867267-28-5 (5-羟基-2-甲氧基吡啶-4-甲醛,5-Hydroxy-2-methoxy-pyridine-4-carbaldehyde)

快速询单

结构式：

5-羟基-2-甲氧基吡啶-4-甲醛MOL文件

CAS号：

867267-28-5

中文名称：

5-羟基-2-甲氧基吡啶-4-甲醛

英文名称：

5-Hydroxy-2-methoxy-pyridine-4-carbaldehyde

分子式：

C₇H₇NO₃

分子量：

153.135381937027

5-羟基-2-甲氧基吡啶-4-甲醛(867267-28-5)名称与标识符

名称

英文别名：

5-hydroxy-2-methoxy-4-Pyridinecarboxaldehyde;5-hydroxy-2-methoxypyridine-4-carbaldehyde;5-Hydroxy-2-methoxy-4-pyridinecarboxaldehyde (ACI);5-Hydroxy-2-methoxyisonicotinaldehyde;5-Hydroxy-2-methoxypyridine-4-carboxaldehyde;AB69287;867267-28-5;BS-50775;MFCD13189872;SCHEMBL15065382;CS-0119822;5-HYDROXY-2-METHOXY-PYRIDINE-4-CARBALDEHYDE;GRJJLRLFOQLVKR-UHFFFAOYSA-N;

标识符

MDL：

MFCD13189872

InChIKey：

GRJJLRLFOQLVKR-UHFFFAOYSA-N

Inchi：

1S/C7H7NO3/c1-11-7-2-5(4-9)6(10)3-8-7/h2-4,10H,1H3

SMILES：

O=CC1C(O)=CN=C(OC)C=1

5-羟基-2-甲氧基吡啶-4-甲醛(867267-28-5)物化性质

计算特性

精确分子量 : 153.042593085g/mol
氢键供体数量 : 1
氢键受体数量 : 4
可旋转化学键数量 : 2
同位素质量 : 153.042593085g/mol
重原子数量 : 11
复杂度 : 140
同位素原子数量 : 0
确定原子立构中心数量 : 0
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） : 0.8
拓扑分子极性表面积 : 59.4Å²

5-羟基-2-甲氧基吡啶-4-甲醛(867267-28-5)推荐厂家更多厂家(4)

公司名称	手机号/电话	联系人	QQ	询单
上海楷森生物科技有限公司	17558870519 175-58870519	赵经理		询单
上海腾准生物科技有限公司	19821570922 021-34053661	张经理	3003871136	询单
上海瀚思化工有限公司	18939883912 021-34536277	顾经理	3003949364	询单
上海绩祥生物科技有限公司	18605105771	李经理	1799924424	询单

5-羟基-2-甲氧基吡啶-4-甲醛(867267-28-5)合成路线

合成路线：1 步

867267-27-4

_95%

867267-28-5

反应条件：

1.1 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran , Water ; 3 h, 50 °C; 50 °C → rt
1.2 Reagents: Potassium carbonate Solvents: Water ; neutralized, rt

参考文献：

Solvent-dependent oxidations of 5- and 6-azaindoles to trioxopyrrolopyridines and functionalised azaindoles

Mahiout, Zahia; et al, Organic & Biomolecular Chemistry, 2008, 6(8), 1364-1376

合成路线：1 步

867267-27-4

_95%

867267-28-5

反应条件：

1.1 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran , Water ; 3 h, 50 °C

参考文献：

A regioselective route to 5- and 6-azaindoles

Lomberget, Thierry; et al, Synlett, 2005, (13), 2080-2082

合成路线：1 步

2332835-98-8

_87%

867267-28-5

反应条件：

1.1 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran ; 3 h, 40 °C; cooled
1.2 Reagents: Potassium carbonate Solvents: Water ; pH 7

参考文献：

3,5-Dialkoxypyridine analogues of bedaquiline are potent antituberculosis agents with minimal inhibition of the hERG channel

