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Cis-1-halo-2-chloroalkene and preparation method and application thereof

A chlorinated olefin, cis technology, applied in the field of cis-1-halo-2-chloroalkene and its preparation, can solve problems such as powerlessness, reduce environmental pollution, reduce "three wastes" emissions, economic benefits and social significant effect

Inactive Publication Date: 2013-11-27
ZHEJIANG NORMAL UNIVERSITY +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Although the Wittig reaction and olefin metathesis have been well used for the synthesis of some trans double bonds, it is still difficult for cis-disubstituted alkenes, cis-trisubstituted or cis-tetrasubstituted alkenes powerless

Method used

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  • Cis-1-halo-2-chloroalkene and preparation method and application thereof
  • Cis-1-halo-2-chloroalkene and preparation method and application thereof
  • Cis-1-halo-2-chloroalkene and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051]Lithium chloride (26mg, 0.6mmol) and palladium acetate (5.6mg, 0.025mmol) were added in a 10mL round bottom flask, 1mL of acetic acid was added to dissolve, then phenylacetylene chloride (73mg, 0.5mmol) and Allenyl ester (17.4 mg, 0.1 mmol). The reaction system was reacted at 60° C. for 5 hours, quenched by adding 5 mL of water, and extracted three times with ethyl acetate (10 mL). After the combined organic phases were washed with sodium bicarbonate solution and saturated brine, the organic layer obtained was dried over anhydrous sodium sulfate, and then the solvent was removed by rotary evaporation, and then separated by silica gel (300-400 mesh) column chromatography (eluent: petroleum ether) to obtain 71 mg of cis-1,2-dichlorostyrene (yield: 82%) as a colorless liquid.

[0052] colorless liquid 1 H-NMR (CDCl 3 , 400MHz): δ6.70(s, 1H), 7.38-7.40(m, 3H), 7.53-7.55(m, 2H); 13 C-NMR (CDCl 3 , 100MHz): δ116.1, 126.6(2C), 128.7(2C), 129.5, 135.6, 135.8; MS(EI, m / z): 1...

Embodiment 2

[0055] Except that the palladium acetate of 0.01 mmol is used to replace the palladium acetate of 0.025 mmol in Example 1 as the catalyst, all the other operating steps are the same as in Example 1 to obtain cis-1,2-dichlorostyrene with a yield of 81%, product characterization data With embodiment 1.

Embodiment 3

[0057] Except that the phenylacetylene chloride in Example 1 was replaced by 4-fluorophenylacetylene chloride, the remaining operation steps were the same as in Example 1, yield: 68%, product: colorless liquid. colorless liquid 1 H-NMR (CDCl 3 , 400MHz): δ6.65(s, 1H), 7.08(t, J=8.4Hz, 2H), 7.50-7.54(m, 2H); 13 C-NMR (CDCl 3 , 100MHz): δ115.7(d, J=21.9Hz, 2C), 115.9(d, J=1.6Hz, 1C), 128.5(d, J=8.4Hz, 2C), 132.0(d, J=3.3Hz , 1C), 134.6, 162.8 (d, J=248.6Hz, 1C); MS (EI, m / z): 194(6), 192(38), 190(M + , 58), 157(32), 155(M + - 35 Cl, 100). It shows that the colorless liquid is cis-1,2-dichloro-2-p-fluorostyrene represented by structural formula 3b.

[0058]

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Abstract

The invention discloses a cis-1-halo-2-chloroalkene compound. The compound has a constitutional formula I in the description. The invention also provides a selective synthesis method for the cis-1-halo-2-chloroalkene and the application of the cis-1-halo-2-chloroalkene in the synthesis of multi-substituted aromatic hydrocarbon, the preparation of Z-trisubstituted alkene and the synthesis of Z-trisubstituted alkene-containing medical intermediate and natural product. On the basis, the inventer achieves a new vitamin A synthesis route. By means of selective implementation, the invention increases the atom economy of chemical reaction, is easy to operate, is environment-friendly, and has high practical value.

Description

technical field [0001] The invention relates to the field of chemical synthesis, in particular to a cis-1-halo-2-chloroalkene and its preparation method and application. Background technique [0002] Multi-substituted alkenes are widely found in natural products such as vitamins, prostaglandins, and insect pheromones, as well as pharmaceutical and chemical intermediates. Therefore, the synthesis of multi-substituted alkenes is one of the important contents of organic chemistry. Among them, regio- and stereoselective synthesis Multi-substituted alkenes are a very challenging subject. [0003] The synthesis of existing multi-substituted alkenes generally includes the following three approaches a, b and c: [0004] [0005] Although the Wittig reaction and olefin metathesis have been well used for the synthesis of some trans double bonds, it is still difficult for cis-disubstituted alkenes, cis-trisubstituted or cis-tetrasubstituted alkenes powerless. In recent years, a m...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C22/04C07C22/02C07C25/28C07C21/04C07C17/00C07C43/225C07C43/174C07C41/22C07D333/12C07B39/00C07C69/76C07C67/347C07C15/48C07C2/88C07C403/08
Inventor 朱钢国陈东旭
Owner ZHEJIANG NORMAL UNIVERSITY
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