922-67-8 (丙炔酸甲酯,methyl prop-2-ynoate)

_85%

反应条件：

1.1 Reagents: Dicyclohexylcarbodiimide Catalysts: 4-(Dimethylamino)pyridine Solvents: Dichloromethane ; 1 h, 0 °C; 5 h, rt

参考文献：

Asymmetric synthesis of dihydrocarbazoles through a Friedel-Crafts alkylation/annulation sequential reaction of indoles

Hu, Linfeng; Cao, Weidi; Wang, Kaixuan; Liu, Xiaohua; Feng, Xiaoming, Chemical Communications (Cambridge, 2021, 57(97), 13138-13141

合成路线：1 步

_85%

反应条件：

1.1 Reagents: Trimethyl orthoformate Catalysts: Sulfuric acid Solvents: Dichloromethane ; 28 h, 40 °C

参考文献：

Environment-friendly preparation method of propiolic acid derivative

, China, , ,

合成路线：1 步

97914-78-8

36993-85-8

_82%

参考文献：

Addition of 4-ethoxyimidazoles to dimethyl acetylenedicarboxylate and transformation of the adducts to pyrimidin-5-yl acetates

Furuya, Shuichi; Omura, Kiyoshi; Furukawa, Yoshiyasu, Chemical & Pharmaceutical Bulletin, 1988, 36(5), 1669-75

合成路线：1 步

_80%

反应条件：

1.1 Reagents: Dicyclohexylcarbodiimide Catalysts: 4-(Dimethylamino)pyridine Solvents: Dichloromethane ; 30 min, 0 °C; rt

参考文献：

Palladium-Catalyzed Regio- and Stereoselective Coupling-Addition of Propiolates with Arylsulfonyl Hydrazides: A Pattern for Difunctionalization of Alkynes

Liu, Lixin; Sun, Kang; Su, Lebin; Dong, Jianyu; Cheng, Lei; et al, Organic Letters, 2018, 20(13), 4023-4027

合成路线：1 步

_75%

反应条件：

1.1 Reagents: Sulfuric acid ; 24 h, reflux

参考文献：

Approaches to the total synthesis of dl-vernolepin

Medwid, Effrey Brian, 1980, , ,

合成路线：1 步

_75%

反应条件：

1.1 Reagents: Sulfuric acid

参考文献：

Addition reactions of heterocyclic compounds. XL. Methyl propiolate with some quinolines, isoquinolines, and phenanthridines

Acheson, Richard M.; Verlander, M. S., Journal of the Chemical Society [Section] C: Organic, 1969, (17), 2311-15

合成路线：1 步

_63%

反应条件：

1.1 Reagents: Sulfuric acid Solvents: Methanol , Water

参考文献：

Some uses of organosilicon compounds in organic synthesis

Percival, Alan, 1977, , ,

合成路线：1 步

_60%

反应条件：

1.1 Reagents: Methanol , Boron trifluoride etherate Solvents: Methanol

参考文献：

The stereochemistry of addition of trialkylammonium and pyridinium tetrafluoroborate salts to activated acetylenes. Preparation of novel dienophiles for Diels-Alder reactions

Jung, Michael E.; Buszek, Keith R., Journal of the American Chemical Society, 1988, 110(12), 3965-9

合成路线：1 步

74-88-4

_58%

反应条件：

1.1 Reagents: Tetraethylammonium p-toluenesulfonate Solvents: Dimethylformamide

参考文献：

Esterification, etherification, and aldol condensation using cathodically generated organic olate anions

Fuchigami, Toshio; Awata, Takeshi; Nonaka, Tsutomu; Baizer, Manuel M., Bulletin of the Chemical Society of Japan, 1986, 59(9), 2873-9

合成路线：1 步

_56%

反应条件：

1.1 Reagents: Sulfuric acid Solvents: Methanol

参考文献：

Action of Grignard reagents on the esters of propiolic acid

Rhinesmith, Herbert S., Journal of Organic Chemistry, 1975, 40(12), 1773-6

合成路线：1 步

_50%

参考文献：

Complete kinetic analysis of thermal stereomutations among the eight 2,3-dideuterio-2-(methoxymethyl)spiro[cyclopropane-1,1'-indenes]

