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An annulene derivative containing an exocyclic double bond and a preparation method thereof

A technology of derivatives and annulene, applied in the field of annulene derivatives and their preparation, can solve problems such as non-existent preparation methods and complex structures, and achieve broad application prospects and complex and diverse structures

Active Publication Date: 2016-04-13
ANHUI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Annulenene derivatives are a very important class of compounds, and there is no mature and effective preparation method for common annulene derivatives in this field, especially in the specific chemical and pharmaceutical fields. Its structure is more complex, and an efficient and stable preparation method is urgently needed in this field

Method used

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  • An annulene derivative containing an exocyclic double bond and a preparation method thereof
  • An annulene derivative containing an exocyclic double bond and a preparation method thereof
  • An annulene derivative containing an exocyclic double bond and a preparation method thereof

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Effect test

Embodiment 1

[0029] An annulene derivative containing an exocyclic double bond, the structural formula of the annulene derivative containing an exocyclic double bond is:

[0030]

[0031] Among them, E 1 =E 2 =CO 2 R;

[0032] R is straight-chain alkyl, branched-chain alkyl;

[0033] R 1 , R 2 It is halogen, straight chain alkyl, branched chain alkyl, ester group, alkoxy group and their corresponding derivatives.

[0034] Preferably, the structural formula of an annulene derivative containing an exocyclic double bond is:

[0035]

[0036] The R is isopropyl, R 1 , R 2 For methyl.

[0037] The annulene derivative containing an exocyclic double bond is a multi-substituted annulene derivative containing an exocyclic double bond.

[0038] A method for preparing an annulene derivative containing an exocyclic double bond, comprising the following steps:

[0039] a. Precursor synthesis;

[0040] (1) With sodium hydride as a catalyst, diisopropyl malonate and propargyl bromide we...

Embodiment 2

[0047] An annulene derivative of an exocyclic double bond, its structural formula is:

[0048]

[0049] where E 1 =E 2 =CO 2 R, R is straight-chain alkyl, branched-chain alkyl, saturated hydrocarbon, unsaturated hydrocarbon or aromatic hydrocarbon group; R 1 , R 2 It is halogen, straight chain alkyl, branched chain alkyl, ester group, alkoxy group and their corresponding derivatives.

[0050] A preparation method of an annulene derivative containing an exocyclic double bond, comprising the following steps:

[0051] (1) Using sodium hydride as a catalyst, diisopropyl malonate and propargyl bromide were added to anhydrous acetonitrile in an ice-water bath, stirred and reacted, and a white solid product, namely compound 1, was obtained after purification and separation;

[0052] The molar ratio of diethyl malonate to propargyl bromide is 1:2.2-3.2;

[0053] The purification and separation is to wash the product with water, extract with ethyl acetate, spin dry under reduc...

Embodiment 3

[0059] An annulene derivative containing an exocyclic double bond, the structural formula is:

[0060]

[0061] A preparation method of an annulene derivative containing an exocyclic double bond, the preparation method comprising the following steps:

[0062] a. Precursor synthesis;

[0063] b. Synthesis of the target product;

[0064] c. Purification.

[0065] Wherein, a, precursor synthesis, comprises the following steps:

[0066] (1) Using sodium hydride as a catalyst, add 200mmol diisopropyl malonate and 440mmol propargyl bromide to an ice-water bath in anhydrous acetonitrile, stir and react for 8 hours, wash the product with water, extract with ethyl acetate, and depressurize Spin to dry, column chromatography (volume ratio ethyl acetate:petroleum ether=1:100) to obtain a white solid product, namely compound 1;

[0067]

[0068] (2) Under anhydrous and oxygen-free conditions, 20mmol of compound 1, 48mmol of p-methyl iodobenzene, 842mg (1.2mmol) of PdCl 2 (PPh) ...

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Abstract

The invention relates to an annulene derivative containing exocyclic double bonds and a preparation method of the annulene derivative. The preparation method comprises the following steps: a, synthesizing a precursor; b, synthesizing a target product; c, purifying. Compared with the prior art, a brand-new synthetic method for the polysubstituted annulene derivative containing the exocyclic double bonds is provided; compared with a general annulene derivative, the prepared annulene derivative containing the exocyclic double bonds is polycyclic and relatively complicated and diversified in structure, and has a relatively wide application prospect in chemical production and clinical medicines.

Description

technical field [0001] The invention relates to the field of organic compounds, in particular to an annulene derivative containing an exocyclic double bond and a preparation method thereof. Background technique [0002] Annulenene derivatives are a very important class of compounds. There is no mature and effective preparation method for common annulenene derivatives in this field, especially in the specific chemical and pharmaceutical fields. Its structure is more complex, and an efficient and stable preparation method is urgently needed in this field. Compared with common annulene derivatives, the annulene derivatives containing exocyclic double bonds prepared by the present invention have multiple rings, their structures are more complex and diverse, and they will also show broader application prospects in chemical production and clinical medicine. Contents of the invention [0003] Aiming at the problems existing in the prior art, the object of the present invention i...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C69/753C07C67/347
CPCC07C67/347C07C69/753C07C2603/30
Inventor 胡琼潘相相谢海凤胡益民
Owner ANHUI NORMAL UNIV
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