94-62-2

_72%

反應條件：

1.1 Reagents: Dicyclohexylcarbodiimide Catalysts: 4-(Dimethylamino)pyridine

參考文獻：

Addition of carbon nucleophiles to aldehyde tosylhydrazones of aromatic and heteroaromatic-compounds: total synthesis of piperine and its analogs

Chandrasekhar, S.; Reddy, M. Venkat; Reddy, K. Srinivasa; Ramarao, C., Tetrahedron Letters, 2000, 41(15), 2667-2670

合成路線(xiàn)：1 步

_71%

反應條件：

1.1 Reagents: Dicyclohexylcarbodiimide Catalysts: 4-(Dimethylamino)pyridine Solvents: Dichloromethane ; rt

參考文獻：

Synthesis of (E,E)-Dienones and (E,E)-Dienals via Palladium-Catalyzed γ,δ-Dehydrogenation of Enones and Enals

Pan, Gao-Fei; Zhang, Xing-Long; Zhu, Xue-Qing; Guo, Rui-Li; Wang, Yong-Qiang, iScience, 2019, 20, 229-236

合成路線(xiàn)：1 步

736947-76-5

_82%

反應條件：

1.1 Reagents: Potassium hydroxide , Alumina Solvents: Dichloromethane , Dibromodifluoromethane ; 1 h, rt

參考文獻：

Stereoselective synthesis of naturally occurring unsaturated amide alkaloids by a modified Ramberg-Baecklund reaction

Li, Yang; Zhang, Yu; Huang, Zhi; Cao, Xiaoping; Gao, Kun, Canadian Journal of Chemistry, 2004, 82(5), 622-630

合成路線(xiàn)：1 步

675-20-7

_67%

反應條件：

1.1 Reagents: Oxalyl chloride Solvents: Dichloromethane ; 0 °C; 0 °C → rt; 4 h, rt
1.2 Solvents: Toluene ; rt; rt → reflux; 16 h, reflux

參考文獻：

Environmentally Benign Transamidation Protocol for Weakly Nucleophilic Aromatic Amines with N-Acyl-2-piperidinones: Catalyst-, Additive-, Base- and Solvent-Free Condition

Rajan, Ida Angel Priya Samuel; Subramani, Muthuraman; Pushparathinam, Gopinath; Rajendran, Saravanakumar, Asian Journal of Organic Chemistry, 2022, 11(9),

合成路線(xiàn)：1 步

203378-07-8

_48%

反應條件：

1.1 Reagents: Trifluoromethanesulfonic anhydride , 2-Iodopyridine Solvents: Dichloromethane ; 15 min, -20 °C
1.2 Reagents: Triethylamine , Benzeneseleninic acid , Dess-Martin periodinane Solvents: Dichloromethane ; 2 h, rt; 5 min, -20 °C; 5 - 60 min, -20 °C → 25 °C
1.3 Reagents: Sodium carbonate Solvents: Water ; 25 °C

參考文獻：

Chemoselective α,β-Dehydrogenation of Saturated Amides

Teskey, Christopher J.; Adler, Pauline; Goncalves, Carlos R.; Maulide, Nuno, Angewandte Chemie, 2019, 58(2), 447-451

合成路線(xiàn)：1 步

_95%

反應條件：

1.1 Reagents: Thionyl chloride Solvents: Dichloromethane

參考文獻：

A Short, Efficient, and Stereoselective Synthesis of Piperine and its Analogues

Bauer, Adriano; Nam, Jun-Hyun; Maulide, Nuno, Synlett, 2019, 30(4), 413-416

合成路線(xiàn)：1 步

_90%

反應條件：

1.1 Solvents: Tetrahydrofuran

參考文獻：

Three-component synthesis of (E)-α,β-unsaturated amides of the piperine family

Schobert, Rainer; Siegfried, Sven; Gordon, Gary J., Journal of the Chemical Society, 2001, (19), 2393-2397

合成路線(xiàn)：1 步

736947-76-5

_82%

反應條件：

1.1 Reagents: Potassium hydroxide , Alumina Solvents: Dichloromethane , Dibromodifluoromethane

參考文獻：

Stereoselective synthesis of piperamide alkaloids by modified Ramberg-Baecklund reaction

Li, Yang; Zhang, Yu; Wang, Xiao Long; Huang, Zhi; Cao, Xiao Ping, Chinese Chemical Letters, 2004, 15(6), 631-634

合成路線(xiàn)：1 步

_71%

反應條件：

1.1 Reagents: Dicyclohexylcarbodiimide Catalysts: 4-(Dimethylamino)pyridine Solvents: Dichloromethane ; rt; 18 h, rt

參考文獻：

Method for synthesizing piperine from 5-(1,2-methylenedioxyphenyl)-2-pentenal by oxidation and condensation

, China, , ,

合成路線(xiàn)：1 步

_93%

反應條件：

1.1 Reagents: Diisopropylethylamine , 1-[Bis(dimethylamino)methylene]-1H-benzotriazolium hexafluorophosphate(1-) 3-oxi… Solvents: Dimethylformamide ; 8 h, rt

參考文獻：

The development of novel cytochrome P450 2J2 (CYP2J2) inhibitor and the underlying interaction between inhibitor and CYP2J2

Tian, Xiangge; Zhou, Meirong; Ning, Jing; Deng, Xiaopeng; Feng, Lei; et al, Journal of Enzyme Inhibition and Medicinal Chemistry, 2021, 36(1), 737-748

