87751-69-7 ((±)-反式-1,3-二苯基烯丙基乙酸酯,Benzenemethanol, a-[(1E)-2-phenylethenyl]-, acetate)

_99%

反应条件：

1.1 Solvents: Pyridine ; 17 h, rt

参考文献：

D-Fructose Based Spiro-Fused Phosphinooxazoline Ligands: Palladium Complexes and Application in Catalysis

Imrich, Michael R.; et al, European Journal of Organic Chemistry, 2019, 2019(24), 3955-3963

合成路线：1 步

_94%

反应条件：

1.1 Reagents: Triethylamine Catalysts: 4-(Dimethylamino)pyridine Solvents: Dichloromethane ; 5 min, 0 °C
1.2 1 h, 0 °C; 0 °C → rt; 2 h, rt

参考文献：

Synthetic and mechanistic studies in enantioselective allylic substitutions catalysed by palladium complexes of a modular class of axially chiral quinazoline-containing ligands

Carroll, Anne-Marie; et al, Tetrahedron, 2020, 76(1),

合成路线：1 步

_93%

反应条件：

1.1 Reagents: Triethylamine Catalysts: 4-(Dimethylamino)pyridine Solvents: Dichloromethane ; rt
1.2 Reagents: Ammonium chloride Solvents: Water ; rt

参考文献：

Pd-Catalyzed Nazarov-Type Cyclization: Application in the Total Synthesis of β-Diasarone and Other Complex Cyclopentanoids

Singh, Bara; et al, Organic Letters, 2022, 24(4), 1043-1048

合成路线：1 步

_95%

反应条件：

1.1 Reagents: Triethylamine Solvents: Dichloromethane ; rt → 0 °C; 0 °C; 0 °C → rt; 4 h, rt

参考文献：

Carbamate-based P,O-ligands for asymmetric allylic alkylations

Palvoelgyi, Adam Mark; et al, Tetrahedron, 2020, 76(51),

合成路线：1 步

_87%

反应条件：

1.1 Reagents: Pyridine Catalysts: 4-(Dimethylamino)pyridine Solvents: Dichloromethane ; rt
1.2 Solvents: Water ; 15 min, rt

参考文献：

Pd/BIPHEPHOS is an Efficient Catalyst for the Pd-Catalyzed S-Allylation of Thiols with High n-Selectivity

Schlatzer, Thomas; et al, Advanced Synthesis & Catalysis, 2020, 362(2), 331-336

合成路线：1 步

反应条件：

1.1 Reagents: Pyridine Catalysts: 4-(Dimethylamino)pyridine Solvents: Dichloromethane ; 4 h, rt

参考文献：

Direct Reduction of Allylic Alcohols Using Isopropanol as Reductant

Sai, Masahiro, Advanced Synthesis & Catalysis, 2018, 360(18), 3482-3487

合成路线：1 步

141-78-6

_92%

反应条件：

1.1 Reagents: (SP-5-12)-(Pyridine)bis[tetrahydroborato(1-)-κH,κH′]zinc Solvents: Tetrahydrofuran , Ethyl acetate ; 12 h, reflux

参考文献：

Reductive acetylation of carbonyl compounds to acetates with pyridine zinc borohydride

Zeynizadeh, Behzad; et al, Bulletin of the Korean Chemical Society, 2008, 29(1), 76-80

合成路线：1 步

108-22-5

_90%

反应条件：

1.1 Catalysts: μ5-Oxotetrakis[μ-(2-propanolato)]tetrakis[μ3-(2-propanolato)]pentakis(2-propanol… Solvents: Toluene

参考文献：

Metal-Catalyzed Acyl Transfer Reactions of Enol Esters: Role of Y5(OiPr)13O and (thd)2Y(OiPr) as Transesterification Catalysts

Lin, Mei-Huey; et al, Organic Letters, 2000, 2(7), 997-1000

合成路线：1 步

_89%

参考文献：

Synthesis of chiral P,N-ligands and application of their Pd-complexes in asymmetric allylic alkylation

