825-54-7 (1-苯基环戊烯,(cyclopent-1-en-1-yl)benzene)

100-58-3

_100%

反应条件：

1.1 Solvents: Diethyl ether , Tetrahydrofuran ; 0 °C → rt; 30 min, rt; 2 h, reflux

参考文献：

Identification and Preclinical Evaluation of the Bicyclic Pyrimidine γ-Secretase Modulator BMS-932481

Boy, Kenneth M. ; et al, ACS Medicinal Chemistry Letters, 2019, 10(3), 312-317

合成路线：1 步

2371-92-8

_100%

反应条件：

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran

参考文献：

Regiospecific syn β-elimination of 2-arylalkyl p-toluenesulfonates via ortho-lithiation

Sakai, Makoto; et al, Memoirs of the Faculty of Science, 1994, 19(2), 139-44

合成路线：1 步

2371-93-9

_100%

反应条件：

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran

参考文献：

Regiospecific syn β-elimination of 2-arylalkyl p-toluenesulfonates via ortho-lithiation

Sakai, Makoto; et al, Memoirs of the Faculty of Science, 1994, 19(2), 139-44

合成路线：1 步

591-50-4

_99%

反应条件：

1.1 Catalysts: Di-μ-chlorobis[(1,2,5,6-η)-1,5-cyclooctadiene]diiridium , Bis(pinacolato)diborane ; 16 h, 60 °C
1.2 Reagents: Cesium carbonate Catalysts: Triphenylphosphine , Palladium diacetate Solvents: Tetrahydrofuran , Water ; 16 h, 50 °C

参考文献：

Functionalization of Unactivated Alkenes through Iridium-Catalyzed Borylation of Carbon-Hydrogen Bonds. Mechanism and Synthetic Applications

Olsson, Vilhelm J.; et al, Journal of Organic Chemistry, 2009, 74(20), 7715-7723

合成路线：1 步

108-86-1

_98%

反应条件：

1.1 Reagents: Magnesium Solvents: Diethyl ether ; rt → reflux; 30 min, reflux; reflux → 0 °C
1.2 0 °C; 1 h, 0 °C
1.3 Solvents: Water ; cooled
1.4 Reagents: Acetic acid Solvents: Water ; 1.5 h, reflux; reflux → rt
1.5 Reagents: Sodium hydroxide Solvents: Water ; neutralized, rt

参考文献：

Enantioselective Hydroazidation of Trisubstituted Non-Activated Alkenes

Meyer, Daniel; et al, Angewandte Chemie, 2017, 56(36), 10858-10861

合成路线：1 步

108-86-1

_93%

反应条件：

1.1 Reagents: Magnesium , Iodine Solvents: Diethyl ether
1.2 Solvents: Diethyl ether
1.3 Reagents: Hydrochloric acid Solvents: Water
1.4 Reagents: p-Toluenesulfonic acid Solvents: Benzene

参考文献：

Stereoselective synthesis of δ-lactones from 5-oxoalkanals via one-pot sequential acetalization, Tishchenko reaction, and lactonization by cooperative catalysis of samarium ion and mercaptan

Hsu, Jue-Liang; et al, Journal of Organic Chemistry, 2001, 66(25), 8573-8584

合成路线：1 步

108-86-1

_73%

参考文献：

Synthesis and pharmacological activity of 6-aryl-2-azabicyclo[4.2.1]nonanes

Mazzocchiu, Paul H.; et al, Journal of Medicinal Chemistry, 1982, 25(12), 1473-6

合成路线：1 步

10487-96-4

_96%

反应条件：

1.1 Reagents: p-Toluenesulfonic acid Solvents: Benzene ; 3 h, reflux

参考文献：

Synthesis of 1-phenyl-1,2-cyclohexadiene and 1-(2-bromocyclohex-2-en-1-yl)benzene and Wurtz-like condensation products in the reaction of 1-(2,3-dibromocyclohex-1-en-1-yl)benzene with zinc

Ceylan, Mustafa; et al, Journal of Chemical Research, 2002, (9), 416-419

合成路线：1 步

10487-96-4

_95%

反应条件：

1.1 Catalysts: p-Toluenesulfonic acid Solvents: Benzene ; 1 h, reflux

参考文献：

Mo2C As Pre-Catalyst for the C-H Allylic Oxygenation of Alkenes and Terpenoids in the Presence of H2O2

Kallitsakis, Michael G.; et al, Organics, 2022, 3(3), 173-186

合成路线：1 步

10487-96-4

_93%

反应条件：

1.1 Reagents: Acetic acid ; 1 h, 118 °C; 118 °C → rt
1.2 Reagents: Sodium hydroxide Solvents: Water ; neutralized

参考文献：

Enantioselective Photoredox Catalysis Enabled by Proton-Coupled Electron Transfer: Development of an Asymmetric Aza-Pinacol Cyclization

