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Method for synthesizing spiro ketal by employing double organic zincons

A technology of spiro ketal and organozinc, which is applied in the field of organic synthesis to achieve the effects of shortening the synthesis cycle, easily obtaining raw materials, and mild reaction conditions

Inactive Publication Date: 2010-09-29
NORTHWEST NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, none of the currently completed synthetic methods can provide more than 4 mg of product

Method used

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  • Method for synthesizing spiro ketal by employing double organic zincons
  • Method for synthesizing spiro ketal by employing double organic zincons
  • Method for synthesizing spiro ketal by employing double organic zincons

Examples

Experimental program
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Effect test

Embodiment 1

[0030] Embodiment 1, reaction equation is as follows:

[0031]

[0032] 1. Preparation of double organozinc reagents with ketal

[0033] Add dry NaI (0.6mol), dry 100ml acetone and 1,7-dichloro-4-heptanone (compound 1) (0.2mol) into a single-necked flask, and install a reflux condenser to reflux for 8h. After cooling, evaporate the acetone, then add 100ml of ether to dissolve the product, filter off NaCl and excess NaI, and evaporate the solvent to obtain the crude product. Finally, recrystallization with methanol gave white crystals (compound 2) (mp: 41-42°C). The yield was 99%.

[0034] Then add 1,7-diiodo-4-heptanone (0.025mol), ethylene glycol (0.03mol), p-toluenesulfonic acid (0.001mol) and 60ml benzene in a single-necked flask, and then install the water separator and reflux Condenser, fill the water separator with benzene, heat to reflux until about 0.5ml of water is separated, it takes about 2 hours. Stop heating, add 0.3g of potassium carbonate and stir for 2h ...

Embodiment 2

[0046] Embodiment 2, reaction equation are as follows:

[0047]

[0048] 1. Preparation of double organozinc reagents with ketal

[0049] The preparation method is the same as in Example 1.

[0050] 2. Synthesis of diketone compound 5

[0051] Add zinc powder (0.11mol, 7.1g) into a reactor, protect it with argon, add 10mlTHF, stir, then add 1ml1,2-dibromoethane, heat it to reflux until foaming, cool to room temperature and add 1ml of trimethylchlorosilane (1,2-dibromoethane and trimethylchlorosilane are used to activate zinc powder), after stirring for 15min, a solution of compound 3 (0.05mol) in THF (80ml) was added. Heat it to keep the temperature at 35-40°C, and after about 3 hours, the zinc powder disappears to obtain a THF solution of compound 4, which is cooled to room temperature for later use.

[0052] Add dry CuCN (0.1mol) and dry LiCl (0.2mol) to another reactor, protect it with argon, add 80ml THF, stir, wait for it to dissolve and cool to -30°C, slowly add th...

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Abstract

The present invention discloses a method of synthesizing spiro ketal by dual-organic zinc reagent. The method is that the dual-organic zinc iodide with ketal is used to react with acyl chloride to produce the diketone with ketal to be deoxidized and synthesized as dihydroxy ketal by sodium borohydride, and then the spiro ketal is further synthesized under the catalysis of p-toluenesulfonic acid. The present invention shortens the synthesis route of the spiro ketal greatly and at the same time reduces the synthesis cost; the reaction yield is high, and the total yield is 24 percent to 38 percent; the reaction condition is gentle; the operation is simple; the present invention is easy for the industrialized production.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and relates to a method for synthesizing spiro ketals, in particular to a method for synthesizing spiro ketals by using double organozinc reagents. Background technique [0002] Natural products are of great significance for the discovery, design and synthesis of new drugs. In fact, 40% of the applied drugs are derived from natural products and their derivatives, and the proportion of drugs for treating cancer is as high as 60%. However, due to the very small content of some natural products in nature, and from the perspective of ecological protection, it is impossible for people to obtain sufficient amounts from nature for use in medicine. Therefore, for some natural products with good medicinal effects, they can only be artificially synthesized. [0003] The structure of spiro ketal widely exists in natural products, especially in some natural products with anticancer activity extrac...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D493/10
Inventor 胡雨来徐长明黄丹凤牛腾王海峰李贵花
Owner NORTHWEST NORMAL UNIVERSITY
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