884-35-5 (3,5-二甲氧基-4-羟基苯甲酸甲酯,methyl 4-hydroxy-3,5-dimethoxy-benzoate)

反应条件：

1.1 Reagents: Magnesium , Iodine Solvents: Diethyl ether ; 0 °C; 2 h, reflux
1.2 Solvents: Dichloromethane ; 1 h, 80 °C
1.3 Reagents: Sodium thiosulfate Solvents: Ethyl acetate , Water

参考文献：

A synthetic approach to chrysophaentin F

Vendeville, Jean-Baptiste; et al, Chemical Communications (Cambridge, 2019, 55(33), 4837-4840

合成路线：1 步

1916-07-0

_95%

反应条件：

1.1 Reagents: Boron trichloride

参考文献：

Boron trichloride as a selective demethylating agent for hindered ethers

Carvalho, Christopher F.; et al, Journal of the Chemical Society, 1984, (4), 227-9

合成路线：1 步

_100%

反应条件：

1.1 Catalysts: Sulfuric acid Solvents: Methanol ; 6 h, reflux

参考文献：

Synthesis and Antileukemic Activities of Piperlongumine and HDAC Inhibitor Hybrids against Acute Myeloid Leukemia Cells

Liao, Yi; et al, Journal of Medicinal Chemistry, 2016, 59(17), 7974-7990

合成路线：1 步

_96%

反应条件：

1.1 Reagents: Sulfuric acid Solvents: Methanol , Water ; rt → reflux; 3 h, reflux

参考文献：

Reactions of 2,2-diphenyl-1-picrylhydrazyl (DPPH) with two syringylic phenols or one aroxide derivative

Hristea, Elena N.; et al, European Journal of Organic Chemistry, 2009, (5), 626-634

合成路线：1 步

_100%

反应条件：

1.1 Reagents: 1,8-Bis(tetramethylguanidino)naphthalene Solvents: Dimethylformamide ; rt
1.2 Reagents: Formic acid Solvents: Water

参考文献：

Alkylation of carboxylic acids in a microfluidic device: kinetics parameters determination, Hammett reaction constant measurement and optimization of preparative experiment

Gholamipour-Shirazi, Azarmidokht; et al, International Electronic Conference on Synthetic Organic Chemistry, 2009, ,

合成路线：1 步

27065-65-2

_90%

反应条件：

1.1 Reagents: Nickel dichloride , Sodium borohydride Solvents: Methanol ; 5 - 10 min, 0 °C
1.2 Reagents: Methanol ; 20 min

参考文献：

NiCl2·6H2O/NaBH4 in methanol: a mild and efficient strategy for chemoselective deallylation/debenzylation of aryl ethers

Chouhan, Mangilal; et al, Tetrahedron Letters, 2013, 54(34), 4540-4543

合成路线：1 步

27065-65-2

参考文献：

Product class 8: ethers as protecting groups

Petursson, S., Science of Synthesis, 2008, 37, 847-892

合成路线：1 步

1147-85-9

_88%

反应条件：

1.1 Reagents: Nickel dichloride , Sodium borohydride Solvents: Methanol ; 5 - 10 min, 0 °C
1.2 Reagents: Methanol ; 20 min

参考文献：

NiCl2·6H2O/NaBH4 in methanol: a mild and efficient strategy for chemoselective deallylation/debenzylation of aryl ethers

Chouhan, Mangilal; et al, Tetrahedron Letters, 2013, 54(34), 4540-4543

合成路线：1 步

149-91-7

_74%

反应条件：

1.1 Reagents: Potassium carbonate Solvents: Dimethylformamide ; 1 h, reflux

参考文献：

Design and synthesis of a series of serine derivatives as small molecule inhibitors of the SARS coronavirus 3CL protease

Konno, Hiroyuki; et al, Bioorganic & Medicinal Chemistry, 2016, 24(6), 1241-1254

合成路线：1 步

_73%

反应条件：

1.1 Catalysts: 1,10-Phenanthroline Solvents: Methanol ; 36 h, 120 °C

参考文献：

Nickel-catalyzed para-selective carboxylation of phenols with CBr4/MeOH

Tu, Guangliang; et al, Organic Chemistry Frontiers, 2022, 9(14), 3876-3881

合成路线：1 步

118-41-2

_54%

反应条件：

1.1 Reagents: Boron trichloride Solvents: Dichloromethane ; -10 °C; 30 h, -10 °C → rt
1.2 Reagents: Sodium bicarbonate Solvents: Water ; rt

