86264-76-8 (氨柔比星中间体,N-[(2R)-5,12-Dihydroxy-2-(2-methyl-1,3-dioxolan-2-yl)-6,11-dioxo-3,4-dihydro-1H-tetracen-2-yl]acetamide)

快速询单

结构式：

氨柔比星中间体MOL文件

CAS号：

86264-76-8

中文名称：

氨柔比星中间体

英文名称：

N-[(2R)-5,12-Dihydroxy-2-(2-methyl-1,3-dioxolan-2-yl)-6,11-dioxo-3,4-dihydro-1H-tetracen-2-yl]acetamide

分子式：

C₂₄H₂₃NO₇

分子量：

437.441927194595

氨柔比星中间体(86264-76-8)名称与标识符

名称

中文别名：

氨柔比星中间体;

英文别名：

(R)-N-(5,12-dihydroxy-2-(2-methyl-1,3-dioxolan-2-yl)-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-2-yl)acetamide;(R)-(-)-9-acetamido-9-<1,1-(ethylenedioxy)ethyl>-6,11-dihydroxy-7,8,9,10-tetrahydro-5,12-naphthacenedione;N-[(2R)-5,12-Dihydroxy-2-(2-methyl-1,3-dioxolan-2-yl)-6,11-dioxo-3,4-dihydro-1H-tetracen-2-yl]acetam;F52832;Acetamide, N-[1,2,3,4,6,11-hexahydro-5,12-dihydroxy-2-(2-methyl-1,3-dioxolan-2-yl)-6,11-dioxo-2-naphthacenyl]-, (R)- (9CI);86264-76-8;AS-74936;AKOS037647827;N-[(2R)-5,12-dihydroxy-2-(2-methyl-1,3-dioxolan-2-yl)-6,11-dioxo-3,4-dihydro-1H-tetracen-2-yl]acetamide;N-[(2R)-5,12-dihydroxy-2-(2-methyl-1,3-dioxolan-2-yl)-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-2-yl]acetamide;

标识符

MDL：

MFCD18072725

InChIKey：

QDFKHJVKZRGRBA-XMMPIXPASA-N

Inchi：

1S/C24H23NO7/c1-12(26)25-24(23(2)31-9-10-32-23)8-7-15-16(11-24)22(30)18-17(21(15)29)19(27)13-5-3-4-6-14(13)20(18)28/h3-6,29-30H,7-11H2,1-2H3,(H,25,26)/t24-/m1/s1

SMILES：

O1CCOC1(C)[C@@]1(CC2C(=C3C(C4C=CC=CC=4C(C3=C(C=2CC1)O)=O)=O)O)NC(C)=O

氨柔比星中间体(86264-76-8)物化性质

实验特性

LogP : 2.39070
PSA : 122.16000

计算特性

精确分子量 : 437.14745207g/mol
氢键供体数量 : 3
氢键受体数量 : 7
可旋转化学键数量 : 2
同位素质量 : 437.14745207g/mol
重原子数量 : 32
复杂度 : 808
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） : 2.9
拓扑分子极性表面积 : 122

氨柔比星中间体(86264-76-8)推荐厂家更多厂家(6)

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氨柔比星中间体(86264-76-8)合成路线

合成路线：1 步

104319-02-0

107-21-1

_81%

86264-76-8

反应条件：

1.1 Catalysts: p-Toluenesulfonic acid Solvents: Toluene ; 4 h, rt → reflux

参考文献：

Synthesis of (+)-9-amino-4-demethoxy-9-deoxydaunomycinone

Li, Zhiyu; et al, Zhongguo Yiyao Gongye Zazhi, 2009, 40(11), 805-809

合成路线：1 步

104319-02-0

107-21-1

86264-76-8

反应条件：

1.1 Catalysts: p-Toluenesulfonic acid Solvents: Toluene

参考文献：

Stereospecific total synthesis of 9-aminoanthracyclines: (+)-9-amino-9-deoxydaunomycin and related compounds

