91-48-5 (α-苯基肉桂酸,α-Phenylcinnamic Acid)

124-38-9

_100%

反应条件：

1.1 Reagents: Diisobutylaluminum hydride Solvents: Heptane ; 24 h, 25 °C
1.2 Reagents: Hydrogen ion Solvents: Water

参考文献：

Syntheses using alkyne-derived alkenyl- and alkynylaluminum compounds

Zweifel, George; et al, Organic Reactions (Hoboken, 1984, 32,

合成路线：1 步

124-38-9

_99%

反应条件：

1.1 Reagents: Isopropanol , Manganese Catalysts: Bathocuproine , Dichloro[1,2-di(methoxy-κO)ethane]nickel Solvents: Dimethylformamide ; 36 h, 60 °C
1.2 Reagents: Hydrochloric acid Solvents: Water

参考文献：

Ni-Catalyzed Regioselective Hydrocarboxylation of Alkynes with CO2 by Using Simple Alcohols as Proton Sources

Wang, Xueqiang; et al, Journal of the American Chemical Society, 2015, 137(28), 8924-8927

合成路线：1 步

_99%

反应条件：

1.1 Reagents: 4,5-Bis(diphenylphosphino)-9,9-dimethyl-9H-xanthene-2,7-disulfonic acid Catalysts: Palladium diacetate Solvents: Water ; 5 min
1.2 24 h, 3 bar, 100 °C; 0 °C

参考文献：

Access to α,β-unsaturated carboxylic acids through water-soluble palladium catalyzed hydroxycarbonylation of alkynes using water as the solvent

Lv, Jinhe; et al, Catalysis Science & Technology, 2021, 11(14), 4708-4713

合成路线：1 步

_89%

反应条件：

1.1 Reagents: Formic acid Catalysts: Triphenylphosphine , Palladium diacetate , 1,4-Bis(diphenylphosphino)butane Solvents: 1,2-Dimethoxyethane

参考文献：

Palladium-catalyzed hydrocarboxylation of alkynes with formic acid

Zargarian, Davit; et al, Organometallics, 1993, 12(3), 712-24

合成路线：1 步

_40%

反应条件：

1.1 Reagents: Formic-13C acid Catalysts: Palladium diacetate , 1,1′-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis[1,1-diphenylphosphine] Solvents: Toluene ; 12 h, 80 °C

参考文献：

Efficient hydrocarboxylation of alkynes based on carbodiimide-regulated in situ CO generation from HCOOH: An alternative indirect utilization of CO2

Xia, Shu-Mei; et al, Chinese Journal of Catalysis, 2022, 43(7), 1642-1651

合成路线：1 步

64-18-6

_98%

反应条件：

1.1 Reagents: Dicyclohexylcarbodiimide Catalysts: Palladium diacetate , 1,1′-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis[1,1-diphenylphosphine] Solvents: Toluene ; 12 h, 80 °C

参考文献：

Efficient hydrocarboxylation of alkynes based on carbodiimide-regulated in situ CO generation from HCOOH: An alternative indirect utilization of CO2

Xia, Shu-Mei; et al, Chinese Journal of Catalysis, 2022, 43(7), 1642-1651

合成路线：1 步

64-18-6

_95%

反应条件：

1.1 Catalysts: 1,3-Bis(diphenylphosphino)propane , Tris(dibenzylideneacetone)dipalladium , [1,3-Bis[2,6-bis(1-methylethyl)phenyl]-1,3-dihydro-2H-imidazol-2-ylidene]chloroc… Solvents: Toluene ; 15 min, rt
1.2 Reagents: Acetic anhydride ; 36 h, 100 °C

参考文献：

The synergistic copper/ppm Pd-catalyzed hydrocarboxylation of alkynes with formic acid as a CO surrogate as well as a hydrogen source: an alternative indirect utilization of CO2

Xia, Shu-Mei; et al, Green Chemistry, 2021, 23(20), 8089-8095

合成路线：1 步

702694-09-5

_94%

反应条件：

1.1 Reagents: Sodium tert-butoxide Solvents: Dimethyl sulfoxide ; 120 min, rt
1.2 Reagents: Water

参考文献：

Elimination vs. substitution in the reaction of 3-stannyl esters and 3-stannyl nitriles with sodium tert-butoxide in DMSO

