84-39-9 (刺罂粟碱,(12bS)-6,7,12b,13-tetrahydro-4H-[1,3]dioxolo[4,5-g][1,3]dioxolo[7,8]isoquino[3,2-a]isoquinoline)

快速询单

结构式：

刺罂粟碱MOL文件

CAS号：

84-39-9

中文名称：

刺罂粟碱

英文名称：

(12bS)-6,7,12b,13-tetrahydro-4H-[1,3]dioxolo[4,5-g][1,3]dioxolo[7,8]isoquino[3,2-a]isoquinoline

分子式：

C₁₉H₁₇NO₄

分子量：

323.342585325241

植物源：

虞美人

刺罂粟碱(84-39-9)名称与标识符

名称

中文别名：

金罂粟碱;刺罂粟碱;人血草碱;

英文别名：

(12bS)-6,7,12b,13-tetrahydro-4H-[1,3]dioxolo[4,5-g][1,3]dioxolo[7,8]isoquino[3,2-a]isoquinoline;Stylopine;STYLOPINE, (-)-(P);(+/-)-7,8,13,13a-tetrahydrocoptisine;(+/-)stylopine;(+/-)-stylopine;dl-Tetrahydrocoptisine;tetrahydrocoptisine;2,3:9,10-Bis(methylenedioxy)-(-)-tetrahydroberberine;Stylopin;l-Stylopine;l-Tetrahydrocoptisine;(12bS)-6,7,12b,13-Tetrahydro-4H-bis[1,3]benzodioxolo[5,6-a:4',5'-g]quinolizine;(12bS)-6,7,12b,13-Tetrahydro-4H-bis[1,3]benzodioxolo[5,6-a:4′,5′-g]quinolizine (ACI);13aα-Berbine, 2,3:9,10-bis(methylenedioxy)- (8CI);4H-Bis[1,3]benzodioxolo[5,6-a:4′,5′-g]quinolizine, 6,7,12b,13-tetrahydro-, (S)- (ZCI);(-)-Stylopine;(-)-Tetrahydrocoptisine;(S)-(-)-Stylopine;(S)-Stylopine;Stylopine, (-)-;Q27102969;(12bS)-6,7,12b,13-tetrahydro-2H,4H,10H-(1,3)dioxolo(4,5-g)(1,3)dioxolo(4',5':7,8)isoquino(3,2-a)isoquinoline;HY-N0924B;C05175;(1S)-5,7,17,19-tetraoxa-13-azahexacyclo[11.11.0.02,10.04,8.015,23.016,20]tetracosa-2,4(8),9,15(23),16(20),21-hexaene;CS-0083712;2,3:9,10-Bis(methylenedioxy)-13a-alpha-berbine;6,7,12b,13e-Tetrahydro-4H-bis(1,3)benzodioxolo(5,6-a:4',5'-g)quinolizine;13Aalpha-BERBINE, 2,3:9,10-BIS(METHYLENEDIOXY)-;6, 7, 12b, 13e-tetrahydro-4H-bis [1, 3]benzodioxolo[5, 6-a:4' , 5' -g] quinolizine;STYLOPINE, (+/-)-(P);stylopine, (S)-isomer;84-39-9;6,7,12b,13e-Tetrahydro-4H-bis[1,3]benzodioxolo[5,6-a:4',5'-g]quinolizine;DTXSID001004259;NS00094097;4H-Bis(1,3)benzodioxolo(5,6-a:4',5'-g)quinolizine, 6,7,12b,13-tetrahydro-, (S)-;CHEMBL1922602;(-)-Stylopine (Tetrahydrocoptisine);CHEBI:18285;NSC-110382;(12bS)-6,7,12b,13-tetrahydro-2H,4H,10H-[1,3]dioxolo[4,5-g][1,3]dioxolo[4',5':7,8]isoquino[3,2-a]isoquinoline;4H-BIS(1,3)BENZODIOXOLO(5,6-A:4',5'-G)QUINOLIZINE, 6,7,12B,13-TETRAHYDRO-, (12BS)-;6,7,12b,13-Tetrahydro-2H,4H,10H-[1,3]dioxolo[4,5-g][1,3]dioxolo[7,8]isoquinolino[3,2-a]isoquinoline;SCHEMBL18891073;6, 7, 12b, 13e-tetrahydro-4H-bis (1, 3)benzodioxolo(5, 6-a:4', 5'-g) quinolizine;(12bS)-6,7,12b,13-Tetrahydro-4H-bis(1,3)benzodioxolo(5,6-a:4',5'-g)quinolizine;(+)-Stylopine;J0JS75Q12Z;AKOS000277993;FS-7018;AKOS016023688;STYLOPINE [MI];13a-alpha-BERBINE, 2,3:9,10-BIS(METHYLENEDIOXY)-;Stylopine (VAN);13A.ALPHA.-BERBINE, 2,3:9,10-BIS(METHYLENEDIOXY)-;Coptisine, tetrahydro-;NSC 404529;(S)-Stylopin;UNII-J0JS75Q12Z;Berbine, 2,3:9,10-bis(methylenedioxy)-, (+-)-;SCHEMBL14703887;(+-)-Stylopine;NSC 110382;(R)-stylopine;(1R)-5,7,17,19-tetraoxa-13-azahexacyclo[11.11.0.02,10.04,8.015,23.016,20]tetracosa-2,4(8),9,15(23),16(20),21-hexaene;NS00094094;4H-Bis(1,3)benzodioxolo(5,6-a:4',5'-g)quinolizine, 6,7,12b,13-tetrahydro-;4H-Bis(1,3)benzodioxolo(5,6-a:4',5'-g)quinolizine, 6,7,12b,13-tetrahydro-, (+-)-;Q27280991;(+-)-Tetrahydrocoptisine;DA-78066;