Ishizumi, Kikuo; et al, Journal of Organic Chemistry, 1987, 52(20), 4477-85

合成路线：2 步

110204-84-7

86264-76-8

反应条件：

1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol , Ethyl acetate
2.1 Catalysts: p-Toluenesulfonic acid Solvents: Toluene

参考文献：

Stereospecific total synthesis of 9-aminoanthracyclines: (+)-9-amino-9-deoxydaunomycin and related compounds

Ishizumi, Kikuo; et al, Journal of Organic Chemistry, 1987, 52(20), 4477-85

合成路线：2 步

86264-61-1

85-44-9

86264-76-8

反应条件：

1.1 Reagents: Aluminum chloride , Sodium chloride
1.2 Reagents: Oxalic acid Solvents: Water
1.3 Solvents: Toluene
2.1 Catalysts: p-Toluenesulfonic acid Solvents: Toluene

参考文献：

Stereospecific total synthesis of 9-aminoanthracyclines: (+)-9-amino-9-deoxydaunomycin and related compounds

Ishizumi, Kikuo; et al, Journal of Organic Chemistry, 1987, 52(20), 4477-85

合成路线：2 步

86264-61-1

93-97-0

86264-76-8

反应条件：

1.1 Reagents: Sodium chloride Catalysts: Aluminum chloride ; rt → 135 °C; 30 min, 130 - 135 °C
1.2 Reagents: Oxalic acid Solvents: Water ; 1 h, 50 - 60 °C
2.1 Catalysts: p-Toluenesulfonic acid Solvents: Toluene ; 4 h, rt → reflux

参考文献：

Synthesis of (+)-9-amino-4-demethoxy-9-deoxydaunomycinone

Li, Zhiyu; et al, Zhongguo Yiyao Gongye Zazhi, 2009, 40(11), 805-809

合成路线：3 步

110267-80-6

108-24-7

86264-76-8

反应条件：

1.1 Reagents: Pyridine Catalysts: 4-(Dimethylamino)pyridine Solvents: Dichloromethane
2.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol , Ethyl acetate
3.1 Catalysts: p-Toluenesulfonic acid Solvents: Toluene

参考文献：

Stereospecific total synthesis of 9-aminoanthracyclines: (+)-9-amino-9-deoxydaunomycin and related compounds

Ishizumi, Kikuo; et al, Journal of Organic Chemistry, 1987, 52(20), 4477-85

合成路线：3 步

110267-84-0

108-24-7

86264-76-8

反应条件：

1.1 Reagents: Sodium hydroxide , Zinc Solvents: Water ; rt → 65 °C; 65 °C; 1 h, 65 °C
1.2 Solvents: Toluene ; 65 °C; 2 h, 65 °C
1.3 Reagents: Hydrochloric acid Solvents: Water ; pH 9
1.4 Reagents: Pyridine ; 1 h, rt; rt → 5 °C
2.1 Reagents: Sodium chloride Catalysts: Aluminum chloride ; rt → 135 °C; 30 min, 130 - 135 °C
2.2 Reagents: Oxalic acid Solvents: Water ; 1 h, 50 - 60 °C
3.1 Catalysts: p-Toluenesulfonic acid Solvents: Toluene ; 4 h, rt → reflux

参考文献：

Synthesis of (+)-9-amino-4-demethoxy-9-deoxydaunomycinone

Li, Zhiyu; et al, Zhongguo Yiyao Gongye Zazhi, 2009, 40(11), 805-809

合成路线：3 步

110267-86-2

108-24-7

86264-76-8

反应条件：

1.1 Reagents: Pyridine Solvents: Toluene
2.1 Reagents: Aluminum chloride , Sodium chloride
2.2 Reagents: Oxalic acid Solvents: Water
2.3 Solvents: Toluene
3.1 Catalysts: p-Toluenesulfonic acid Solvents: Toluene

参考文献：

Stereospecific total synthesis of 9-aminoanthracyclines: (+)-9-amino-9-deoxydaunomycin and related compounds