He, Wei; et al, Fenzi Cuihua, 2006, 20(2), 149-152

合成路线：2 步

反应条件：

1.1 Reagents: Sodium borohydride Solvents: Methanol ; 4 h, 0 °C
1.2 Reagents: Water
2.1 Reagents: Triethylamine Catalysts: 4-(Dimethylamino)pyridine Solvents: Dichloromethane ; rt → 0 °C
2.2 0 °C; 30 min, rt
2.3 Reagents: Ammonium chloride Solvents: Water ; rt

参考文献：

An Axially Chiral Styrene-Phosphine Ligand for Pd-Catalyzed Asymmetric N-Alkylation of Indoles

Chen, Zhen-Bang; et al, Journal of Organic Chemistry, 2023, 88(20), 14719-14727

合成路线：2 步

反应条件：

1.1 Reagents: Sodium borohydride Solvents: Methanol ; 0 °C; 6 h, rt
1.2 Solvents: Water ; rt
2.1 Reagents: Triethylamine Catalysts: 4-(Dimethylamino)pyridine Solvents: Diethyl ether ; 0 °C; 2 h, rt
2.2 Reagents: Sodium bicarbonate Solvents: Water ; rt

参考文献：

B(3,4,5-F3H2C6)3 Lewis acid-catalysed C3-allylation of indoles

Alotaibi, Nusaybah; et al, Dalton Transactions, 2023, 52(16), 5039-5043

合成路线：1 步

109603-92-1

37973-54-9

_84%

反应条件：

1.1 Reagents: Manganate(2-), tetrachloro-, dilithium, (T-4)- Solvents: Tetrahydrofuran ; 15 min, 0 °C; 30 min, 0 °C → rt
1.2 Catalysts: Chlorotrimethylsilane , Copper(1+), bis(acetonitrile)bis(triphenylphosphine)-, (T-4)-, tetrafluoroborate… Solvents: Tetrahydrofuran ; 20 min, 10 °C
1.3 Solvents: Tetrahydrofuran ; 15 - 30 min, rt; 1 - 2 h, rt

参考文献：

Copper-catalyzed substitution reactions of acylal with organomanganese reagents

Deshmukh, Madhukar B.; et al, Indian Journal of Chemistry, 2007, (6), 989-994

合成路线：1 步

3412-44-0

64-19-7

_80%

反应条件：

1.1 Solvents: Water

参考文献：

Selenium dioxide oxidations. III. Oxidation of olefins

Schaefer, John P.; et al, Journal of Organic Chemistry, 1968, 33(7), 2647-55

合成路线：1 步

7217-71-2

591-50-4

_73%

反应条件：

1.1 Reagents: Silver carbonate , Oxygen Catalysts: Palladium diacetate Solvents: Toluene ; rt; rt → reflux; 10 h, reflux

参考文献：

Ligand-free Pd-catalyzed highly selective arylation of allylic esters with retention of the traditional leaving group

Pan, Delin; et al, Angewandte Chemie, 2008, 47(25), 4729-4732

合成路线：1 步

_70%

反应条件：

1.1 Reagents: Sodium borohydride Solvents: Methanol ; 0 °C; 0 °C → rt; 1 h, rt
1.2 Reagents: Triethylamine , 4-(Dimethylamino)pyridine Solvents: Dichloromethane ; rt; rt → 0 °C
1.3 0 °C; 0 °C → rt; overnight, rt

参考文献：

Design, Synthesis, and Application of Chiral C2-Symmetric Spiroketal-Containing Ligands in Transition-Metal Catalysis

Argueelles, Alonso J.; et al, Angewandte Chemie, 2018, 57(19), 5325-5329

合成路线：1 步

反应条件：

1.1 Reagents: Sodium borohydride Solvents: Methanol ; 1 h
1.2 Reagents: Triethylamine Catalysts: 4-(Dimethylamino)pyridine Solvents: Dichloromethane ; 10 h