Rono, Lydia J.; et al, Journal of the American Chemical Society, 2013, 135(47), 17735-17738

合成路线：1 步

108-90-7

_96%

反应条件：

1.1 Catalysts: Bis(hexafluoroacetylacetonato)palladium , Tri-tert-butylphosphonium tetrafluoroborate Solvents: 1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone ; 10 min, rt
1.2 Reagents: Diisopropylethylamine ; 27 h, 120 °C

参考文献：

Selective arylation at the vinylic site of cyclic olefins

Wu, Xiaojin; et al, Chemical Communications (Cambridge, 2013, 49(42), 4794-4796

合成路线：1 步

825-76-3

_96%

反应条件：

1.1 Catalysts: Bis(1,5-cyclooctadiene)nickel , 1,3-Bis[2,6-bis(1-methylethyl)phenyl]-1,3-dihydro-2H-imidazol-2-ylidene Solvents: Pentane ; 1 h, rt

参考文献：

Highly active nickel catalysts for the isomerization of unactivated vinyl cyclopropanes to cyclopentenes

Zuo, Gang; et al, Angewandte Chemie, 2004, 43(17), 2277-2279

合成路线：1 步

825-76-3

反应条件：

1.1 Catalysts: Triphenylsilane , Stereoisomer of [1,3-bis[2,6-bis(1-methylethyl)phenyl]-1,3-dihydro-2H-imidazol-2… Solvents: Hexane ; 3 h, 80 °C
1.2 Reagents: Oxygen

参考文献：

Modular Ni(0)/Silane Catalytic System for the Isomerization of Alkenes

Kawamura, Kiana E.; et al, Organometallics, 2022, 41(4), 486-496

合成路线：1 步

825-76-3

反应条件：

1.1 Reagents: 2-Butanol, 2-methyl-, sodium salt (1:1) Catalysts: Bis(1,5-cyclooctadiene)nickel , Nickel, bis[1,3-bis[2,6-bis(1-methylethyl)phenyl]-1,3-dihydro-2H-imidazol-2-ylid… Solvents: Toluene ; 2 h, 80 °C

参考文献：

Olefin functionalization/isomerization enables stereoselective alkene synthesis

Liu, Chen-Fei; et al, Nature Catalysis, 2021, 4(8), 674-683

合成路线：1 步

17763-67-6

_95%

反应条件：

1.1 Reagents: Lithium carbonate (Li2CO3) Catalysts: 1,3-Bis(diphenylphosphino)propane , Bis(hexafluoroacetylacetonato)palladium Solvents: Veratrole ; 48 h, 120 °C

参考文献：

Achieving Vinylic Selectivity in Mizoroki-Heck Reaction of Cyclic Olefins

Wu, Xiaojin; et al, Chemistry - A European Journal, 2013, 19(19), 6014-6020

合成路线：1 步

17763-67-6

_94%

反应条件：

1.1 Reagents: Zinc Catalysts: Nickel acetate , 1,2-Bis(dicyclohexylphosphino)ethane Solvents: Dimethylacetamide ; 15 min, rt
1.2 24 h, 100 °C

参考文献：

Nickel-catalyzed Heck reaction of cycloalkenes using aryl sulfonates and pivalates

Zhou, Jianrong Steve; et al, Chemical Communications (Cambridge, 2021, 57(32), 3933-3936

合成路线：1 步

16664-58-7

_95%

反应条件：

1.1 Reagents: Perchloric acid Solvents: Dichloromethane

参考文献：

Tris(aryl)aminium hexachloroantimonate: convenient one-electron oxidations for chemical electron transfer with bicyclic azoalkanes and bicyclo[2.1.0]pentanes

Adam, Waldemar; et al, Tetrahedron Letters, 1994, 35(48), 9027-30

合成路线：1 步

16664-58-7

参考文献：

UV-laser photochemistry of azoalkanes: surprising effects of phenyl substitution on the lifetimes of 1,3-cyclopentanediyl and 1,4-cyclohexanediyl triplet diradicals

Adam, Waldemar; et al, Journal of the American Chemical Society, 1989, 111(2), 751-3

合成路线：1 步

66950-63-8

_92%

反应条件：

1.1 Reagents: Zinc Catalysts: Dibromo[1,2-di(methoxy-κO)ethane]nickel , (R,R)-Ph-BPE Solvents: Dimethylformamide ; 15 min, rt
1.2 48 h, 100 °C

参考文献：

Nickel-catalyzed Heck reaction of cycloalkenes with Inert C-O bonds of aryl carbonates and aryl sulfamates

Zeng, Xuqun; et al, Youji Huaxue, 2022, 42(9), 2981-2987

合成路线：1 步

2996-92-1

_91%

反应条件：

1.1 Reagents: Tetrabutylammonium fluoride Catalysts: Palladium diacetate , P,P-Bis(1,1-dimethylethyl)-N-[2,8,9-tris(2-methylpropyl)-1λ5-2,5,8,9-tetraaza-1-… ; 0.5 h, 80 °C