Ishizumi, Kikuo; et al, Journal of Organic Chemistry, 1987, 52(20), 4477-85

合成路线：3 步

110267-85-1

86264-76-8

反应条件：

1.1 Reagents: Aluminum alloy, nonbase, Al,Hg Solvents: Tetrahydrofuran , Water
2.1 Reagents: Aluminum chloride , Sodium chloride
2.2 Reagents: Oxalic acid Solvents: Water
2.3 Solvents: Toluene
3.1 Catalysts: p-Toluenesulfonic acid Solvents: Toluene

参考文献：

Stereospecific total synthesis of 9-aminoanthracyclines: (+)-9-amino-9-deoxydaunomycin and related compounds

Ishizumi, Kikuo; et al, Journal of Organic Chemistry, 1987, 52(20), 4477-85

合成路线：4 步

110267-79-3

92395-41-0

86264-76-8

反应条件：

1.1 Reagents: Tetramethylurea , Silver triflate Solvents: Diethyl ether , Dichloromethane
2.1 Reagents: Pyridine Catalysts: 4-(Dimethylamino)pyridine Solvents: Dichloromethane
3.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol , Ethyl acetate
4.1 Catalysts: p-Toluenesulfonic acid Solvents: Toluene

参考文献：

Stereospecific total synthesis of 9-aminoanthracyclines: (+)-9-amino-9-deoxydaunomycin and related compounds

Ishizumi, Kikuo; et al, Journal of Organic Chemistry, 1987, 52(20), 4477-85

合成路线：4 步

110267-84-0

86264-76-8

反应条件：

1.1 Reagents: Sodium hydroxide , Zinc Solvents: Toluene , Water
2.1 Reagents: Pyridine Solvents: Toluene
3.1 Reagents: Aluminum chloride , Sodium chloride
3.2 Reagents: Oxalic acid Solvents: Water
3.3 Solvents: Toluene
4.1 Catalysts: p-Toluenesulfonic acid Solvents: Toluene

参考文献：

Stereospecific total synthesis of 9-aminoanthracyclines: (+)-9-amino-9-deoxydaunomycin and related compounds

Ishizumi, Kikuo; et al, Journal of Organic Chemistry, 1987, 52(20), 4477-85

合成路线：4 步

67-68-5

86264-57-5

86264-76-8

反应条件：

1.1 Reagents: Sodium hydride Solvents: Tetrahydrofuran
1.2 Solvents: Tetrahydrofuran
2.1 Reagents: Aluminum alloy, nonbase, Al,Hg Solvents: Tetrahydrofuran , Water
3.1 Reagents: Aluminum chloride , Sodium chloride
3.2 Reagents: Oxalic acid Solvents: Water
3.3 Solvents: Toluene
4.1 Catalysts: p-Toluenesulfonic acid Solvents: Toluene

参考文献：

Stereospecific total synthesis of 9-aminoanthracyclines: (+)-9-amino-9-deoxydaunomycin and related compounds

Ishizumi, Kikuo; et al, Journal of Organic Chemistry, 1987, 52(20), 4477-85

合成路线：4 步

67-68-5

99907-83-2

86264-76-8

反应条件：

1.1 Reagents: Sodium hydride Solvents: Tetrahydrofuran ; 1.5 h, rt → 65 °C; 65 °C → 10 °C; 5 - 10 °C
1.2 Solvents: Tetrahydrofuran ; 5 - 10 °C; 1 h, 5 - 10 °C
1.3 Reagents: Hydrochloric acid Solvents: Water ; pH 2.5
1.4 Reagents: Sodium hydroxide Solvents: Water
2.1 Reagents: Sodium hydroxide , Zinc Solvents: Water ; rt → 65 °C; 65 °C; 1 h, 65 °C
2.2 Solvents: Toluene ; 65 °C; 2 h, 65 °C
2.3 Reagents: Hydrochloric acid Solvents: Water ; pH 9
2.4 Reagents: Pyridine ; 1 h, rt; rt → 5 °C
3.1 Reagents: Sodium chloride Catalysts: Aluminum chloride ; rt → 135 °C; 30 min, 130 - 135 °C
3.2 Reagents: Oxalic acid Solvents: Water ; 1 h, 50 - 60 °C
4.1 Catalysts: p-Toluenesulfonic acid Solvents: Toluene ; 4 h, rt → reflux

