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A kind of preparation method of allene compound containing ferrocene and phosphate group

A dimethyl phosphate allene and phosphate-based technology, which is applied in chemical instruments and methods, metallocenes, organic chemistry, etc., can solve the problems that there are no reports on the synthesis of allene compounds, and achieve high yield and fast synthesis rate , the effect of easy operation

Inactive Publication Date: 2019-04-12
INNER MONGOLIA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there is no report on the synthesis of allene compounds containing ferrocene and phosphate groups in the literature.

Method used

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  • A kind of preparation method of allene compound containing ferrocene and phosphate group
  • A kind of preparation method of allene compound containing ferrocene and phosphate group
  • A kind of preparation method of allene compound containing ferrocene and phosphate group

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Synthesis of 1-phenyl-3-ferrocenyl-1-phosphate dimethyl allene

[0025] Into a 25 mL glass reaction vial, add 58 mg (ie 0.26 mmol) dimethyl benzyl phosphate diazo, 42 mg (ie 0.2 mmol) ferroceneacetylene, 7.6 mg (ie 0.04 mmol) cuprous iodide and 40 mg (that is, 0.4 mmol) triethylamine, then add 2 mL of dioxane, under the protection of nitrogen, the temperature is 70 ° C, the reaction is stirred for 1 hour, after the reaction is concentrated, the volume ratio of petroleum ether: ethyl acetate is 1:1 As eluent, purified by silica gel column chromatography to obtain 1-phenyl-3-ferrocenyl-1-phosphate dimethyl allene, its structure is shown in the following formula:

[0026]

[0027] The compound is an orange-yellow liquid with a yield of 66%, and its NMR data are as follows:

[0028] 1 H NMR (500 MHz, CDCl 3 ) δ 3.80 (t, J = 5.0 Hz, 3H), 3.83 (t, J = 5.0Hz, 3H), 4.21 (s, 5H), 4.26 (d, J = 1.5 Hz, 2H), 4.33 (d, J = 12 Hz, 2H),6.51 (d, J = 12.5 Hz, 1H), 7.29 (d, J = 7 H...

Embodiment 2

[0030] Synthesis of 1-(4-chlorophenyl)-3-ferrocenyl-1-phosphate dimethyl allene

[0031] Add 68 mg (ie 0.26 mmol) dimethyl p-chlorobenzyldiazophosphate, 42 mg (ie 0.2 mmol) ferroceneacetylene, 7.6 mg (ie 0.04 mmol) cuprous iodide to a 25 mL glass reaction vial and 40 mg (that is, 0.4 mmol) triethylamine, and then add 2 mL of dioxane, under the protection of nitrogen, the temperature is 70 ° C, react and stir for 2 hours, after the reaction, concentrate, and the volume ratio of petroleum ether: ethyl acetate is 1 :1 can be used as eluent and purified by silica gel column chromatography to obtain 1-(4-chlorophenyl)-3-ferrocenyl-1-phosphate dimethyl allene, and its structure is shown in the following formula:

[0032]

[0033] The compound is an orange-yellow liquid with a yield of 57%, and its NMR data are as follows:

[0034] 1 H NMR (500 MHz, CDCl 3 ) δ 3.80 (t, J = 4.0 Hz, 3H), 3.82 (t, J = 2.0Hz, 3H), 4.21 (s, 5H), 4.27 (t, J = 1.5Hz, 2H), 4.30-4.33 (m , 2H), 6.52 (d,...

Embodiment 3

[0036] Synthesis of 1-(4-methylphenyl)-3-ferrocenyl-1-phosphate dimethyl allene

[0037] Add 63 mg (ie 0.26 mmol) dimethyl benzyl phosphate diazonium, 42 mg (ie 0.2 mmol) ferroceneacetylene, 7.6 mg (ie 0.04 mmol) cuprous iodide to a 25 mL glass reaction vial and 40 mg (that is, 0.4 mmol) triethylamine, then add 2 mL of dioxane, under the protection of nitrogen, the temperature is 80 ° C and stirred for 2 hours, concentrated after the reaction, and the volume ratio of petroleum ether: ethyl acetate is 1 :1 can be used as eluent and purified by silica gel column chromatography to obtain 1-(4-methylphenyl)-3-ferrocenyl-1-phosphate dimethyl allene, and its structure is shown in the following formula:

[0038]

[0039] The compound is an orange-yellow liquid with a yield of 83%, and its NMR data are as follows:

[0040] 1 H NMR (500 MHz, CDCl 3 ) δ 2.34 (s, 3H), 3.78 (t, J = 4.0 Hz, 3H), 3.82(t, J = 5.75, 3H), 4.21 (s, 5H), 4.25 (t, J = 2.0 Hz, 2H) , 4.30-4.33 (m, 2H),6.48 (...

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Abstract

The invention discloses a preparation method of an allene compound containing ferrocene and phosphate groups. The preparation method comprises the step of reacting aryl diazonium phosphate and ethynylferrocene in an organic solvent under catalysis of copper iodide and in the presence of alkali to obtain various allene compounds containing the ferrocene and phosphate groups. The preparation method is easy and simple in reaction operation; raw materials are easy to obtain; a reaction rate is high; product specificity is good; byproducts are few; a yield is high; and the tolerance to a functional group is good. The simple, convenient and efficient preparation method of the allene compound containing the ferrocene and phosphate groups is provided for the first time.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a preparation method of an allene compound containing ferrocene and phosphate groups. Background technique [0002] Allene compounds play a vital role in the fields of organic synthesis and even polymer materials. Allene compounds are not only widely used as intermediates in the synthesis of additives, dyes, etc., but also their polymers and even copolymers can also be used in many industries such as fibers and paints. In recent years, many new reactions using allenes as substrates have been developed, many of which have been successfully applied in the synthesis of natural products. On the other hand, since both ferrocene and phosphate groups have interesting biological properties, the simultaneous introduction of ferrocene and phosphate groups into allenes is very important for the development of new biological activities, new drug development and new materials. Synthesis is ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F17/02
CPCC07F17/02
Inventor 陈树峰赵婉荣吴新星
Owner INNER MONGOLIA UNIVERSITY
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