合成路線(xiàn)：1 步

1802004-79-0

_83%

參考文獻：

A metal-free approach for transamidation of amides with amines in aqueous media

Srinivas, Mahesuni; Hudwekar, Abhinandan D.; Venkateswarlu, Vunnam; Reddy, G. Lakshma; Kumar, K. A. Aravinda; et al, Tetrahedron Letters, 2015, 56(33), 4775-4779

合成路線(xiàn)：1 步

_72%

反應條件：

1.1 Reagents: 1,1-Dimethylethyl 1-(1,1-dimethylethoxy)-2(1H)-isoquinolinecarboxylate Solvents: Dichloromethane ; 30 min, rt
1.2 24 h, rt

參考文獻：

Carboxamidation of carboxylic acids with 1-tert-butoxy-2-tert-butoxycarbonyl-1,2-dihydroisoquinoline (BBDI) without bases

Saito, Yukako; Ouchi, Hidekazu; Takahata, Hiroki, Tetrahedron, 2008, 64(49), 11129-11135

合成路線(xiàn)：1 步

38489-76-8

10043-37-5

_51%

反應條件：

1.1 Reagents: Triethylamine , N-Bromosuccinimide , Lithium chloride Catalysts: Triphenylantimony , Palladium diacetate , 1-Butanaminium, N,N,N-tributyl-, 2,2,2-trifluoroacetate (1:1) Solvents: Dichloroethane

參考文獻：

Catalytic Hunsdiecker reaction and one-pot catalytic Hunsdiecker-Heck strategy: synthesis of α,β-unsaturated aromatic halides, α-(dihalomethyl)benzenemethanols, 5-aryl-2,4-pentadienoic acids, dienoates and dienamides

Naskar, Dinabandhu; Roy, Sujit, Tetrahedron, 2000, 56(10), 1369-1377

合成路線(xiàn)：1 步

58095-77-5

1796-25-4

_94%

反應條件：

1.1 Reagents: Benzenemethanamine, 4-ethenyl-N,N-diethyl-, polymer with 1,1′-[1,4-butanediylbis… Solvents: 1-Propanol ; 24 h, 80 °C

參考文獻：

Chromatography-Free Wittig Reactions using a Bifunctional Polymeric Reagent

Leung, Peter Shu-Wai; Teng, Yan; Toy, Patrick H., Organic Letters, 2010, 12(21), 4996-4999

合成路線(xiàn)：1 步

_86%

反應條件：

1.1 Reagents: Sodium methoxide Solvents: Methanol ; 20 h, reflux

參考文獻：

Method for synthesis of piperine

, China, , ,

合成路線(xiàn)：1 步

_81%

反應條件：

1.1 Reagents: 2,4-Dichloro-6-methoxy-1,3,5-triazine Catalysts: Dabco Solvents: Ethyl acetate ; 30 min, rt
1.2 Reagents: Diisopropylethylamine Catalysts: 4-(Dimethylamino)pyridine Solvents: Ethyl acetate ; 30 min, rt; 1 h, rt

參考文獻：

Catalytic and Sustainable Amide Bond Formation using a DABCO/Dichlorotriazine System

Adler, Pauline ; Gras, Marion ; Smietana, Michael, ChemCatChem, 2023, 15(10),

合成路線(xiàn)：1 步

120-57-0

50838-22-7

_75%

反應條件：

1.1 Reagents: Sodium hydroxide Solvents: Dimethyl sulfoxide , Water ; 30 min, rt
1.2 6 - 8 h, rt
1.3 Reagents: Hydrochloric acid Solvents: Water ; rt

參考文獻：

Identification and optimization of piperine analogues as neuroprotective agents for the treatment of Parkinson's disease via the activation of Nrf2/keap1 pathway

Wang, Lun; Cai, Xiaoying; Shi, Mingsong; Xue, Linlin; Kuang, Shuang; et al, European Journal of Medicinal Chemistry, 2020, 199,

合成路線(xiàn)：1 步

_74%

反應條件：

1.1 Reagents: Thionyl chloride Solvents: Dichloromethane ; 10 min, cooled; rt; 2 h, rt
1.2 Solvents: Dichloromethane ; 2 - 2.5 h, 60 °C

參考文獻：

Synthesis, Antimicrobial, Antioxidant and Nematicidal Activity of (2E,4E)-5-(Benzo[d] [1,3]dioxol-5-yl)penta-2,4-dienamides

Wahab, Aneela; Sultana, Amina; Khan, Khalid Mohammed; Sherwani, Sikandar K.; Perveen, Zeba; et al, Journal of the Chemical Society of Pakistan, 2015, 37(5), 1008-1014

合成路線(xiàn)：1 步

203378-07-8

_69%

反應條件：

1.1 Reagents: Pivalic acid Catalysts: Cupric acetate , Palladium diacetate , 1,1′-[1,2-Ethanediylbis(sulfinyl)]bis[benzene] Solvents: Acetonitrile ; 24 h, 100 °C

參考文獻：

Synthesis of conjugated dienes via palladium-catalyzed aerobic dehydrogenation of unsaturated acids and amides

Keerthana, Meledath Sudhakaran; Jeganmohan, Masilamani, Chemical Communications (Cambridge, 2022, 58(63), 8814-8817

合成路線(xiàn)：1 步

57134-53-9

158504-70-2

_58%