参考文献：

Synthesis of (+)-9-amino-4-demethoxy-9-deoxydaunomycinone

Li, Zhiyu; et al, Zhongguo Yiyao Gongye Zazhi, 2009, 40(11), 805-809

合成路线：5 步

67-68-5

99907-83-2

86264-76-8

反应条件：

1.1 Reagents: Sodium hydride Solvents: Tetrahydrofuran
1.2 Solvents: Tetrahydrofuran
2.1 Reagents: Sodium hydroxide , Zinc Solvents: Toluene , Water
3.1 Reagents: Pyridine Solvents: Toluene
4.1 Reagents: Aluminum chloride , Sodium chloride
4.2 Reagents: Oxalic acid Solvents: Water
4.3 Solvents: Toluene
5.1 Catalysts: p-Toluenesulfonic acid Solvents: Toluene

参考文献：

Stereospecific total synthesis of 9-aminoanthracyclines: (+)-9-amino-9-deoxydaunomycin and related compounds

Ishizumi, Kikuo; et al, Journal of Organic Chemistry, 1987, 52(20), 4477-85

合成路线：5 步

110267-78-2

86264-76-8

反应条件：

1.1 Reagents: Sulfuric acid Solvents: Water
2.1 Reagents: Tetramethylurea , Silver triflate Solvents: Diethyl ether , Dichloromethane
3.1 Reagents: Pyridine Catalysts: 4-(Dimethylamino)pyridine Solvents: Dichloromethane
4.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol , Ethyl acetate
5.1 Catalysts: p-Toluenesulfonic acid Solvents: Toluene

参考文献：

Stereospecific total synthesis of 9-aminoanthracyclines: (+)-9-amino-9-deoxydaunomycin and related compounds

Ishizumi, Kikuo; et al, Journal of Organic Chemistry, 1987, 52(20), 4477-85

合成路线：5 步

86264-55-3

86264-76-8

反应条件：

1.1 Reagents: Sulfuric acid Solvents: Methanol
2.1 Reagents: Sodium hydride Solvents: Tetrahydrofuran
2.2 Solvents: Tetrahydrofuran
3.1 Reagents: Aluminum alloy, nonbase, Al,Hg Solvents: Tetrahydrofuran , Water
4.1 Reagents: Aluminum chloride , Sodium chloride
4.2 Reagents: Oxalic acid Solvents: Water
4.3 Solvents: Toluene
5.1 Catalysts: p-Toluenesulfonic acid Solvents: Toluene

参考文献：

Stereospecific total synthesis of 9-aminoanthracyclines: (+)-9-amino-9-deoxydaunomycin and related compounds

Ishizumi, Kikuo; et al, Journal of Organic Chemistry, 1987, 52(20), 4477-85

合成路线：5 步

95585-77-6

86264-76-8

反应条件：

1.1 Reagents: Bromotrimethylsilane Solvents: Chloroform
2.1 Reagents: Tetramethylurea , Silver triflate Solvents: Diethyl ether , Dichloromethane
3.1 Reagents: Pyridine Catalysts: 4-(Dimethylamino)pyridine Solvents: Dichloromethane
4.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol , Ethyl acetate
5.1 Catalysts: p-Toluenesulfonic acid Solvents: Toluene

参考文献：

Stereospecific total synthesis of 9-aminoanthracyclines: (+)-9-amino-9-deoxydaunomycin and related compounds