Sutherland, Hamish S.; et al, Bioorganic & Medicinal Chemistry, 2019, 27(7), 1292-1307

合成路线：1 步

2332835-98-8

_64%

867267-28-5

反应条件：

1.1 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran , Water ; 3 h, 40 °C
1.2 Reagents: Sodium bicarbonate Solvents: Water ; pH 7

参考文献：

Synthetic studies to help elucidate the metabolism of the preclinical candidate TBAJ-876-a less toxic and more potent analogue of bedaquiline

Choi, Peter J. ; et al, Molecules, 2020, 25(6),

合成路线：2 步

2332835-53-5

2591-86-8

867267-28-5

反应条件：

1.1 Reagents: Lithium diisopropylamide Solvents: Tetrahydrofuran ; -40 °C; 5 min, -40 °C; -40 °C → 0 °C; 3 h, 0 °C; 0 °C → -40 °C
1.2 -40 °C; 1 h, rt
2.1 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran , Water ; 3 h, 40 °C
2.2 Reagents: Sodium bicarbonate Solvents: Water ; pH 7

参考文献：

Synthetic studies to help elucidate the metabolism of the preclinical candidate TBAJ-876-a less toxic and more potent analogue of bedaquiline

Choi, Peter J. ; et al, Molecules, 2020, 25(6),

合成路线：2 步

2332835-53-5

2591-86-8

867267-28-5

反应条件：

1.1 Reagents: Lithium diisopropylamide Solvents: Tetrahydrofuran ; -40 °C → 0 °C; 3 h, 0 °C; 0 °C → -40 °C
1.2 -40 °C; 1 h, rt
1.3 Reagents: Acetic acid ; rt
2.1 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran ; 3 h, 40 °C; cooled
2.2 Reagents: Potassium carbonate Solvents: Water ; pH 7

参考文献：

3,5-Dialkoxypyridine analogues of bedaquiline are potent antituberculosis agents with minimal inhibition of the hERG channel

Sutherland, Hamish S.; et al, Bioorganic & Medicinal Chemistry, 2019, 27(7), 1292-1307

合成路线：2 步

431942-25-5

2591-86-8

867267-28-5

反应条件：

1.1 Reagents: Diisopropylamine , Methyllithium Solvents: Tetrahydrofuran ; -40 °C; -40 °C → 0 °C; 3 h, 0 °C; 0 °C → -40 °C
1.2 2 h, -40 °C
1.3 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran , Water ; -40 °C → rt
1.4 Reagents: Potassium carbonate Solvents: Ethyl acetate , Water ; pH 8 - 9
2.1 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran , Water ; 30 min, 50 °C; 50 °C → rt
2.2 Solvents: Water ; pH 7 - 8

参考文献：

Discovery of GBT440, an Orally Bioavailable R-State Stabilizer of Sickle Cell Hemoglobin

Metcalf, Brian; et al, ACS Medicinal Chemistry Letters, 2017, 8(3), 321-326

合成路线：2 步

431942-25-5

2591-86-8

867267-28-5

反应条件：

1.1 Catalysts: Diisopropylamine Solvents: Tetrahydrofuran ; rt → -40 °C
1.2 Reagents: Methyllithium Solvents: Diethyl ether ; -40 °C → 0 °C; 3 h, 0 °C; 0 °C → -40 °C
1.3 2 h, -40 °C
1.4 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran , Water ; -40 °C → 20 °C
1.5 Reagents: Potassium carbonate ; pH 8 - 9, 20 °C
2.1 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran , Water ; 3 h, 50 °C; 50 °C → rt
2.2 Reagents: Potassium carbonate Solvents: Water ; neutralized, rt

参考文献：

Solvent-dependent oxidations of 5- and 6-azaindoles to trioxopyrrolopyridines and functionalised azaindoles

