,4,4,5,5,6,6-D9]-2-胺(9Ci)[1,1-Biphenyl-2,3,3,4,4,5,5,6,6-d9]-2-amine(9ci)

-38-52-溴-1,1-联苯-2,3,4,5,6-D51,1-Biphenyl-2,3,4,5,6-d5,2-bromo-

-95-72-氟-1,1-联苯-2,3,4,5,6-D51,1-Biphenyl-2,3,4,5,6-d5,2-fluoro-(9ci)

-93-7[1,1-联苯-2,2,3,4,4,5,5,6,6-D9]-3-胺[1,1-Biphenyl-2,2,3,4,4,5,5,6,6-d9]-3-amine

-54-92-萘酚-D72-Naphthol-d7

-84-91-萘酚-D71-Naphthol-d7

-20-03,4-二羟基苯甲醛-D33,4-Dihydroxybenzaldehyde-d3

-94-03,3,5,5-吗啉-D4Morpholine-3,3,5,5-d4

-08-94-氨基苯甲酸乙酯-D4Benzocaine-d4

-66-54-硝基苯甲酸-D44-Nitrobenzoic-d4acid

-07-23,4-二(甲氧基-D3)苯乙胺3,4-di(Methoxy-d3)benzeneethanamine

-55-4异烟酸-D4Isonicotinic-d4acid

-44-0氘代己酸-D11Hexanoic-d11acid

-94-1己基溴-D-Bromohexane-d13

-52-22-(甲基-D3)溴苯2-(Methyl-d3)bromobenzene

-04-6二苯并呋喃-D8Dibenzofuran-d8

-27-51H-吲哚-2,3,4,5,6,7-D61H-Indole-2,3,4,5,6,7-d6

-13-62-甲基苯胺-D32-(Methyl-d3)aniline

-26-9邻苯二甲酸-D4Phthalicacid-d4

-36-6丁醛-D8Butanal-d8

-13-8乙醛-DAcetaldehyde-1-d1

-15-6乙醛-2,2,2-D3Acetaldehyde-d3

-60-1金刚烷-D16Adamantane-d16

-28-42-氯苯甲酸-D42-Chlorobenzoicacid-d4

-54-41,2-二甲基-D6-苯O-xylene-d6

-13-2犬尿喹啉酸-D5Kynurenicacid-d5

-93-12-氨基异丁酸-D62-Methylalanine-d6

265-93-01,2-苯二胺-D41,2-Benzene-d4-diamine

-52-92-氘代吲哚Indole-2-d

-36-63-氘代吲哚Indole-3-d

-95-74-壬基酚-2,3,5,6-D4,Od4-Nonylphenol-2,3,5,6-d4,od

-03-71-萘酚-D81-Naphthol-d8

75-50-3UN三甲胺-D9Trimethylamine-d9

-25-0对甲基苯胺-D34-(Methyl-d3)aniline

-42-1噻吩-D2Thiophene-2,5-d2

-27-32-溴-5-甲基苯-1,3-D2Benzene-1,3-d2-2-bromo-5-methyl

-50-14-溴苯酚-2,6-D2Phen-2,6-d2-ol,4-bromo

-35-3脲-13C,15N2Urea-13c,15n2

-87-24-(2-羟乙基)-1-哌嗪乙磺酸-D18N-2-hydroxyethylpiperazine-n′-ethanesulfonicacid-d18

-20-7肌酸酐-(甲基-D3)Creatinine-d3

-66-5环己烷-1,2-二胺-D,2-Cyclohexane-d10-diamine

-14-93-溴吡啶-D43-Bromopyridine-d4

-18-1甲苯-D3Toluene-d3

-99-2甲苯-2,3,4,5,6-D5Toluene-d5

-54-44-(乙酰基-D3)-溴苯4-(Acetyl-d3)-bromobenzene

/3,5,6-三氘代-4-氨基-2-氟苯酚4-Amino-2-fluorophen-3,5,6-d3-ol

-27-44-氟苯甲醛-2,3,5,6-D44-Fluorobenzaldehyde-2,3,5,6-d4

-30-4十六烷酸-D31Palmiticacid-d31

-62-7苯乙烯-D8Styrene-d8

-36-6辛基溴-D-Bromooctane-d17

-57-2甲基丙二酸二乙酯-D3Diethylmethyl-d3-malonate

-65-42,3-二甲基吡啶-D92,3-Dimethylpyridine-d9

-81-84-羟基苯甲酸苯甲酯-D4Benzyl4-hydroxybenzoate-2,3,5,6-d4

-65-0双氯芬酸D4Diclofenac-d4

-88-7甲酰胺-1-DFormamide-1-d1

-75-1苯甲酮-D10Benzophenone-d10

/1/91H-咪唑-D4Imidazole-d4

-30-5烯丙醇-D5Allyl-d5alcohol

-90-41-甲基-D3环丙醇1-Methyl-d3-cyclopropanol

116-67-91,9-壬二酸-D,9-Nonanedioic-d14acid

-16-3乙酰水杨酸-D42-Acetoxybenzoic-3,4,5,6-d4acid

-74-3己醛-D12Hexanal-d12

1245-80-64-氨基环己醇-D-Aminocyclohexanol-d10

-26-7异丙醇-2-D12-Propan-2-d-ol

-89-5环戊酮-2,2,5,5-D4Yclopentanone-2,2,5,5-d4

84-82-3环丙烷羧酸-D4Cyclopropane-2,2,3,3-d4-carboxylicacid

-48-97-溴萘-D7Naphthalene-1,2,3,4,5,6,8-d7,7-bromo

-61-6邻二甲苯-D10O-xylene-d10

