80904-75-2 (3-(hydroxymethyl)-2H-furan-5-one,4-(hydroxymethyl)-2,5-dihydrofuran-2-one)

反应条件：

1.1 Reagents: Acetyl chloride Solvents: Methanol ; overnight, rt

参考文献：

Application of the Palladium-Catalyzed Norbornene-Assisted Catellani Reaction Towards the Total Synthesis of (+)-Linoxepin and Isolinoxepin

Qureshi, Zafar; et al, European Journal of Organic Chemistry, 2014, 2014(19), 4053-4069

合成路线：1 步

77356-33-3

_99%

反应条件：

1.1 Reagents: Acetyl chloride Solvents: Methanol ; rt; 50 °C

参考文献：

Photochemical reactions of prop-2-enyl and prop-2-ynyl substituted 4-aminomethyl- and 4-oxymethyl-2(5H)-furanones

Fort, Diego A.; et al, Heterocycles, 2014, 88(2), 1079-1100

合成路线：1 步

77356-33-3

_99%

反应条件：

1.1 Reagents: Acetyl chloride Solvents: Methanol

参考文献：

Total Synthesis of (+)-Linoxepin by Utilizing the Catellani Reaction

Weinstabl, Harald; et al, Angewandte Chemie, 2013, 52(20), 5305-5308

合成路线：1 步

81189-55-1

_99%

反应条件：

1.1 Reagents: Acetyl chloride Solvents: Methanol ; overnight, rt

参考文献：

Application of the Palladium-Catalyzed Norbornene-Assisted Catellani Reaction Towards the Total Synthesis of (+)-Linoxepin and Isolinoxepin

Qureshi, Zafar; et al, European Journal of Organic Chemistry, 2014, 2014(19), 4053-4069

合成路线：1 步

81189-55-1

_78%

反应条件：

1.1 Reagents: Hydrochloric acid Solvents: Methanol ; 12 h, rt

参考文献：

Gas-phase fragmentation of γ-lactone derivatives by electrospray ionization tandem mass spectrometry

Crotti, Antonio E. M.; et al, Journal of Mass Spectrometry, 2009, 44(12), 1733-1741

合成路线：1 步

81189-55-1

_66%

反应条件：

1.1 Catalysts: p-Toluenesulfonic acid Solvents: Methanol , Tetrahydrofuran

参考文献：

From tetronic acid and furfural to C(4)-halogenated, vinylated, and formylated furan-2(5H)-ones and their 5-alkoxy derivatives

Lattmann, E.; et al, Synthesis, 1996, (1), 155-63

合成路线：1 步

1536873-76-3

_98%

反应条件：

1.1 Solvents: 1,4-Dioxane , Water ; 12 h, reflux

参考文献：

Unexpected Isomerization of Oxetane-Carboxylic Acids

Chalyk, Bohdan; et al, Organic Letters, 2022, 24(26), 4722-4728

合成路线：1 步

2503204-37-1

_98%

反应条件：

1.1 Solvents: 1,4-Dioxane , Water ; 12 h, 100 °C

参考文献：

Unexpected isomerization of oxetane-carboxylic acids

Chalyk, Bohdan; et al, ChemRxiv, 2022, 1, 1-8

合成路线：1 步

80661-17-2

_83%

反应条件：

1.1 Reagents: Sulfuric acid Solvents: Methanol , Water
1.2 Reagents: Sodium bicarbonate

参考文献：

Radical cyclizations onto 2(5H)-furanone and maleate electrophores. An approach to the spiro- and linear-fused γ-lactone ring systems found in the ginkgolides

Harrison, Timothy; et al, Tetrahedron, 1989, 45(16), 5247-62

合成路线：1 步

1200444-62-7

_70%

反应条件：

1.1 Reagents: Sulfuric acid Solvents: Methanol , Water ; 10 h, reflux
1.2 Reagents: Sodium bicarbonate

参考文献：

Synthesis of 4-(hydroxymethyl)-2(5h)-furanone and its effect on the biofilms of Pseudomonas aeruginosa