参考文献：

Inherently chiral 6,7-diphenyldibenzo[e,g][1,4]diazocine: enantioselective synthesis and application as a ligand platform

Luo, Yu; et al, CCS Chemistry, 2023, 5(4), 982-993

合成路线：1 步

_46%

反应条件：

1.1 Reagents: Sodium carbonate , Sodium iodide Catalysts: 1,3-Bis(diphenylphosphino)propane , Dicarbonylrhodium acetylacetonate Solvents: 1,4-Dioxane ; 20 h, 0.2 MPa, 150 °C

参考文献：

Rh-catalyzed alkoxycarbonylation of unactivated alkyl chlorides

Wang, Peng; et al, Chemical Science, 2022, 13(45), 13459-13465

合成路线：1 步

7217-71-2

98-80-6

_20%

反应条件：

1.1 Reagents: Silver acetate , Copper fluoride (CuF2) , Potassium bifluoride Catalysts: Palladium diacetate Solvents: Acetone ; 5 h, 85 °C

参考文献：

Control of Chemo-, Regio-, and Stereoselectivities in Ligand-Free Pd-Catalyzed Oxidative Heck Reactions of Arylboronic Acids or Alkenylboronate with Allyl Esters

Su, Yijin; et al, Organic Letters, 2009, 11(14), 2980-2983

合成路线：1 步

反应条件：

1.1 Solvents: Diethyl ether
1.2 Reagents: Pyridine Solvents: Pyridine

参考文献：

A New Guanidinylation Procedure for the Preparation of Functionalized Guanidines and Investigations Towards the Synthesis of Cyclic Guanidine Compounds

Ramsden, Philip Dean, 2003, , ,

合成路线：1 步

参考文献：

Silylium-Catalyzed Alkynylation and Etherification Reactions of Benzylic Acetates

Rubial, Belen ; et al, European Journal of Organic Chemistry, 2022, 2022(26),

合成路线：1 步

参考文献：

Transient [3,3] Cope rearrangement of 3,3-dicyano-1,5-dienes: computational analysis and 2-step synthesis of arylcycloheptenes

Fereyduni, Ehsan; et al, Chemical Science, 2018, 9(46), 8760-8764

合成路线：1 步

94-41-7

反应条件：

1.1 Reagents: Sodium borohydride
1.2 Reagents: Triethylamine

参考文献：

NAD(P)+-NAD(P)H models. 55. Transition metal catalyzed reduction of organic halides: high selectivity for reductive dehalogenation

Yasui, Shinro; et al, Journal of Organic Chemistry, 1985, 50(18), 3283-7

合成路线：2 步

104-55-2

100-58-3

反应条件：

1.1 Solvents: Diethyl ether ; overnight, rt
1.2 Reagents: Ammonium chloride Solvents: Water
2.1 Reagents: Triethylamine Solvents: Dichloromethane ; overnight, rt

参考文献：

New Insights into the Mechanism of Palladium-Catalyzed Allylic Amination

Watson, Iain D. G.; et al, Journal of the American Chemical Society, 2005, 127(49), 17516-17529

合成路线：2 步

100-58-3

反应条件：

1.1 20 min, 0 °C; 0 °C → rt; 18 h, rt
1.2 Reagents: Ammonium chloride Solvents: Water ; rt
2.1 Reagents: Triethylamine Solvents: Dichloromethane ; 10 min, 0 °C
2.2 10 min, 0 °C; 0 °C → rt; 2 d, rt

参考文献：

Reducing Diastereomorphous Bis(phosphane oxide) Atropisomers to One Atropisomerically Pure Diphosphane: A New Ligand and a Novel Ligand-Preparation Design

Sartorius, Frank; et al, Chemistry - A European Journal, 2017, 23(69), 17463-17468