参考文献：

Synthesis of leptosin, a glycoside isolated from manuka honey

Aitken, Harry R. M.; et al, Tetrahedron Letters, 2013, 54(50), 6916-6919

合成路线：1 步

130774-07-1

参考文献：

Studies on the constituents of the bark of Kalopanax pictus Nakai

Sano, Kazuko; et al, Chemical & Pharmaceutical Bulletin, 1991, 39(4), 865-70

合成路线：1 步

134-96-3

反应条件：

1.1 Reagents: Oxygen Catalysts: Alumina , Gold ; 0.3 MPa, rt; 4 h, 140 °C

参考文献：

Gold-mediated selective transformation of lignin models to aromatic esters in the presence of molecular oxygen

Zhuang, Xuli; et al, Catalysis Today, 2017, 298, 190-196

合成路线：1 步

50597-60-9

反应条件：

1.1 Solvents: Diethyl ether ; 8 - 10 h, 70 - 80 °C

参考文献：

Phenolic acid derivatives as preservatives: synthesis, antioxidant, antimicrobial potential and their preservative effectiveness

Sigroha, Sumit; et al, International Journal of Pharmaceutical Sciences and Research, 2021, 12(10), 5526-5537

合成路线：1 步

91925-82-5

反应条件：

1.1 Reagents: Potassium carbonate
1.2 Reagents: Hydrogen Catalysts: Palladium

参考文献：

Synthesis and antioxidant activities of 3,5-dialkoxy-4-hydroxycinnamamides

Kang, Tae-Souk; et al, Bioorganic & Medicinal Chemistry Letters, 2008, 18(5), 1663-1667

合成路线：2 步

91925-82-5

参考文献：

Product class 8: ethers as protecting groups

Petursson, S., Science of Synthesis, 2008, 37, 847-892

合成路线：2 步

149-91-7

反应条件：

1.1 Catalysts: Sulfuric acid
1.2 Reagents: Dimethyl sulfate
2.1 Reagents: Zinc chloride Solvents: Propionic acid

参考文献：

Novel selective demethylation reaction-synthesis of 3,5- dimethoxy-4-hydroxybenzoate

Jing, Xiaobi; et al, Lanzhou Daxue Xuebao, 2001, 37(3), 78-79

合成路线：2 步

149-91-7

77-78-1

反应条件：

1.1 Reagents: Potassium carbonate Solvents: Acetone ; 4 h, reflux
2.1 Reagents: Aluminum chloride Solvents: Dichloromethane ; 4 h, rt

参考文献：

Synthesis of diverse analogues of Oenostacin and their antibacterial activities

Srivastava, Vandana; et al, Bioorganic & Medicinal Chemistry, 2007, 15(1), 518-525

合成路线：2 步

反应条件：

1.1 Reagents: Thionyl chloride Catalysts: Pyridine Solvents: Diethyl ether ; 2 - 4 h, 80 °C
2.1 Solvents: Diethyl ether ; 8 - 10 h, 70 - 80 °C

参考文献：

Phenolic acid derivatives as preservatives: synthesis, antioxidant, antimicrobial potential and their preservative effectiveness

Sigroha, Sumit; et al, International Journal of Pharmaceutical Sciences and Research, 2021, 12(10), 5526-5537

合成路线：3 步

100-44-7

99-24-1

参考文献：

Product class 8: ethers as protecting groups

Petursson, S., Science of Synthesis, 2008, 37, 847-892

合成路线：1 步

782452-40-8

_78%

反应条件：

1.1 Reagents: Ethylene glycol Solvents: Ethylene glycol ; 1 h, 120 °C

参考文献：

Simple deprotection of acetal type protecting groups under neutral conditions

Miyake, Hideyoshi; et al, Tetrahedron Letters, 2004, 45(39), 7213-7215

合成路线：1 步

1916-07-0

_64%