Ishizumi, Kikuo; et al, Journal of Organic Chemistry, 1987, 52(20), 4477-85

合成路线：5 步

99907-80-9

86264-76-8

反应条件：

1.1 Reagents: (-)-Mandelic acid Solvents: Isopropanol , Toluene ; 3 h, rt
1.2 Reagents: Sodium carbonate Solvents: Water ; rt
2.1 Reagents: Sodium hydride Solvents: Tetrahydrofuran ; 1.5 h, rt → 65 °C; 65 °C → 10 °C; 5 - 10 °C
2.2 Solvents: Tetrahydrofuran ; 5 - 10 °C; 1 h, 5 - 10 °C
2.3 Reagents: Hydrochloric acid Solvents: Water ; pH 2.5
2.4 Reagents: Sodium hydroxide Solvents: Water
3.1 Reagents: Sodium hydroxide , Zinc Solvents: Water ; rt → 65 °C; 65 °C; 1 h, 65 °C
3.2 Solvents: Toluene ; 65 °C; 2 h, 65 °C
3.3 Reagents: Hydrochloric acid Solvents: Water ; pH 9
3.4 Reagents: Pyridine ; 1 h, rt; rt → 5 °C
4.1 Reagents: Sodium chloride Catalysts: Aluminum chloride ; rt → 135 °C; 30 min, 130 - 135 °C
4.2 Reagents: Oxalic acid Solvents: Water ; 1 h, 50 - 60 °C
5.1 Catalysts: p-Toluenesulfonic acid Solvents: Toluene ; 4 h, rt → reflux

参考文献：

Synthesis of (+)-9-amino-4-demethoxy-9-deoxydaunomycinone

Li, Zhiyu; et al, Zhongguo Yiyao Gongye Zazhi, 2009, 40(11), 805-809

合成路线：6 步

99907-84-3

67-56-1

86264-76-8

反应条件：

1.1 Reagents: Hydrochloric acid Solvents: Methanol ; cooled; 10 h, reflux
1.2 Reagents: Sodium bicarbonate Solvents: Water ; pH 8 - 9
2.1 Reagents: (-)-Mandelic acid Solvents: Isopropanol , Toluene ; 3 h, rt
2.2 Reagents: Sodium carbonate Solvents: Water ; rt
3.1 Reagents: Sodium hydride Solvents: Tetrahydrofuran ; 1.5 h, rt → 65 °C; 65 °C → 10 °C; 5 - 10 °C
3.2 Solvents: Tetrahydrofuran ; 5 - 10 °C; 1 h, 5 - 10 °C
3.3 Reagents: Hydrochloric acid Solvents: Water ; pH 2.5
3.4 Reagents: Sodium hydroxide Solvents: Water
4.1 Reagents: Sodium hydroxide , Zinc Solvents: Water ; rt → 65 °C; 65 °C; 1 h, 65 °C
4.2 Solvents: Toluene ; 65 °C; 2 h, 65 °C
4.3 Reagents: Hydrochloric acid Solvents: Water ; pH 9
4.4 Reagents: Pyridine ; 1 h, rt; rt → 5 °C
5.1 Reagents: Sodium chloride Catalysts: Aluminum chloride ; rt → 135 °C; 30 min, 130 - 135 °C
5.2 Reagents: Oxalic acid Solvents: Water ; 1 h, 50 - 60 °C
6.1 Catalysts: p-Toluenesulfonic acid Solvents: Toluene ; 4 h, rt → reflux

