CAS: 85-63-2; (R)-Laudanosine

英文名称(R)-Laudanosine
中文名称阿曲库铵杂质N
CAS编号85-63-2
MFCD编号:MFCD21496425
FDA UNII编号:EO6NL5AZ5Z
分子式:C21H27NO4
分子量:357.44
产品CID: 1853774
产品分类分析化学 → 标准品 → 药典标准品和杂质标准品

相似结构搜索
InChIKey: KGPAYJZAMGEDIQ-QGZVFWFLSA-N
1S/C21H27NO4/c1-22-9-8-15-12-20(25-4)21(26-5)13-16(15)17(22)10-14-6-7-18(23-2)19(11-14)24-3/h6-7,11-13,17H,8-10H2,1-5H3/t17-/m1/s1…
计算化学: 氢键受体数5.0氢键供体数0.0可旋转键数6.0

物理性质

熔点87-89 ºC
密度1.111±0.06 g/cm3 (20 ºC 760 Torr),
PSA:40.16
LogP:3.7
溶解性Chloroform (Slightly), DMSO (Slightly, Sonicated), Ethanol (Slightly), Methanol
外观形态白色至类白色固体

上下游产品

laudanosine N-[((1R,2S,5R)-8-phenylmenthoxy)carbonyl]-1-(4,5-dimethoxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline -2-formyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline(Z)-1-(3,4-Dimethoxyphenyl)methylene-2-formyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 2-[(4S)-4,5-dihydro-4-(1-methylethyl)-2-oxazolyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (-)-(R)-glaucine 2'-(β-N-Methyl-N-ethoxycarbonyl)aminoethyl-3,3',4,4'-tetramethoxystilben

合成工艺路线路线简述

合成目标产物 (R)-1-(3,4-Dimethoxybenzyl)-6,7-Dimethoxy-2-Methyl-1,2,3,4-Tetrahydroisoquinoline 主要起始原料 Formaldehyde And (R)-(+)-Tetrahydropapaverine
2850222-58-9 = 85-63-2
反应条件:1.1 Reagents: Diisobutylaluminum Hydride Solvents: Toluene,Tetrahydrofuran; 0 °C; 0 °C -> Rt; 1 H,Rt1.2 Reagents: Potassium Sodium Tartrate Solvents: Water; 30 Min,Rt
标题:A Catalytic Asymmetric Pictet-Spengler Platform As A Biomimetic Diversification Strategy Toward Naturally Occurring Alkaloids
作者:Scharf,Manuel J.; Et Al
参考文献:Journal Of The American Chemical Society 日期:2022 卷标:144(34) 页码:15451-15456]

116071-85-3 + 2258-42-6 = 85-63-2
反应条件:1.1 -1.2 Reagents: Lithium Aluminum Hydride
标题:Synthesis Of R-Laudanosine And 9-R-O-Methylflavinantine By Asymmetric Alkylation
作者:Gawley,Robert E.; Et Al
参考文献:Tetrahedron Letters 日期:1988 卷标:29(3) 页码:301-2]

54417-53-7 = 85-63-2
反应条件:1.1 Reagents: Sodium Acetate,Zinc Chloride,Sodium Cyanoborohydride Solvents: Methanol; 24 H,Rt
标题:Organocatalytic Enantioselective Pictet-Spengler Approach To Biologically Relevant 1-Benzyl-1,2,3,4-Tetrahydroisoquinoline Alkaloids
作者:Ruiz-Olalla,Andrea; Et Al
参考文献:Journal Of Organic Chemistry 日期:2015 卷标:80(10) 页码:5125-5132]

116071-85-3 + 119110-16-6 = 85-63-2 [标题:Reaction Conditions
标题:Product Subclass 21: α-Lithioamines
作者:Gawley,Robert E.; Et Al
参考文献:Science Of Synthesis 日期:2006 卷标:8 页码:677-757]

7306-46-9 + 102922-34-9 = 85-63-2
反应条件:1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran2.1 -2.2 Reagents: Lithium Aluminum Hydride
标题:Synthesis Of R-Laudanosine And 9-R-O-Methylflavinantine By Asymmetric Alkylation
作者:Gawley,Robert E.; Et Al
参考文献:Tetrahedron Letters 日期:1988 卷标:29(3) 页码:301-2]