标识符

InChIKey：

UXYJCYXWJGAKQY-HNNXBMFYSA-N

Inchi：

1S/C19H17NO4/c1-2-16-19(24-10-21-16)14-8-20-4-3-12-6-17-18(23-9-22-17)7-13(12)15(20)5-11(1)14/h1-2,6-7,15H,3-5,8-10H2/t15-/m0/s1

SMILES：

[C@@H]12CC3C=CC4OCOC=4C=3CN1CCC1=CC3OCOC=3C=C21

刺罂粟碱(84-39-9)物化性质

实验特性

LogP : 2.73740
PSA : 40.16000
折射率 : 1.722
沸点 : 466.6°C at 760 mmHg
熔点 : 206-207 ºC
蒸气压 : 0.0±1.2 mmHg at 25°C
闪点 : 142.5°C
溶解度 : Insuluble (3.9E-3 g/L) (25 ºC),
颜色与性状 : Powder
密度 : 1.47±0.1 g/cm3 (20 ºC 760 Torr),

计算特性

精确分子量 : 323.11600
氢键供体数量 : 0
氢键受体数量 : 5
可旋转化学键数量 : 0
同位素质量 : 323.116
重原子数量 : 24
复杂度 : 502
同位素原子数量 : 0
确定原子立构中心数量 : 1
不确定原子立构中心数量 : 0
确定化学键立构中心数量 : 0
不确定化学键立构中心数量 : 0
共价键单元数量 : 1
疏水参数计算参考值（XlogP） : 3
拓扑分子极性表面积 : 40.2A^2

刺罂粟碱(84-39-9)安全信息

安全说明： H303+H313+H333
危险品运输编号： 1544
危害声明：H303吞入可能有害+H313皮肤接触可能有害+H333吸入可能对身体有害
警示性声明：P264+P280+P305+P351+P338+P337+P313
储存条件： 4℃条件下存储，-4℃条件下存储更佳
PackingGroup： III
HazardClass： 6.1(b)

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刺罂粟碱(84-39-9)合成路线

合成路线：1 步

19716-61-1

_70%

84-39-9

反应条件：

1.1 Reagents: Lithium aluminum hydride Catalysts: Aluminum chloride Solvents: Diethyl ether ; 0.5 h, 0 °C → rt
1.2 2 h, rt → reflux
1.3 Reagents: Sodium hydroxide Solvents: Water ; reflux
1.4 Reagents: Formic acid , Triethylamine Catalysts: [N-[(1S,2S)-2-(Amino-κN)-1,2-diphenylethyl]-4-methylbenzenesulfonamidato-κN]chlo… Solvents: Dichloromethane ; 40 h, rt
1.5 Reagents: Sodium bicarbonate Solvents: Water ; rt

参考文献：

Evolution of two routes for asymmetric total synthesis of tetrahydroprotoberberine alkaloids

Yu, Jingxun; et al, Organic Chemistry Frontiers, 2018, 5(2), 242-246

合成路线：1 步

53777-78-9

_47%

84-39-9

反应条件：

1.1 Reagents: Hydrogen Solvents: Dichloromethane
1.2 Reagents: Potassium bromide Catalysts: Di-μ-chlorobis[(1,2,5,6-η)-1,5-cyclooctadiene]diiridium , 1,1′-Bis[(11bS)-3,5-dihydro-4H-dinaphtho[2,1-c:1′,2′-e]phosphepin-4-yl]ferrocene Solvents: Acetic acid , Dichloromethane ; 7.5 min, 40 bar, 80 °C