参考文献：

Synthesis of (+)-9-amino-4-demethoxy-9-deoxydaunomycinone

Li, Zhiyu; et al, Zhongguo Yiyao Gongye Zazhi, 2009, 40(11), 805-809

合成路线：7 步

1373557-92-6

86264-76-8

反应条件：

1.1 Reagents: Barium hydroxide Solvents: Water ; 36 h, rt → reflux; reflux → rt
1.2 Reagents: Sulfuric acid Solvents: Water ; pH 3
1.3 Reagents: Triethylamine ; pH 6
2.1 Reagents: Hydrochloric acid Solvents: Methanol ; cooled; 10 h, reflux
2.2 Reagents: Sodium bicarbonate Solvents: Water ; pH 8 - 9
3.1 Reagents: (-)-Mandelic acid Solvents: Isopropanol , Toluene ; 3 h, rt
3.2 Reagents: Sodium carbonate Solvents: Water ; rt
4.1 Reagents: Sodium hydride Solvents: Tetrahydrofuran ; 1.5 h, rt → 65 °C; 65 °C → 10 °C; 5 - 10 °C
4.2 Solvents: Tetrahydrofuran ; 5 - 10 °C; 1 h, 5 - 10 °C
4.3 Reagents: Hydrochloric acid Solvents: Water ; pH 2.5
4.4 Reagents: Sodium hydroxide Solvents: Water
5.1 Reagents: Sodium hydroxide , Zinc Solvents: Water ; rt → 65 °C; 65 °C; 1 h, 65 °C
5.2 Solvents: Toluene ; 65 °C; 2 h, 65 °C
5.3 Reagents: Hydrochloric acid Solvents: Water ; pH 9
5.4 Reagents: Pyridine ; 1 h, rt; rt → 5 °C
6.1 Reagents: Sodium chloride Catalysts: Aluminum chloride ; rt → 135 °C; 30 min, 130 - 135 °C
6.2 Reagents: Oxalic acid Solvents: Water ; 1 h, 50 - 60 °C
7.1 Catalysts: p-Toluenesulfonic acid Solvents: Toluene ; 4 h, rt → reflux

参考文献：

Synthesis of (+)-9-amino-4-demethoxy-9-deoxydaunomycinone

Li, Zhiyu; et al, Zhongguo Yiyao Gongye Zazhi, 2009, 40(11), 805-809

合成路线：8 步

37464-90-7

151-50-8

86264-76-8

反应条件：

1.1 Reagents: Ammonium carbonate Solvents: Ethanol , Water ; 3 h, rt → reflux; cooled
2.1 Reagents: Barium hydroxide Solvents: Water ; 36 h, rt → reflux; reflux → rt
2.2 Reagents: Sulfuric acid Solvents: Water ; pH 3
2.3 Reagents: Triethylamine ; pH 6
3.1 Reagents: Hydrochloric acid Solvents: Methanol ; cooled; 10 h, reflux
3.2 Reagents: Sodium bicarbonate Solvents: Water ; pH 8 - 9
4.1 Reagents: (-)-Mandelic acid Solvents: Isopropanol , Toluene ; 3 h, rt
4.2 Reagents: Sodium carbonate Solvents: Water ; rt
5.1 Reagents: Sodium hydride Solvents: Tetrahydrofuran ; 1.5 h, rt → 65 °C; 65 °C → 10 °C; 5 - 10 °C
5.2 Solvents: Tetrahydrofuran ; 5 - 10 °C; 1 h, 5 - 10 °C
5.3 Reagents: Hydrochloric acid Solvents: Water ; pH 2.5
5.4 Reagents: Sodium hydroxide Solvents: Water
6.1 Reagents: Sodium hydroxide , Zinc Solvents: Water ; rt → 65 °C; 65 °C; 1 h, 65 °C
6.2 Solvents: Toluene ; 65 °C; 2 h, 65 °C
6.3 Reagents: Hydrochloric acid Solvents: Water ; pH 9
6.4 Reagents: Pyridine ; 1 h, rt; rt → 5 °C
7.1 Reagents: Sodium chloride Catalysts: Aluminum chloride ; rt → 135 °C; 30 min, 130 - 135 °C
7.2 Reagents: Oxalic acid Solvents: Water ; 1 h, 50 - 60 °C
8.1 Catalysts: p-Toluenesulfonic acid Solvents: Toluene ; 4 h, rt → reflux

参考文献：

Synthesis of (+)-9-amino-4-demethoxy-9-deoxydaunomycinone

Li, Zhiyu; et al, Zhongguo Yiyao Gongye Zazhi, 2009, 40(11), 805-809