136114-04-0 + 136114-02-8 = 85-63-2
反应条件:1.1 Reagents: Phosphorus Oxychloride Solvents: Dichloromethane2.1 Reagents: Lithium Aluminum Hydride Solvents: Tetrahydrofuran
标题:Asymmetric Pictet-Spengler Synthesis Of Tetrahydroisoquinolines. An Enantioselective Synthesis Of (-)-Laudanosine
作者:Comins,Daniel L.; Et Al
参考文献:Tetrahedron Letters 日期:1991 卷标:32(26) 页码:2995-6]

= 85-63-2
反应条件:1.1 Reagents: Lithium Aluminum Hydride Solvents: Tetrahydrofuran; Cooled; 48 H,Rt1.2 Reagents: Sodium Hydroxide Solvents: Water; 0 °C2.1 Reagents: Diisopropylamine,Butyllithium Catalysts: (3Ar,3′ar,4S,4′s,7R,7′r,7As,7′as)-2,2′-(1-Methylethylidene)Bis[3A,4,5,6,7,7A-Hex... Solvents: Toluene,Hexane; 5 H,0 °C2.2 Reagents: Ammonium Chloride Solvents: Water2.3 Reagents: Potassium Carbonate Solvents: Water; Basified
标题:Asymmetric Total Synthesis Of (-)-Javaberine A And (-)-Epi-Javaberine A Based On Catalytic Intramolecular Hydroamination Of N-Methyl-2-(2-Styrylaryl)Ethylamine
作者:Uenishi,Saho; Et Al
参考文献:Tetrahedron 日期:2021 卷标:90]

= 85-63-2
反应条件:1.1 Reagents: Potassium Carbonate Solvents: Acetonitrile; 18 H,80 °C1.2 Reagents: Hydrochloric Acid Solvents: Dichloromethane; 24 H,Rt2.1 Reagents: Sodium Acetate,Zinc Chloride,Sodium Cyanoborohydride Solvents: Methanol; 24 H,Rt
标题:Organocatalytic Enantioselective Pictet-Spengler Approach To Biologically Relevant 1-Benzyl-1,2,3,4-Tetrahydroisoquinoline Alkaloids
作者:Ruiz-Olalla,Andrea; Et Al
参考文献:Journal Of Organic Chemistry 日期:2015 卷标:80(10) 页码:5125-5132]

= 85-63-2
反应条件:1.1 Reagents: Diisopropylamine,Butyllithium Catalysts: (3Ar,3′ar,4S,4′s,7R,7′r,7As,7′as)-2,2′-(1-Methylethylidene)Bis[3A,4,5,6,7,7A-Hex... Solvents: Toluene,Hexane; 5 H,0 °C1.2 Reagents: Ammonium Chloride Solvents: Water1.3 Reagents: Potassium Carbonate Solvents: Water; Basified
标题:Asymmetric Total Synthesis Of (-)-Javaberine A And (-)-Epi-Javaberine A Based On Catalytic Intramolecular Hydroamination Of N-Methyl-2-(2-Styrylaryl)Ethylamine
作者:Uenishi,Saho; Et Al
参考文献:Tetrahedron 日期:2021 卷标:90]

50896-90-7 + 4525-33-1 = 85-63-2
反应条件:1.1 Solvents: Dichloromethane1.2 Reagents: Lithium Aluminum Hydride Solvents: Diethyl Ether1.3 Reagents: Sodium Hydroxide Solvents: Water
标题:A Novel Straightforward Synthesis Of Enantiopure Tetrahydroisoquinoline Alkaloids
作者:Pedrosa,Rafael; Et Al
参考文献:Journal Of Organic Chemistry 日期:2001 卷标:66(1) 页码:243-250]

136114-05-1 = 85-63-2
反应条件:1.1 Reagents: Lithium Aluminum Hydride Solvents: Tetrahydrofuran
标题:Asymmetric Pictet-Spengler Synthesis Of Tetrahydroisoquinolines. An Enantioselective Synthesis Of (-)-Laudanosine
作者:Comins,Daniel L.; Et Al
参考文献:Tetrahedron Letters 日期:1991 卷标:32(26) 页码:2995-6]

= 85-63-2
反应条件:1.1 Reagents: Lithium Aluminum Hydride Solvents: Tetrahydrofuran
标题:Asymmetric Pictet-Spengler Synthesis Of Tetrahydroisoquinolines. An Enantioselective Synthesis Of (-)-Laudanosine
作者:Comins,Daniel L.; Et Al
参考文献:Tetrahedron Letters 日期:1991 卷标:32(26) 页码:2995-6]

