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Pentaerythritols chiral spiro compound and synthesis and resolution method thereof

A technology of spiro compound and pentaerythritol, which is applied in the field of synthesis and resolution of spiro compound, can solve the problems of complex post-processing, corrosion equipment, and many side reactions, and achieve the effects of low cost, increased safety, and simple operation

Inactive Publication Date: 2009-02-04
TIANJIN UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The advantages of the traditional synthesis method are that the catalyst is cheap and easy to obtain, and the product yield is high, but there are disadvantages such as long process, corrosive equipment, complicated post-treatment, many side reactions, and serious environmental pollution.

Method used

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  • Pentaerythritols chiral spiro compound and synthesis and resolution method thereof
  • Pentaerythritols chiral spiro compound and synthesis and resolution method thereof
  • Pentaerythritols chiral spiro compound and synthesis and resolution method thereof

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Embodiment 1

[0034] Embodiment 1: A kind of pentaerythritol chiral spiro compound, its name and structural formula are as follows:

[0035]

[0036] 3,9-bis(4-formylphenyl)-2,4,8,10-tetraoxa-spiro[5.5]-undecane,

[0037] The raw materials it adopts are substituted benzaldehyde and pentaerythritol, and the specific reaction equation is as follows:

[0038]

[0039] The specific synthesis steps are: take the substituted benzaldehyde and pentaerythritol in a ratio of 1:5, put the pentaerythritol into 120 mL of water, dissolve the substituted benzaldehyde in a small amount of ethanol, select 8 mL of HCl as the catalyst, and stir it mechanically for 8 hours. Filter, dry, and recrystallize with ethanol to obtain a light yellow solid.

[0040] Wherein the synthetic raw material of substituted benzaldehyde is terephthalaldehyde and acetic anhydride, and concrete reaction equation is as follows:

[0041]

[0042] The specific synthesis steps are as follows: dissolve terephthalaldehyde an...

Embodiment 2

[0049] Embodiment 2: a kind of pentaerythritol chiral spiro compound, its name and structural formula are as follows:

[0050]

[0051] 3,9-Diphenyl-2,4,8,10-tetraoxa-spiro[5.5]-undecane,

[0052] The raw materials it uses are benzaldehyde and pentaerythritol. The specific reaction equation is as follows:

[0053]

[0054] The specific synthesis includes the following steps: put benzaldehyde and pentaerythritol in a ratio of 2:1 into a three-necked flask containing 120 mL, pour 15 mL of HCl as a catalyst into the three-necked flask, stir at room temperature for 8 hours, filter, and The filter cake was recrystallized to give 3,9-diphenyl-2,4,8,10-tetraoxa-spiro[5.5]-undecane as white crystals.

[0055] The resolution method of 3,9-diphenyl-2,4,8,10-tetraoxa-spiro[5.5]-undecane comprises the following steps:

[0056] (1) Dissolve 0.2 g of 2,9-diphenyl-2,4,8,10-tetraoxa-spiro[5.5]-undecane in the mobile phase as n-hexane:isopropanol=98:2 middle;

[0057] (2) Using amylo...

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Abstract

A pentaerythritol chiral spirocyclic compound is characterized by being a chiral spirocyclic compound which can be compounded by substituted benzaldehyde and pentaerythritol, also can be split and contains the construction unit of pentaerythritol. The synthetic method comprises the procedures of charging materials, adding with a catalytic agent, stirring, filtering, recrystallizing, etc. The splitting method is as follows: the compound is dissolved in a moving phase, and chiral separation is carried out on the compound in a high-effective liquid chromatograph by a chiral column. The invention has the advantages that the chiral spirocyclic compound can be used as the intermediate compound of a novel chiral axial medicine and also can be used as a medicine monomer to be induced in different active functional groups; pure optical isomer is obtained by splitting an external racemic body, thereby improving the safety of medince and having significance in pharmacodynamics and medicine dosage. In the synthetic process, an environement friendly synthetic method is applied, thereby having low cost and convenient operation, and being beneficial to protecting environment and belonging to green chemistry.

Description

(1) Technical field: [0001] The invention relates to a synthesis and resolution method of a spiro compound, in particular to a pentaerythritol chiral spiro compound and a synthesis and resolution method thereof. (two) background technology: [0002] Since the synthesis process of many drugs involves chiral matching between drugs and macromolecules in the body, the research and development of chiral drugs has become a new field of research and development in the pharmaceutical industry. Chiral drugs refer to the stereoisomers (including enantiomers and diastereoisomers) of chemical drugs containing chiral factors. , Toxic and side effects caused by significant differences. In the 1960s, Germany marketed a very effective non-barbiturate sedative drug named "reactin" for the treatment of pregnancy reactions in pregnant women. The drug was sold to 46 countries, resulting in more than 8,000 babies with seals Limb deformity, this is the reaction that shocked the world. Later st...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/10C07B57/00
Inventor 魏荣宝刘秀明李洪波
Owner TIANJIN UNIVERSITY OF TECHNOLOGY
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