Chopa, Alicia B.; et al, ARKIVOC (Gainesville, 2003, (10), 382-389

合成路线：1 步

14447-41-7

_92%

反应条件：

1.1 Reagents: Methyl iodide , Calcium hydroxide Catalysts: Dicobalt octacarbonyl Solvents: Methanol , 1,4-Dioxane

参考文献：

Carbonylation of vinyl halides with carbonylcobalt

Miura, Masahiro; et al, Journal of the Chemical Society, 1989, (1), 73-6

合成路线：1 步

15022-93-2

_92%

反应条件：

1.1 Reagents: Methyl iodide , Calcium hydroxide Catalysts: Dicobalt octacarbonyl Solvents: Methanol , 1,4-Dioxane

参考文献：

Carbonylation of vinyl halides with carbonylcobalt

Miura, Masahiro; et al, Journal of the Chemical Society, 1989, (1), 73-6

合成路线：1 步

702694-11-9

_91%

反应条件：

1.1 Reagents: Sodium tert-butoxide Solvents: Dimethyl sulfoxide ; 5 min, rt
1.2 Reagents: Water

参考文献：

Elimination vs. substitution in the reaction of 3-stannyl esters and 3-stannyl nitriles with sodium tert-butoxide in DMSO

Chopa, Alicia B.; et al, ARKIVOC (Gainesville, 2003, (10), 382-389

合成路线：1 步

13463-40-6

_75%

反应条件：

1.1 Reagents: Potassium tert-butoxide Solvents: Tetrahydrofuran ; 25 °C; 45 min, 60 °C; 60 °C → 25 °C
1.2 Reagents: Acetic acid ; rt; 1 h, rt
1.3 Solvents: Dichloromethane ; 1 h, 25 °C
1.4 25 °C; 10 h, 25 °C
1.5 Reagents: Dichloromethane Solvents: Acetone ; 25 °C

参考文献：

Stereoselective synthesis of α,β-unsaturated carboxylic acids from alkynes using the Fe(CO)5/t-BuOK/AcOH/CH2Cl2 reagent system

Beesu, Mallesh; et al, Journal of Organometallic Chemistry, 2012, 705, 30-33

合成路线：1 步

886-38-4

_72%

反应条件：

1.1 Reagents: Water Catalysts: Cupric acetate Solvents: Toluene ; 2 - 18 h, 110 °C
1.2 Reagents: Water

参考文献：

Click amidations, esterifications and one-pot reactions catalyzed by Cu salts and multimetal-organic frameworks (M-MOFs)

Greco, Rossella; et al, Molecular Catalysis, 2022, 522,

合成路线：1 步

886-38-4

反应条件：

1.1 Reagents: Bromobenzene , Cesium carbonate , Water Catalysts: Tri-m-tolylphosphine , Di-μ-chlorobis[(1,2,5,6-η)-1,5-cyclooctadiene]dirhodium Solvents: 1,2-Dichloroethane ; 18 h, 130 °C

参考文献：

Strain-Release-Driven Phosphine and Rhodium Catalysis: Facile Synthesis of Unsymmetrical Tetrasubstituted Alkenes

Zhang, Jing; et al, ACS Catalysis, 2023, 13(15), 10425-10434

合成路线：1 步

94025-75-9

_70%

反应条件：

1.1 Reagents: Triethylamine Solvents: Ethanol

参考文献：

Quantitative aspects of radical addition. I. The addition of bromotrichloromethane to cis- and trans-stilbene

Cadogan, J. I. G.; et al, Journal of the Chemical Society, 1962, 4154, 4154-63

合成路线：1 步

15321-51-4

_60%

反应条件：

1.1 Reagents: Potassium tert-butoxide Solvents: Tetrahydrofuran ; 25 °C; 0.5 h, 25 °C; 25 °C → 60 °C; 0.5 h, 60 °C; 60 °C → 25 °C
1.2 Reagents: Acetic acid ; rt; 1 h, rt
1.3 Solvents: Dichloromethane ; 1 h, 25 °C
1.4 25 °C; 10 h, 25 °C
1.5 Reagents: Dichloromethane Solvents: Acetone ; 25 °C