合成路线：2 步

反应条件：

1.1 Catalysts: Sulfuric acid ; 0 °C → rt
2.1 Reagents: Manganate(2-), tetrachloro-, dilithium, (T-4)- Solvents: Tetrahydrofuran ; 15 min, 0 °C; 30 min, 0 °C → rt
2.2 Catalysts: Chlorotrimethylsilane , Copper(1+), bis(acetonitrile)bis(triphenylphosphine)-, (T-4)-, tetrafluoroborate… Solvents: Tetrahydrofuran ; 20 min, 10 °C
2.3 Solvents: Tetrahydrofuran ; 15 - 30 min, rt; 1 - 2 h, rt

参考文献：

Copper-catalyzed substitution reactions of acylal with organomanganese reagents

Deshmukh, Madhukar B.; et al, Indian Journal of Chemistry, 2007, (6), 989-994

合成路线：2 步

108-86-1

反应条件：

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran , Hexane ; -78 °C; 1 h, -78 °C
1.2 Solvents: Tetrahydrofuran ; 15 min, -78 °C; 30 min, rt
1.3 Reagents: Ammonium chloride Solvents: Water ; rt
2.1 Reagents: Triethylamine Catalysts: 4-(Dimethylamino)pyridine Solvents: Dichloromethane ; rt
2.2 Reagents: Ammonium chloride Solvents: Water ; rt

参考文献：

Pd-Catalyzed Nazarov-Type Cyclization: Application in the Total Synthesis of β-Diasarone and Other Complex Cyclopentanoids

Singh, Bara; et al, Organic Letters, 2022, 24(4), 1043-1048

合成路线：2 步

108-86-1

反应条件：

1.1 Solvents: Diethyl ether ; 45 min, reflux
1.2 overnight, rt
1.3 Reagents: Ammonium chloride Solvents: Water ; rt
2.1 Reagents: Triethylamine Solvents: Dichloromethane ; 0 °C
2.2 0 °C; overnight, rt

参考文献：

Unusual Selectivity of Unprotected Aziridines in Palladium-Catalyzed Allylic Amination Enables Facile Preparation of Branched Aziridines

Watson, Iain D. G.; et al, Journal of the American Chemical Society, 2004, 126(16), 5086-5087

合成路线：2 步

108-86-1

反应条件：

1.1 Solvents: Tetrahydrofuran
2.1 Reagents: Triethylamine Solvents: Dichloromethane

参考文献：

Synthesis of Chiral Thiophene-containing Ligands and their Development in the Asymmetric Transition Metal Catalysis

Lohmann, Jan Klaas, 2003, , ,

合成路线：3 步

98-86-2

100-52-7

反应条件：

1.1 Reagents: Sodium hydroxide Solvents: Ethanol , Water ; 0 °C; 5 min, 0 °C
1.2 0 °C; rt
2.1 Reagents: Sodium borohydride Solvents: Methanol ; 0 °C; 6 h, rt
2.2 Solvents: Water ; rt
3.1 Reagents: Triethylamine Catalysts: 4-(Dimethylamino)pyridine Solvents: Diethyl ether ; 0 °C; 2 h, rt
3.2 Reagents: Sodium bicarbonate Solvents: Water ; rt

参考文献：

B(3,4,5-F3H2C6)3 Lewis acid-catalysed C3-allylation of indoles

Alotaibi, Nusaybah; et al, Dalton Transactions, 2023, 52(16), 5039-5043

合成路线：3 步

98-86-2

100-52-7

反应条件：

1.1 Reagents: Sodium hydroxide Solvents: Ethanol , Water ; 0 °C; rt
2.1 Reagents: Sodium borohydride Solvents: Methanol ; 0 °C; 5 h, rt
2.2 Reagents: Hydrochloric acid Solvents: Water ; pH 7, rt
3.1 Reagents: Triethylamine Catalysts: 4-(Dimethylamino)pyridine Solvents: Dichloromethane ; 24 h, rt

参考文献：

Preparation and Application of Amino Phosphine Ligands Bearing Spiro[indane-1,2'-pyrrolidine] Backbone

Li, Shasha; et al, Journal of Organic Chemistry, 2019, 84(15), 9460-9473

合成路线：3 步

98-86-2

100-52-7