参考文献：

Advantageous Use of tBu2P-N=P(iBuNCH2CH2)3N in the Hiyama Coupling of Aryl Bromides and Chlorides

Raders, Steven M.; et al, Journal of Organic Chemistry, 2010, 75(5), 1744-1747

合成路线：1 步

960-16-7

_91%

反应条件：

1.1 Reagents: Cesium fluoride Catalysts: Tris(dibenzylideneacetone)dipalladium , 2,8,9-Tris(phenylmethyl)-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane Solvents: 1,4-Dioxane ; 30 min, rt; 40 h, 100 °C

参考文献：

Highly active palladium catalysts supported by bulky proazaphosphatrane ligands for Stille cross-coupling: Coupling of aryl and vinyl chlorides, room temperature coupling of aryl bromides, coupling of aryl triflates, and synthesis of sterically hindered biaryls

Su, Weiping; et al, Journal of the American Chemical Society, 2004, 126(50), 16433-16439

合成路线：1 步

2248281-38-9

_88%

反应条件：

1.1 Reagents: Tetrabutylammonium iodide Solvents: (Trifluoromethyl)benzene ; rt; 8 - 24 h, 25 °C

参考文献：

Photoinduced Metal-Free Decarboxylative Transformations: Rapid Access to Amines, Alkyl Halides, and Olefins

Luo, Jia-jing; et al, European Journal of Organic Chemistry, 2023, 26(14),

合成路线：1 步

98-80-6

_88%

反应条件：

1.1 Reagents: Tripotassium phosphate Catalysts: Tris(dibenzylideneacetone)dipalladium , [2-(Diphenylphosphino)phenyl]ferrocene Solvents: Toluene ; 24 h, 110 °C

参考文献：

An active ferrocenyl triarylphosphine for palladium-catalyzed Suzuki-Miyaura cross-coupling of aryl halides

Kwong, Fuk Yee; et al, Chemical Communications (Cambridge, 2004, (20), 2336-2337

合成路线：1 步

98-80-6

_88%

反应条件：

1.1 Reagents: Tripotassium phosphate Catalysts: Tris(dibenzylideneacetone)dipalladium , 2-[Bis(1,1-dimethylethyl)phosphino]-N,N-diethylbenzamide Solvents: Toluene ; 19 h, 100 °C

参考文献：

A simple and highly efficient P,O-type ligand for Suzuki-Miyaura cross-coupling of aryl halides

Kwong, Fuk Yee; et al, Chemical Communications (Cambridge, 2004, (17), 1922-1923

合成路线：1 步

98-80-6

_87%

反应条件：

1.1 Reagents: Potassium fluoride , 18-Crown-6 Catalysts: Palladium diacetate , 1H-Imidazolium, 1,3-bis(7,10-dicyclohexyl-9-phenanthrenyl)-4,5-dihydro-, chlorid… Solvents: Tetrahydrofuran ; 16 h, 50 °C

参考文献：

Palladium catalyzed Suzuki-Miyaura coupling with aryl chlorides using a bulky phenanthryl N-heterocyclic carbene ligand

Song, Chun; et al, Tetrahedron, 2005, 61(31), 7438-7446

合成路线：1 步

66021-70-3

_84%

反应条件：

1.1 Solvents: o-Xylene ; 24 h, 160 °C

参考文献：

Synthesis of 1-Pyrroline by Denitrogenative Ring Expansion of Cyclobutyl Azides under Thermal Conditions

Miki, Yuya; et al, Advanced Synthesis & Catalysis, 2021, 363(14), 3481-3484

合成路线：1 步

_81%

反应条件：

1.1 Catalysts: Tetrakis(triphenylphosphine)palladium Solvents: Tetrahydrofuran

参考文献：

Phenylation of alkenyl triflates: reaction with tetrabutylammonium difluorotriphenylstannate

Martinez, A. Garcia; et al, Synlett, 1994, (12), 1047-8

合成路线：1 步

_81%

反应条件：

1.1 Catalysts: Tetrakis(triphenylphosphine)palladium Solvents: Tetrahydrofuran

参考文献：

Reactions of Vinyl and Aryl Triflates with Hypervalent Tin Reagents

Garcia Martinez, Antonio; et al, Organometallics, 2001, 20(5), 1020-1023

合成路线：1 步

24388-23-6

_81%

反应条件：

参考文献：

Palladium catalyzed Suzuki-Miyaura coupling with aryl chlorides using a bulky phenanthryl N-heterocyclic carbene ligand

Song, Chun; et al, Tetrahedron, 2005, 61(31), 7438-7446

合成路线：1 步

3262-89-3

_74%