928-90-5 (5-己炔-1-醇,Hex-5-yn-1-ol)

_94%

反应条件：

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran , Hexane

参考文献：

Synthesis and Activity of Boron-containing compounds for Selective Tumour Therapy using Neutron Irradiation

Griesbach, Ulrich, 2002, , ,

合成路线：1 步

73448-13-2

_93%

反应条件：

1.1 Reagents: Hydrochloric acid Solvents: Methanol , Water ; 1 h, 23 °C
1.2 Reagents: Triethylamine ; neutralized

参考文献：

Regioselectivity Influences in Platinum-Catalyzed Intramolecular Alkyne O-H and N-H Additions

Costello, Jeff P.; Ferreira, Eric M., Organic Letters, 2019, 21(24), 9934-9939

合成路线：1 步

53293-00-8

_91%

反应条件：

1.1 Reagents: Lithium aluminum hydride Solvents: Diethyl ether ; 0 °C; 0 °C → rt; 3 h, rt; rt → 0 °C
1.2 Reagents: Sodium sulfate Solvents: Water ; 0 °C

参考文献：

synthesis and biological activity of 20-hete antagonists and agonists

, World Intellectual Property Organization, , ,

合成路线：1 步

_89%

反应条件：

1.1 Reagents: Lithium , Ammonia Catalysts: Ferric nitrate ; 5 h, -25 °C
1.2 Reagents: Ammonium chloride Solvents: 2-Methyltetrahydrofuran , Water ; -25 °C → 35 °C
1.3 Reagents: Chloroacetic acid ; pH 9.5

参考文献：

A process for preparing chlorinated alkynes from epoxy alcohols

, China, , ,

合成路线：1 步

17889-21-3

_89%

反应条件：

1.1 Reagents: Sulfuric acid , Water

参考文献：

Synthesis of some acetylenic alcohols

Zakharkin, L. I.; Stanko, V. I.; Brattsev, V. A., Izvestiya Akademii Nauk SSSR, 1964, (5), 931-2

合成路线：1 步

1720-37-2

_86%

反应条件：

1.1 Catalysts: Ammonium nitrate

参考文献：

Microwave thermolysis. V. A rapid and selective method for the cleavage of THP ethers, acetals and acetonides using clay supported ammonium nitrate "Clayan" in dry media

Meshram, H. M.; Sumithra, G.; Reddy, G. S.; Ganesh, Y. S. S.; Yadav, J. S., Synthetic Communications, 1999, 29(16), 2807-2815

合成路线：1 步

_85%

反应条件：

1.1 Reagents: Ammonia , Sodium amide Catalysts: Ferric nitrate
1.2 Reagents: Ammonium chloride

参考文献：

Efficient synthesis of 8,11-dimethylene-bicyclo[5.3.1]undecan-2-one

Gu, Haining; Xu, Wei Ming; Kinstle, Thomas H., Tetrahedron Letters, 2005, 46(38), 6449-6451

合成路线：1 步

_85%

反应条件：

1.1 Reagents: Ethylenediamine , Lithium Solvents: Tetrahydrofuran

参考文献：

Synthesis of exo-brevicomins, the aggregation pheromone of bark beetle

Zhu, Jin; Wang, Shumei; Feng, Liugui; Teng, Youwei, Hecheng Huaxue, 1993, 1(1), 35-8

合成路线：1 步

_84%

反应条件：

1.1 Reagents: 1,3-Propanediamine , Lithium ; 1 h, 70 °C; 70 °C → rt
1.2 Reagents: Potassium tert-butoxide ; 20 min, rt
1.3 10 min, rt; 3 h, rt

参考文献：

Synthesis of α,β-unsaturated epoxy ketones utilizing a bifunctional sulfonium/phosphonium ylide

Eskandari, Roozbeh; Hess, Jeremy P.; Tochtrop, Gregory P., Chemical Communications (Cambridge, 2021, 57(58), 7136-7139

合成路线：1 步

_83%

反应条件：

1.1 Reagents: 1,3-Propanediamine , Lithium ; 30 min, rt; 3 h, rt → 70 °C; 70 °C → rt
1.2 Reagents: Potassium tert-butoxide ; rt; 30 min, rt
1.3 rt; 1 h, rt
1.4 Reagents: Water ; cooled