-95-0环丙胺-D5Cyclopropylamine-d5

-49-3乙酸酐-D6Aceticanhydride-d6

-15-1邻苯二甲醚-D41,2-Dimethoxybenzene-3,4,5,6-d4

-99-65-氯-2-氨基吡啶-3,4,6-D35-Chloro-2-pyridinamine-3,4,6-d3

-23-3对甲基苯胺-D9P-Toluidine-d9

-44-94-溴苯酚-2,3,5,6-D44-Bromophenol-2,3,5,6-d4

7793-94-05-甲基吗啉-3-氨基-2-恶唑烷基酮-D53-amino-5-(4-morpholinylmethyl-d2)-2-oxazolidinone-4,4,5-d3

-57-43,4-二氨基甲苯-D63,4-Diaminotoluene-d6

-09-55-溴-6-硝基苯-1,2,3,4-D41-Bromo-2-nitrobenze-d4

-78-3邻苯二胺-D81,2-Phenylenediamine-d8

-29-9苯并咪唑-4,5,6,7-D4Benzimidazole-4,5,6,7-d4

-60-42-溴-4-甲基吡啶-D62-Bromo-4-methylpyridine-d6

-24-12-溴-4-(叔丁基-D9)-吡啶2-Bromo-4-(tert-butyl-d9)-pyridine

-03-92-溴-5-(甲基-D3)-吡啶2-Bromo-5-(methyl-d3)-pyridine

-50-8均四甲苯-D,2,4,5-Tetramethylbenzene-d14

-73-13,5-二甲氧基苯甲醛-D63,5-Dimethoxybenzaldehyde-d6

-61-82-羟基萘-D82-Naphthol-d8

-62-6UN丙酸酐-D2Propanoic-2,2-d2anhydride

1-29-0异丙苯-D62-Phenylpropane-1,1,1,3,3,3-d6

-69-5异丁醇-D62-Methyl-d3-propyl-3,3,3-d3alcohol

-07-3三甲基乙酸-D9Trimethyl-d9-aceticacid

-62-0丁二酸二乙酯-2,2,3,3-D4Diethylsuccinate-2,2,3,3-d4

-53-4对乙酰氨基酚-D7N-(4-hydroxyphenyl-2,3,5,6-d4)acetamide-2,2,2-d3

-77-71,3-丙二醇-D61,3-Propane-d6-diol

-07-9苯乙酸-2,2-D2Phenylacetic-2,2-d2acid

-12-6水杨酸甲酯-D4Methyl2-hydroxybenzoate-d4

-62-75-溴戊酸-3,3,4,4-D45-Bromopentanoic-3,3,4,4-d4acid

-91-83,3-二氯联苯胺D63,3-Dichlorobenzidine-d6

-85-6四咪唑-D5盐酸盐Tetramisole-d5hydrochloride

22-33-3溴苯-4-D1Benzene-d,4-bromo-

22-34-4氯苯-4-D11-Chlorobenzene-4-d

-28-11,4-二羟甲基苯-D41,4-di(Hydroxymethyl)benzene-d4

-69-71,2-环氧丙烷-D61,2-Propylene-d6oxide

-25-8糠醇-D2Furfurylalcohol-d2

-47-9软脂酸-D4Palmiticacid-d4

-44-1溴代环戊烷-D9Cyclopentyl-d9bromide

-08-5N-(甲基-D3)-哌嗪N-(Methyl-d3)-piperazine

-83-54-甲基-3-戊烯-2-酮-D-Methyl-3-penten-2-one-d10

-49-5丙二酸二乙酯-D2Diethylmalonate-d2

-27-4苯乙酸-D7Phenylacetic-d7acid

-63-7苯乙醇-D52-Phenyl-d5-ethanol

-37-2溴丙烯-D5Allyl-d5bromide

-66-44-碘甲苯-D74-Iodotoluene-d7

4695-53-41-Boc-4-哌嗪-2,2,6,6-D41-Boc-4-Piperidone-2,2,6,6-d4

-38-9丙酮酸乙酯-D3Ethylpyruvate-3,3,3-d3

-90-6琥珀酸-D6Succinicacid-d6

-68-52-咪唑烷酮-D4Ethyleneurea-d4

-79-1哌嗪-D10Piperidine-d10

-54-0环丁酮-2,2,4,4-D4Cyclobutanone-2,2,4,4-d4

-80-5溴代异丙烷-2-D12-Bromopropane-2-d1

-77-02,4-二硝基酚D32,4-Dinitrophenol-d3

-04-54-甲氧基苯甲醛-D34-Methoxy-d3-benzaldehyde

-08-34-甲基苯胺-D74-(Methyl-d3)benzen-2,3,5,6-d4-amine

-21-42-(甲基-D3)-苯硼酸2-(Methyl-d3)-phenylboronicacid

-47-63-苯基-2-丙烯酸-D73-Phenyl-2-propenoicacid-d7

-55-64-甲氧基苯胺-D44-Methoxyaniline-d4

-50-6戊酸-D9Pentanoic-d9acid

-54-3N-亚硝基二乙胺-D10N-Nitrosodiethylamine-d10

-41-1二异丙胺-D14Di-iso-Propyl-d14-amine

-32-9二丁胺-D18Di-n-Butyl-d18-amine

-51-5乙基-2,2-D2甲酸-DPropionic-2,2-d2acid

-87-6双酚A-D16Bisphenola-d16

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