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Acetylenic compounds

A compound and selected technology, applied in the field of acetylenic compounds, can solve the problem of PDA color transformation that is not fully understood

Inactive Publication Date: 2009-09-30
COMMONWEALTH SCI & IND RES ORG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The mechanism by which PDA color transformations follow is still not fully understood

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0272] Part A: 11-Trimethylsilyl-undec-10-ynoic acid

[0273]

[0274] Use n-BuLi (1.6M hexane solution, 37.72ml, 60.35mmol, 2.2 molar equivalent) to -78 ℃ undec-10-ynoic acid (5g, 27.43mmol) in anhydrous THF solution (200ml) deal with. After stirring for 2 minutes, trimethylsilyl chloride (10.76ml, 85.04mmol, 9.24g, 3.1 molar equivalent) was added. The reaction mixture was slowly warmed to 25°C and stirred for 1 hour. The reaction was quenched by adding 2N HCl aqueous solution (50ml), and using CH 2 Cl 2 (3×50ml) extraction. Na for organic layer 2 SO 4 Dry, filter and concentrate. Column chromatography (SiO 2 , EtOAc-hexane 2:1) to obtain the acid in the form of a white solid (5.3g, 20.83mmol, 76%): 1 H-NMR(CDCl 3 , 400MHz): δ [ppm] = 0.61 (9H, s), 1.17-1.39 (8H, m), 1.41-1.53 ​​(2H, m), 1.55-1.68 (2H, m), 2.17 (2H, t, J =6.5Hz), 2.35(2H, t, J=6.5Hz)

[0275] Part B: Synthesis of 2-hydroxy-11-trimethylsilyl-undec-10-ynoic acid

[0276]

[0277] Dry diisopropylamine (6.71ml, 4...

Embodiment 2

[0295] Part A: Synthesis of pentadec-8,10-diyn-1-ol

[0296]

[0297] In a nitrogen atmosphere, to a stirred solution of 1-iodo-1-hexyne (6.2g, 29.80mmol) and 8-nonyn-1-ol (2.46g, 17.53mmol) in pyrrolidine (50ml) was added iodide Copper (I) (2.98 mmol, 0.57 g). After stirring for 30 minutes at room temperature, the mixture was hydrolyzed with saturated aqueous ammonium chloride solution and extracted with diethyl ether. MgSO for organic extracts 4 Dry and remove the solvent in vacuo. Column chromatography (SiO 2 , EtOAc-hexane: 2:1) to obtain 3.35 g (15.19 mmol, 87%) of pure pentadec-8,10-diyn-1-ol.

[0298] 1 H-NMR(CDCl 3 , 400MHz): δ [ppm] = 0.89 (3H, t, J = 7.3 Hz), 1.26-1.62 (14H, m), 2.24 (4H, t, J = 6.6 Hz), 3.62 (2H, t, J = 7.0Hz)

[0299] Part B: Synthesis of 15-iodo-pentadec-5,7-diyne

[0300]

[0301] At -10°C, the CH of pentadec-8,10-diyn-1-ol (2.6g, 11.80mmol), triphenylphosphine (3.4g, 12.98mmol) and imidazole (0.96g, 14.16mmol) 2 Cl 2 (60ml) Add a small amount of...

Embodiment 3

[0324] Part A: 2-hydroxy-heptadecene-10,12-diyl acid crystal

[0325] In a vacuum, at 40°C, reduce the volume of a methanol solution (30ml) of 2-hydroxy-heptadecene-10,12-diynoic acid (100mg, 0.36mmol) to 1ml, and add a tetrahydrofuran solution of hydrochloric acid to it (20ml 1M aqueous HCl in 20ml THF). The solution was stirred overnight at room temperature, then the solvent was removed to obtain a clear oil. It was dissolved in dichloromethane (1ml), and then hexane was introduced by slow vapor diffusion in a closed system at -10°C. After 3 days, well-formed crystals of 2-hydroxy-heptadediynoic acid appeared in dichloromethane.

[0326] Part B: Polymerization of 2-Hydroxy-Heptadecene-10,12-Diynoic Acid Single Crystal

[0327] Take several single crystals prepared as described in Part A above and expose them to UV radiation (254 nm) from a small hand-held lamp. After a few seconds of exposure, the crystals turned dark blue. When exposed to organic solvents or high temperatures, ...

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Abstract

The present invention relates to a class of acetylenic compounds, to a method of preparing the acetylenic compounds, and to the polymerisation and therapeutic uses of the acetylenic compounds. The invention particularly relates to compounds containing two acetylenic moieties.

Description

Technical field [0001] The invention relates to a class of acetylenic compounds, a method for preparing the acetylenic compounds, and the polymerization and therapeutic uses of the acetylenic compounds. The present invention particularly relates to compounds containing two acetylenic moieties. Background technique [0002] It is known that compounds containing two acetylenic moieties (ie, diacetylenic compounds) exhibit a series of interesting properties. For example, a series of compounds containing a 3-ene-1,5-diyne structure, called enediyne compounds, show strong antibacterial and anticancer properties. And it has been reported that many diacetylenols have cytotoxicity. [0003] In addition to exhibiting biological activity, diacetylenic compounds have been used to prepare monomers for polymeric materials. A unique class of polymeric materials that can be prepared from diacetylene compounds is called polydiacetylene (PDA). PDA is usually made from conjugated diacetylene compo...

Claims

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Application Information

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IPC IPC(8): C07C69/22C07C69/732C07C67/00C07C233/00C07B37/02C07D295/185C07D319/12A61K9/00A61P35/00
CPCC07D319/12C07C69/732C07C69/606C07D295/185C07C231/10C07C233/11A61P31/04A61P35/00A61K31/23C08G63/12C08G63/42
Inventor 安德鲁·C·沃登弗洛里安·H·M·格雷切恩迈克尔·S·奥谢
Owner COMMONWEALTH SCI & IND RES ORG
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