Wang, Yu-zhen; et al, Huaxue Shiji, 2010, 32(11), 970-972

合成路线：1 步

174655-88-0

_65%

反应条件：

1.1 Reagents: Diborane(4) Solvents: Tetrahydrofuran
1.2 Reagents: Acetic acid Solvents: Water

参考文献：

From tetronic acid and furfural to C(4)-halogenated, vinylated, and formylated furan-2(5H)-ones and their 5-alkoxy derivatives

Lattmann, E.; et al, Synthesis, 1996, (1), 155-63

合成路线：2 步

反应条件：

1.1 Solvents: tert-Butyl methyl ether ; reflux
2.1 Reagents: Acetyl chloride Solvents: Methanol ; rt; 50 °C

参考文献：

Photochemical reactions of prop-2-enyl and prop-2-ynyl substituted 4-aminomethyl- and 4-oxymethyl-2(5H)-furanones

Fort, Diego A.; et al, Heterocycles, 2014, 88(2), 1079-1100

合成路线：2 步

反应条件：

1.1 Solvents: tert-Butyl methyl ether ; overnight, 80 °C
2.1 Reagents: Acetyl chloride Solvents: Methanol ; overnight, rt

参考文献：

Application of the Palladium-Catalyzed Norbornene-Assisted Catellani Reaction Towards the Total Synthesis of (+)-Linoxepin and Isolinoxepin

Qureshi, Zafar; et al, European Journal of Organic Chemistry, 2014, 2014(19), 4053-4069

合成路线：2 步

反应条件：

1.1 Solvents: tert-Butyl methyl ether ; reflux
2.1 Reagents: Acetyl chloride Solvents: Methanol

参考文献：

Total Synthesis of (+)-Linoxepin by Utilizing the Catellani Reaction

Weinstabl, Harald; et al, Angewandte Chemie, 2013, 52(20), 5305-5308

合成路线：2 步

74181-34-3

反应条件：

1.1 Solvents: Benzene ; 12 h, reflux
2.1 Reagents: Sulfuric acid Solvents: Methanol , Water ; 10 h, reflux
2.2 Reagents: Sodium bicarbonate

参考文献：

Synthesis of 4-(hydroxymethyl)-2(5h)-furanone and its effect on the biofilms of Pseudomonas aeruginosa

Wang, Yu-zhen; et al, Huaxue Shiji, 2010, 32(11), 970-972

合成路线：2 步

1221819-52-8

反应条件：

1.1 Reagents: Sodium hydroxide Solvents: Methanol , Water ; overnight, rt
1.2 Reagents: Sodium bisulfate ; 10 min, pH 4 - 5, rt
2.1 Solvents: 1,4-Dioxane , Water ; 12 h, reflux

参考文献：

Unexpected Isomerization of Oxetane-Carboxylic Acids

Chalyk, Bohdan; et al, Organic Letters, 2022, 24(26), 4722-4728

合成路线：2 步

61934-55-2

127-08-2

反应条件：

1.1 Reagents: 18-Crown-6 Solvents: Acetonitrile ; 3 h, 60 °C
2.1 Reagents: Hydrochloric acid Solvents: Methanol ; 12 h, rt

参考文献：

Gas-phase fragmentation of γ-lactone derivatives by electrospray ionization tandem mass spectrometry

Crotti, Antonio E. M.; et al, Journal of Mass Spectrometry, 2009, 44(12), 1733-1741

合成路线：2 步

61934-55-2

127-08-2

反应条件：

1.1 Catalysts: 18-Crown-6 Solvents: Acetonitrile
2.1 Catalysts: p-Toluenesulfonic acid Solvents: Methanol , Tetrahydrofuran

参考文献：

From tetronic acid and furfural to C(4)-halogenated, vinylated, and formylated furan-2(5H)-ones and their 5-alkoxy derivatives