参考文献：

Stereoselective synthesis of α,β-unsaturated carboxylic acids from alkynes using the Fe(CO)5/t-BuOK/AcOH/CH2Cl2 reagent system

Beesu, Mallesh; et al, Journal of Organometallic Chemistry, 2012, 705, 30-33

合成路线：1 步

103-82-2

_58%

反应条件：

1.1 Reagents: Pyridine Solvents: Acetic anhydride ; 5 h, reflux
1.2 Reagents: Hydrochloric acid Solvents: Water ; overnight, acidified, rt

参考文献：

Synthesis of combretastatin analogs: evaluation of in vitro anticancer activity and molecular docking studies

Kumar, Sunil; et al, Medicinal Chemistry Research, 2012, 21(11), 3720-3729

合成路线：1 步

103-82-2

_26%

反应条件：

1.1 Reagents: Triethylamine Solvents: Acetic anhydride ; 24 h, heated
1.2 Reagents: Hydrochloric acid Solvents: Water ; rt

参考文献：

C2-Symmetric Cinchona Alkaloid Derivatives: Versatile Catalysts for the Enantioselective C-C Bond Forming Conjugate Addition of Nucleophiles to Simple α,β-Unsaturated Acyl Pyrazoles

Curran, Simon P.; et al, ChemistrySelect, 2020, 5(48), 15190-15194

合成路线：1 步

103-82-2

反应条件：

1.1 Reagents: Acetic anhydride , Triethylamine ; 24 h, 110 °C

参考文献：

Synthesis of alpha-pyrones and chromen-2-ones by transition-metal catalyzed annulations of sulfoxonium and iodonium ylides with cis-stilbene acids

John, Stephy Elza; et al, New Journal of Chemistry, 2022, 46(41), 19722-19730

合成路线：1 步

53558-55-7

_54%

反应条件：

1.1 Reagents: Chlorotrimethylsilane Solvents: Tetrahydrofuran

参考文献：

New Convenient One-Pot Methods of Conversion of Alkynes to Cyclobutenediones or α,β-Unsaturated Carboxylic Acids Using Novel Reactive Iron Carbonyl Reagents

Periasamy, Mariappan; et al, Journal of Organic Chemistry, 1998, 63(15), 4930-4935

合成路线：1 步

38654-91-0

_53%

反应条件：

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran , Hexane
1.2 Solvents: Tetrahydrofuran
1.3 Reagents: Water

参考文献：

A simple and efficient route to 2-alkyl-2-alkenoic acids and 2-phenyl-2-alkenoic acids by the Horner synthesis. Application to the stereoselective synthesis of the pheromone manicone

Coutrot, Philippe; et al, Synthesis, 1986, (9), 790-2

合成路线：1 步

558-13-4

103-30-0

_36%

反应条件：

1.1 Reagents: Dimethyl sulfoxide Catalysts: Cobalt iodide (CoI2) , Eosin ; 6 h, 100 °C

参考文献：

Carboxylation of styrenes with CBr4 and DMSO via cooperative photoredox and cobalt catalysis

Song, Cai-xia; et al, RSC Advances, 2017, 7(19), 11233-11243

合成路线：1 步

1370587-84-0

_32%

反应条件：

1.1 Reagents: Hydrochloric acid Solvents: Acetic acid , Water ; 48 h, 100 °C; 100 °C → rt
1.2 Reagents: Sodium bicarbonate Solvents: Water ; rt
1.3 Reagents: Hydrochloric acid Solvents: Water ; acidified, rt

参考文献：

Alkyne and Reversible Nitrile Activation: N,N'-Diamidocarbene-Facilitated Synthesis of Cyclopropenes, Cyclopropenones, and Azirines

Moerdyk, Jonathan P.; et al, Journal of the American Chemical Society, 2012, 134(14), 6116-6119

合成路线：1 步

645-49-8

558-13-4

_15%