Mahiout, Zahia; et al, Organic & Biomolecular Chemistry, 2008, 6(8), 1364-1376

合成路线：3 步

51834-97-0

13057-17-5

867267-28-5

反应条件：

1.1 Reagents: Potassium carbonate Solvents: Dimethylformamide ; 1 h, rt
2.1 Reagents: Diisopropylamine , Methyllithium Solvents: Tetrahydrofuran ; -40 °C; -40 °C → 0 °C; 3 h, 0 °C; 0 °C → -40 °C
2.2 2 h, -40 °C
2.3 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran , Water ; -40 °C → rt
2.4 Reagents: Potassium carbonate Solvents: Ethyl acetate , Water ; pH 8 - 9
3.1 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran , Water ; 30 min, 50 °C; 50 °C → rt
3.2 Solvents: Water ; pH 7 - 8

参考文献：

Discovery of GBT440, an Orally Bioavailable R-State Stabilizer of Sickle Cell Hemoglobin

Metcalf, Brian; et al, ACS Medicinal Chemistry Letters, 2017, 8(3), 321-326

合成路线：3 步

51834-97-0

3188-13-4

867267-28-5

反应条件：

1.1 Reagents: Sodium hydride Solvents: Dimethylformamide ; 0 °C; 0 °C → rt; 1 h, rt
1.2 4 h, rt
2.1 Reagents: Lithium diisopropylamide Solvents: Tetrahydrofuran ; -40 °C; 5 min, -40 °C; -40 °C → 0 °C; 3 h, 0 °C; 0 °C → -40 °C
2.2 -40 °C; 1 h, rt
3.1 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran , Water ; 3 h, 40 °C
3.2 Reagents: Sodium bicarbonate Solvents: Water ; pH 7

参考文献：

Synthetic studies to help elucidate the metabolism of the preclinical candidate TBAJ-876-a less toxic and more potent analogue of bedaquiline

Choi, Peter J. ; et al, Molecules, 2020, 25(6),

合成路线：3 步

51834-97-0

3188-13-4

867267-28-5

反应条件：

1.1 Reagents: Sodium hydride Solvents: Ethanol ; 0 °C; 0 °C → rt; 1 h, rt
1.2 2 h, rt
2.1 Reagents: Lithium diisopropylamide Solvents: Tetrahydrofuran ; -40 °C → 0 °C; 3 h, 0 °C; 0 °C → -40 °C
2.2 -40 °C; 1 h, rt
2.3 Reagents: Acetic acid ; rt
3.1 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran ; 3 h, 40 °C; cooled
3.2 Reagents: Potassium carbonate Solvents: Water ; pH 7

参考文献：

3,5-Dialkoxypyridine analogues of bedaquiline are potent antituberculosis agents with minimal inhibition of the hERG channel

Sutherland, Hamish S.; et al, Bioorganic & Medicinal Chemistry, 2019, 27(7), 1292-1307

合成路线：4 步

13472-85-0

867267-28-5

反应条件：

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ; 30 min, -78 °C
1.2 Reagents: Trimethyl borate ; 2 h, -78 °C
1.3 Reagents: Peracetic acid ; -78 °C → 0 °C; 1 h, 0 °C
2.1 Reagents: Sodium hydride Solvents: Dimethylformamide ; 45 min, rt
2.2 3 h, rt
3.1 Catalysts: Diisopropylamine Solvents: Tetrahydrofuran ; rt → -40 °C
3.2 Reagents: Methyllithium Solvents: Diethyl ether ; -40 °C → 0 °C; 3 h, 0 °C; 0 °C → -40 °C
3.3 2 h, -40 °C
3.4 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran , Water ; -40 °C → 20 °C
3.5 Reagents: Potassium carbonate ; pH 8 - 9, 20 °C
4.1 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran , Water ; 3 h, 50 °C; 50 °C → rt
4.2 Reagents: Potassium carbonate Solvents: Water ; neutralized, rt

参考文献：

Solvent-dependent oxidations of 5- and 6-azaindoles to trioxopyrrolopyridines and functionalised azaindoles

Mahiout, Zahia; et al, Organic & Biomolecular Chemistry, 2008, 6(8), 1364-1376