A kind of preparation method of macrolide precursor

A macrolide and precursor technology, which is applied in the field of preparation of macrolide precursors, can solve the problems of difficult control of reaction conditions and high degree of risk, and achieve convenient operation, easy-to-obtain substrate structure, and simple substrate structure Effect

Active Publication Date: 2020-10-02
SHANGHAI INST OF TECH
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  • Description
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Problems solved by technology

However, low temperature conditions and concentrated acid are mostly used in the preparation methods of 1,2,4,5,7,8-hexaoxa-3,6,9-tricyclohexylidenecyclononane at present, and the difficulty of controlling the reaction conditions and the degree of danger are relatively high. high

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  • A kind of preparation method of macrolide precursor
  • A kind of preparation method of macrolide precursor
  • A kind of preparation method of macrolide precursor

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[0024] The preparation method of a kind of macrolide precursor 1,2,4,5,7,8-hexaoxa-3,6,9-tricyclohexylidene cyclononane of the present invention comprises the following steps:

[0025] (1) Mix cyclohexanone and hydrogen peroxide, add an iron salt catalyst, react at 20-45°C for 1-6h, extract and concentrate after the reaction, and separate to obtain the main product;

[0026] (2) At 20-45°C, react the main product of the previous step with cyclohexanone through an organic acid catalyst for 1-3 hours, and separate and purify after the reaction to obtain 1,2,4,5,7,8-hexaoxa- 3,6,9-Tricyclohexylcyclononane.

[0027] Reaction formula of the present invention is as follows:

[0028]

Embodiment 1

[0030] Weigh 10.0mmol of cyclohexanone and 30mmol of hydrogen peroxide into the bottle, add 2mmol of ferric ammonium sulfate dodecahydrate, react at 25°C for 1h, after the reaction is completed, after extraction and concentration, ethyl acetate / petroleum ether = 1 / 5(V / V) is the eluent, and the main product 1,1'-dihydroperoxydicyclohexyl peroxide is obtained by separation by column chromatography.

[0031] Such as figure 1 As shown, the main product 1 was characterized by NMR, and the results are as follows: 1 H NMR (500MHz, CDCl 3 )δ9.55 (s, 2H), 1.87 (s, 8H), 1.61 (s, 8H), 1.48 (s, 4H).

[0032] At 25°C, the main product was mixed with equimolar cyclohexanone, and p-toluenesulfonic acid was added (based on the total moles of the main product, cyclohexanone and p-toluenesulfonic acid, the molar percentage of p-toluenesulfonic acid was 5 %) was reacted for 2 h, ethyl acetate / petroleum ether=1 / 70 (V / V) was used as the eluent, and the product was separated by column chromatog...

Embodiment 2

[0036] Weigh 10.0mmol of cyclohexanone and 30mmol of hydrogen peroxide into the bottle, add 2mmol of iron sulfate, and react for 1h at 25°C. After the reaction, after extraction and concentration, ethyl acetate / petroleum ether=1 / 5(V / V) is the eluent, and the main product 1 is obtained by column chromatography separation. At 25° C., the main product is mixed with equimolar cyclohexanone, and p-toluenesulfonic acid (based on the main product, cyclohexanone and p-toluenesulfonic acid) is added. Add the total moles of benzenesulfonic acid as the basis, and the molar percentage of p-toluenesulfonic acid is 5%) to react for 2h, ethyl acetate / petroleum ether=1 / 70 (V / V) is the eluent, and is separated by column chromatography product.

[0037] The total yield of target product 2 in this embodiment 2 is 37%.

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Abstract

The invention belongs to the technical field of organic synthesis and particularly discloses a method for preparing a macrolide precursor. The method comprises the following steps: (1) mixing cyclohexanone and hydrogen peroxide, further adding a ferric salt catalyst, carrying out a reaction for 1-8 hours at the room temperature, and carrying out column chromatography separation after the reactionis completed so as to obtain a main product 1,1'-dihydroperoxide dicyclohexyl peroxide; (2) condensing the main product with cyclohexanone under catalysis of an organic acid, and after the reaction ends, carrying out separation and purification, thereby obtaining the macrolide precursor 1,2,4,5,7,8-hexaoxa-3,6,9-tricyclohexylidene cyclononane. The cyclohexanone which is low in price and easy to obtain is adopted as a raw material, and the product is prepared through two steps of reactions under catalysis of a ferric salt and a small amount of the organic acid at 20-45 DEG C; the method is simple and convenient in process, high in yield, applicable to popularization and application, and the product prepared by using the method can be applied to fields such as a cigarette fixative agent.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to a preparation method of a macrolide precursor. Background technique [0002] 1,2,4,5,7,8-hexaoxa-3,6,9-tricyclohexylidenecyclononane is thermally unstable and has applications in many fields. Macrolides can be prepared by thermal decomposition. For example, the precursor of cyclopentadecanolactone, a fixative used in blended cigarettes. However, low temperature conditions and concentrated acid are mostly used in the preparation methods of 1,2,4,5,7,8-hexaoxa-3,6,9-tricyclohexylidenecyclononane at present, and the difficulty of controlling the reaction conditions and the degree of danger are relatively high. high. Therefore, it is of great significance to find a new method for preparing 1,2,4,5,7,8-hexaoxa-3,6,9-tricyclohexylidenecyclononane. [0003] At present, the preparation of such compounds needs to be carried out under low temperature conditions, using high-co...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D313/00
CPCC07D313/00
Inventor 孙小玲杜天宇
Owner SHANGHAI INST OF TECH
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