参考文献：

Development of a Fully Continuous-Flow Approach Towards Asymmetric Total Synthesis of Tetrahydroprotoberberine Natural Alkaloids

Li, Weijian; et al, Chemistry - A European Journal, 2022, 28(33),

合成路线：1 步

53777-78-9

84-39-9

反应条件：

1.1 Reagents: Formic acid , Triethylamine Catalysts: [N-[(1S,2S)-2-(Amino-κN)-1,2-diphenylethyl]-4-methylbenzenesulfonamidato-κN]chlo… Solvents: Dichloromethane ; 40 h, rt
1.2 Reagents: Sodium bicarbonate Solvents: Water ; rt

参考文献：

Evolution of two routes for asymmetric total synthesis of tetrahydroprotoberberine alkaloids

Yu, Jingxun; et al, Organic Chemistry Frontiers, 2018, 5(2), 242-246

合成路线：1 步

3486-66-6

84-39-9

反应条件：

参考文献：

Evolution of two routes for asymmetric total synthesis of tetrahydroprotoberberine alkaloids

Yu, Jingxun; et al, Organic Chemistry Frontiers, 2018, 5(2), 242-246

合成路线：1 步

483-34-1

84-39-9

反应条件：

1.1 Reagents: NADPH Catalysts: Synthase, (S)-stylopine (Eschscholzia californica clone #31 gene CYP719A3) Solvents: Water ; 30 min, pH 7.6, 30 °C
1.2 Reagents: Trichloroacetic acid Solvents: Water

参考文献：

Molecular cloning and characterization of methylenedioxy bridge-forming enzymes involved in stylopine biosynthesis in Eschscholzia californica

Ikezawa, Nobuhiro; et al, FEBS Journal, 2007, 274(4), 1019-1035

合成路线：2 步

2827003-73-4

534-15-6

84-39-9

反应条件：

1.1 Solvents: Formic acid ; 7.5 min, 80 °C
1.2 Reagents: Sulfuric acid magnesium salt (1:1) Solvents: Formic acid , Water ; 0 °C; 1 h, 0 °C → rt; 2.5 min, 120 °C
1.3 Reagents: Sodium hydroxide Solvents: Water ; pH 10
2.1 Reagents: Hydrogen Solvents: Dichloromethane
2.2 Reagents: Potassium bromide Catalysts: Di-μ-chlorobis[(1,2,5,6-η)-1,5-cyclooctadiene]diiridium , 1,1′-Bis[(11bS)-3,5-dihydro-4H-dinaphtho[2,1-c:1′,2′-e]phosphepin-4-yl]ferrocene Solvents: Acetic acid , Dichloromethane ; 7.5 min, 40 bar, 80 °C

参考文献：

Development of a Fully Continuous-Flow Approach Towards Asymmetric Total Synthesis of Tetrahydroprotoberberine Natural Alkaloids

Li, Weijian; et al, Chemistry - A European Journal, 2022, 28(33),

合成路线：3 步

355816-19-2

84-39-9

反应条件：

1.1 Reagents: Hydrochloric acid Catalysts: Palladium Solvents: Methanol , tert-Butyl methyl ether ; 5 min, 25 °C
2.1 Solvents: Formic acid ; 7.5 min, 80 °C
2.2 Reagents: Sulfuric acid magnesium salt (1:1) Solvents: Formic acid , Water ; 0 °C; 1 h, 0 °C → rt; 2.5 min, 120 °C
2.3 Reagents: Sodium hydroxide Solvents: Water ; pH 10
3.1 Reagents: Hydrogen Solvents: Dichloromethane
3.2 Reagents: Potassium bromide Catalysts: Di-μ-chlorobis[(1,2,5,6-η)-1,5-cyclooctadiene]diiridium , 1,1′-Bis[(11bS)-3,5-dihydro-4H-dinaphtho[2,1-c:1′,2′-e]phosphepin-4-yl]ferrocene Solvents: Acetic acid , Dichloromethane ; 7.5 min, 40 bar, 80 °C

参考文献：

Development of a Fully Continuous-Flow Approach Towards Asymmetric Total Synthesis of Tetrahydroprotoberberine Natural Alkaloids

Li, Weijian; et al, Chemistry - A European Journal, 2022, 28(33),