50896-90-7 + 2258-42-6 = 85-63-2
反应条件:1.1 -1.2 Reagents: Lithium Aluminum Hydride
标题:Synthesis Of R-Laudanosine And 9-R-O-Methylflavinantine By Asymmetric Alkylation
作者:Gawley,Robert E.; Et Al
参考文献:Tetrahedron Letters 日期:1988 卷标:29(3) 页码:301-2]

104713-02-2 = 85-63-2
反应条件:1.1 Reagents: Lithium Aluminum Hydride
标题:Asymmetric Synthesis Of Isoquinoline Alkaloids By Homogeneous Catalysis
作者:Noyori,Ryoji; Et Al
参考文献:Journal Of The American Chemical Society 日期:1986 卷标:108(22) 页码:7117-19]

7306-46-9 + 102922-34-9 = 85-63-2 [标题:Reaction Conditions
标题:Product Subclass 21: α-Lithioamines
作者:Gawley,Robert E.; Et Al
参考文献:Science Of Synthesis 日期:2006 卷标:8 页码:677-757]

116071-85-3 = 85-63-2
反应条件:1.1 Reagents: Hydrazine2.1 -2.2 Reagents: Lithium Aluminum Hydride
标题:Synthesis Of R-Laudanosine And 9-R-O-Methylflavinantine By Asymmetric Alkylation
作者:Gawley,Robert E.; Et Al
参考文献:Tetrahedron Letters 日期:1988 卷标:29(3) 页码:301-2]

= 85-63-2
反应条件:1.1 Reagents: Hydrochloric Acid Solvents: Dichloromethane; 24 H,Rt2.1 Reagents: Sodium Acetate,Zinc Chloride,Sodium Cyanoborohydride Solvents: Methanol; 24 H,Rt
标题:Organocatalytic Enantioselective Pictet-Spengler Approach To Biologically Relevant 1-Benzyl-1,2,3,4-Tetrahydroisoquinoline Alkaloids
作者:Ruiz-Olalla,Andrea; Et Al
参考文献:Journal Of Organic Chemistry 日期:2015 卷标:80(10) 页码:5125-5132]

321670-13-7 = 85-63-2
反应条件:1.1 Reagents: Sodium Acetate,Pyridinium Chlorochromate Solvents: Dichloromethane1.2 Reagents: Sodium Hydroxide1.3 Solvents: Chloroform1.4 Reagents: Potassium Hydroxide Solvents: Methanol,Tetrahydrofuran1.5 Reagents: Hydrochloric Acid1.6 Solvents: Diethyl Ether1.7 Reagents: Sodium Hydroxide1.8 Solvents: Chloroform2.1 Solvents: Dichloromethane2.2 Reagents: Lithium Aluminum Hydride Solvents: Diethyl Ether2.3 Reagents: Sodium Hydroxide Solvents: Water
标题:A Novel Straightforward Synthesis Of Enantiopure Tetrahydroisoquinoline Alkaloids
作者:Pedrosa,Rafael; Et Al
参考文献:Journal Of Organic Chemistry 日期:2001 卷标:66(1) 页码:243-250]

5703-21-9 + 35690-71-2 = 85-63-2
反应条件:1.1 Catalysts: 2850240-94-5 Solvents: Chloroform; 40 H,Rt1.2 Reagents: Triethylamine; Rt2.1 Reagents: Diisobutylaluminum Hydride Solvents: Toluene,Tetrahydrofuran; 0 °C; 0 °C -> Rt; 1 H,Rt2.2 Reagents: Potassium Sodium Tartrate Solvents: Water; 30 Min,Rt
标题:A Catalytic Asymmetric Pictet-Spengler Platform As A Biomimetic Diversification Strategy Toward Naturally Occurring Alkaloids
作者:Scharf,Manuel J.; Et Al
参考文献:Journal Of The American Chemical Society 日期:2022 卷标:144(34) 页码:15451-15456

3,4-二氢罂粟碱置于1.) δ-(R)-1 吡啶,Lithium Aluminium Tetrahydride,氢气体系中,化学反应生成阿曲库铵杂质n
参考文献:Asymmetric Synthesis Of Isoquinoline Alkaloids By Homogeneous Catalysis
标题:Asymmetric Synthesis Of Isoquinoline Alkaloids By Homogeneous Catalysis
摘要:
DOI:10.1021/ja00282A054

海关参考信息

2902600000-乙苯
2905110000-甲醇
2907210001-间苯二酚
2908199090-其他酚的卤化衍生物
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专利信息

专利号:US-2024091733-A1
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权利人:ODH IP CORP
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