Baldwin, John E.; Black, Kersey A., Journal of the American Chemical Society, 1984, 106(4), 1029-40

合成路线：1 步

_46%

反应条件：

1.1 Reagents: Sulfuric acid ; 48 h, 25 °C

参考文献：

Studies on the 1-aza-1'-oxa-[3,3]-sigmatropic rearrangement: synthesis of ortho-(β-oxoalkyl)anilides and regiospecifically substituted indoles

Burgoyne, William Franklin Jr., 1981, , ,

合成路线：1 步

16754-74-8

_30%

参考文献：

Flash-vacuum pyrolysis of stabilized phosphorus ylides. Part 9. Preparation and pyrolysis of β,γ-dioxo ylides, β,β',γ,γ'-tetraoxo ylides and hexaoxo bis(ylides)

Aitken, R. Alan; Karodia, Nazira, Liebigs Annalen/Recueil, 1997, (4), 779-783

合成路线：1 步

61617-47-8

参考文献：

Synthesis of linear alkynes by rearrangement

Krueger, A., Science of Synthesis, 2008, 43, 469-554

合成路线：1 步

反应条件：

1.1 Reagents: Sulfuric acid Solvents: Water ; 1 h, reflux

参考文献：

Environmental impact analysis of surface printing and 3D inkjet printing applications using an imine based covalent organic framework: A life cycle assessment study

Espada, Juan J. ; Rodriguez, Rosalia; de la Pena, Alejandro; Ramos, Mar; Segura, Jose L. ; et al, Journal of Cleaner Production, 2023, 395,

合成路线：1 步

反应条件：

1.1 Reagents: Dicyclohexylcarbodiimide Catalysts: 4-(Dimethylamino)pyridine Solvents: Dichloromethane ; 0 °C; 1 - 12 h, 0 °C

参考文献：

Flash vacuum pyrolysis of 1-Aryl-1,2,3-triazole-4-carboxylate esters and -4-carboxamides

Habib, Osama M.; Mohamed, Asaad S.; Al-Awadi, Nouria A., Journal of Analytical and Applied Pyrolysis, 2023, 170,

合成路线：1 步

反应条件：

1.1 Catalysts: p-Toluenesulfonic acid Solvents: Toluene ; 18 h, reflux

参考文献：

Metal-free synthesis of N-vinyl sulfoximines via DABCO-participated Michael addition of terminal carbonyl alkynes with N-chlorosulfoximines

Tang, Yisong; Tang, Yaonan; Rui, zhu; Zheng, Shaojun; Cheng, Xiaofang; et al, Tetrahedron, 2022, 129,

合成路线：1 步

反应条件：

1.1 Reagents: Dicyclohexylcarbodiimide Solvents: Dichloromethane ; 0 °C; 2 h, 0 °C; 0 °C → 23 °C; 23 °C
1.2 Solvents: Ethyl acetate ; 1 h, 0 °C

参考文献：

One-Pot Synthesis of Chromone Fused-Pyrrolo[2,1-a]isoquinolines and Indolizino[8,7-b]indoles: Iodine Promoted Oxidative [2+2+1] Annulation of O-acetylphenoxyacrylates with Tetrahydroisoquinolines and Noreleagnines

Shang, Zhi-Hao; Zhang, Xiang-Jin; Li, Yi-Ming; Wu, Rui-Xue; Zhang, Hui-Ru; et al, Journal of Organic Chemistry, 2021, 86(21), 15733-15742

合成路线：1 步

反应条件：

1.1 Catalysts: p-Toluenesulfonic acid Solvents: Toluene ; 12 h, reflux

参考文献：

Nature-inspired remodeling of (aza)indoles to meta-aminoaryl nicotinates for late-stage conjugation of vitamin B3 to (hetero)arylamines

Varun, Begur Vasanthkumar ; Vaithegi, Kannan ; Yi, Sihyeong ; Park, Seung Bum, Nature Communications, 2020, 11(1),

合成路线：1 步