Lattmann, E.; et al, Synthesis, 1996, (1), 155-63

合成路线：2 步

61934-55-2

127-09-3

反应条件：

1.1 Reagents: 15-Crown-5 Solvents: Acetonitrile ; overnight, rt
2.1 Reagents: Acetyl chloride Solvents: Methanol ; overnight, rt

参考文献：

Application of the Palladium-Catalyzed Norbornene-Assisted Catellani Reaction Towards the Total Synthesis of (+)-Linoxepin and Isolinoxepin

Qureshi, Zafar; et al, European Journal of Organic Chemistry, 2014, 2014(19), 4053-4069

合成路线：2 步

867-13-0

反应条件：

1.1 Reagents: Sodium hydride Solvents: Tetrahydrofuran ; 0 °C; 1 h, 0 °C; 0 °C → rt; rt → 0 °C
1.2 0 °C; 12 h, rt
2.1 Reagents: Acetyl chloride Solvents: Methanol ; rt; 16 h, rt

参考文献：

Conformationally restricted pyrrolidines by intramolecular [2+2] photocycloaddition reactions

Fort, Diego A.; et al, Chemical Communications (Cambridge, 2013, 49(29), 2989-2991

合成路线：2 步

867-13-0

反应条件：

1.1 Reagents: Sodium hydride Solvents: Tetrahydrofuran
1.2 Solvents: Tetrahydrofuran
2.1 Reagents: Sulfuric acid Solvents: Methanol , Water
2.2 Reagents: Sodium bicarbonate

参考文献：

Radical cyclizations onto 2(5H)-furanone and maleate electrophores. An approach to the spiro- and linear-fused γ-lactone ring systems found in the ginkgolides

Harrison, Timothy; et al, Tetrahedron, 1989, 45(16), 5247-62

合成路线：2 步

867-13-0

反应条件：

1.1 Reagents: Sodium hydride Solvents: Tetrahydrofuran
2.1 Reagents: Sulfuric acid Solvents: Methanol , Water

参考文献：

Synthesis of 4-hydroxymethylfuran-2(5H)-one, a metabolite of the Celastraceae Siphonodon australe

Gadir, Suad A.; et al, Journal of Chemical Research, 1986, (6), 222-3

合成路线：2 步

97-65-4

反应条件：

1.1 Reagents: Sodium hydroxide , Bromine Solvents: Water
1.2 Reagents: Sulfuric acid
2.1 Reagents: Diborane(4) Solvents: Tetrahydrofuran
2.2 Reagents: Acetic acid Solvents: Water

参考文献：

From tetronic acid and furfural to C(4)-halogenated, vinylated, and formylated furan-2(5H)-ones and their 5-alkoxy derivatives

Lattmann, E.; et al, Synthesis, 1996, (1), 155-63

合成路线：3 步

10295-26-8

反应条件：

1.1 Reagents: Sodium hydroxide Solvents: Water ; overnight, rt
2.1 Reagents: 15-Crown-5 Solvents: Acetonitrile ; overnight, rt
3.1 Reagents: Acetyl chloride Solvents: Methanol ; overnight, rt

参考文献：

Application of the Palladium-Catalyzed Norbornene-Assisted Catellani Reaction Towards the Total Synthesis of (+)-Linoxepin and Isolinoxepin

Qureshi, Zafar; et al, European Journal of Organic Chemistry, 2014, 2014(19), 4053-4069

合成路线：3 步

96-26-4

108-24-7

反应条件：

1.1 Reagents: Pyridine ; overnight, rt
2.1 Solvents: tert-Butyl methyl ether ; overnight, 80 °C
3.1 Reagents: Acetyl chloride Solvents: Methanol ; overnight, rt

参考文献：

Application of the Palladium-Catalyzed Norbornene-Assisted Catellani Reaction Towards the Total Synthesis of (+)-Linoxepin and Isolinoxepin

Qureshi, Zafar; et al, European Journal of Organic Chemistry, 2014, 2014(19), 4053-4069

合成路线：3 步

89727-88-8

108-24-7