参考文献：

Method for synthesis of pine moth pheromone

, China, , ,

合成路线：1 步

108207-99-4

_83%

反应条件：

1.1 Reagents: Sodium amide Solvents: Ammonia

参考文献：

Synthesis and reactivity of ω-functionalized propargylic silanes. Preparation of 3-vinylideneoxolanes, -oxanes, -oxepanes, and -oxocanes

Pornet, J.; Damour, D.; Miginiac, L., Tetrahedron, 1986, 42(7), 2017-24

合成路线：1 步

53293-00-8

_82%

反应条件：

1.1 Reagents: S,S-Di-2-pyridinyl carbonodithioate ; 3 - 12 h, 65 °C
1.2 Reagents: Sodium borohydride Solvents: Ethanol , Water ; 10 min, 0 °C; 0 °C → rt; 0.25 - 4 h, rt
1.3 Reagents: Hydrochloric acid Solvents: Water ; neutralized, rt

参考文献：

Facile, green, and functional group-tolerant reductions of carboxylic acids...in, or with, water

Iyer, Karthik S.; Nelson, Chandler; Lipshutz, Bruce H., Green Chemistry, 2023, 25(7), 2663-2671

合成路线：1 步

90965-06-3

4221-03-8

_82%

反应条件：

1.1 Reagents: Potassium carbonate Solvents: Methanol ; 5.5 h, rt

参考文献：

Syntheses and biological evaluation of 1,2,3-triazole and 1,3,4-oxadiazole derivatives of imatinib

Li, Yong-Tao; Wang, Jing-Han; Pan, Cheng-Wen; Meng, Fan-Fei; Chu, Xiao-Qian; et al, Bioorganic & Medicinal Chemistry Letters, 2016, 26(5), 1419-1427

合成路线：1 步

53293-00-8

_82%

反应条件：

1.1 Reagents: Lithium aluminum hydride Solvents: Tetrahydrofuran ; 0 °C → rt; 15 h, rt

参考文献：

Phase Separation As a Strategy Toward Controlling Dilution Effects in Macrocyclic Glaser-Hay Couplings

Bedard, Anne-Catherine; Collins, Shawn K., Journal of the American Chemical Society, 2011, 133(49), 19976-19981

合成路线：1 步

123186-35-6

_80%

反应条件：

1.1 Reagents: Phosphorus oxychloride Solvents: 1,2-Dichloroethane ; 50 min, rt
1.2 Reagents: Water ; cooled

参考文献：

A convenient approach for the deprotection and scavenging of the PMB group using POCl3

Ilangovan, Andivelu; Saravanakumar, Shanmugasundar; Malayappasamy, Subramani; Manickam, Govindaswamy, RSC Advances, 2013, 3(34), 14814-14828

合成路线：1 步

_75%

参考文献：

Enantiospecific synthesis of 14S,15S leukotriene A4 methyl ester

Rao, A. V. Rama; Purandare, A. V.; Singh, A. K., Bioorganic & Medicinal Chemistry Letters, 1991, 1(4), 201-4

合成路线：1 步

_70%

反应条件：

1.1 Reagents: Sodium Solvents: Ammonia

参考文献：

Intramolecular Allylsilane-Addition to Chiral Alkylidine-1,3-dicarbonyl Compounds in the Synthesis of Enantiomerically Enriched trans-1,2-Disubstituted Cyclopentanes and Cyclohexanes

Schuenke, Christian, 1996, , ,

合成路线：1 步

_69%

反应条件：

1.1 Reagents: Sodium Catalysts: Iron nitrate (Fe(NO3)3) nonahydrate Solvents: Ammonia

参考文献：

Ene-Reactions and Allylsilane Cyclization for High Diastereoselective Construction of Cyclopentane- and Cyclohexane- Derivatives

Ruther, Michael, 1990, , ,

合成路线：1 步

_67%

反应条件：

1.1 Reagents: Sodium amide ; 1 h, -40 °C; 3 h, -40 °C
1.2 Solvents: Water ; rt

参考文献：

Self-assembly and solid-state polymerization of butadiyne derivatives with amide and trialkoxyphenyl groups

Kikuchi, Kohei; Tatewaki, Yoko; Okada, Shuji, Bulletin of the Chemical Society of Japan, 2017, 90(3), 298-305

合成路线：1 步

_62%