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A gem-difluoro-substituted tetralone compound and its preparation method

A technology of tetralone and compound, applied in the field of geminal difluoro-substituted tetralone compound and preparation thereof, can solve the problems of compound synthesis literature report and the like, and achieve the effects of high yield, mild conditions and simple preparation steps

Active Publication Date: 2022-03-04
SHANGHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In view of the special biological activity of compounds containing difluoromethylene structure, but there is no related synthesis of gem-difluoro-18-methyl norethindrone or gem-difluoroamine carbaryl or gem-diflusertraline. Literature report

Method used

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  • A gem-difluoro-substituted tetralone compound and its preparation method
  • A gem-difluoro-substituted tetralone compound and its preparation method
  • A gem-difluoro-substituted tetralone compound and its preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Example 1 Preparation of 2,2-difluoro-4-hexyl-3,4-dihydro-1-naphthalenone (A1)

[0035]

[0036] Step 1: with phenyl ethyl ketone (0.1mol, 1.0 equivalent, 12.0g) and ethyl trifluoroacetate (0.12mol, 1.2 equivalent, 17.0g) in the presence of NaH (0.15mol, 1.5 equivalent, 6.0g) 4,4,4-trifluoro-3-hydroxy-1-but-2-ene-1-acetophenone was obtained by reacting in 120 mL ether solvent. TLC (developing agent is petroleum ether / ethyl acetate=5 / 1) detects that the reaction is complete, 50 mL of water is added to the system to quench, and the pH is adjusted to 2-3 with (1M hydrochloric acid) dilute hydrochloric acid, and the reaction system is washed with ethyl acetate ( 3×50mL) extraction. The combined organic layers were washed with saturated brine (saturated NaCl), washed with Na 2 SO 4 Dry and concentrate in vacuo to obtain crude 4,4,4-trifluoro-3-hydroxyl-1-but-2-ene-1-acetophenone, which is directly used in step 2.

[0037] Step 2: Dissolve crude 4,4,4-trifluoro-3-hydro...

Embodiment 2

[0042] Example 2 Preparation of 2,2-difluoro-4-(phenoxy)-methyl-3,4-dihydro-1-naphthalenone (A2)

[0043]

[0044] Step 1: With phenyl ethyl ketone (0.1mol, 1.0 equivalent, 12.0g) and ethyl trifluoroacetate (0.12mol, 1.2 equivalent, 17.0g) in the presence of NaH (0.15mol, 1.5 equivalent, 6.0g) ( In 120mL diethyl ether solvent) to obtain 4,4,4-trifluoro-3-hydroxyl-1-but-2-ene-1-acetophenone. TLC (developing agent is petroleum ether / ethyl acetate=5 / 1) detects that the reaction is complete, 50 mL of water is added to the system to quench, and the pH is adjusted to 2-3 with (1M hydrochloric acid) dilute hydrochloric acid, and the reaction system is washed with ethyl acetate ( 3×50mL) extraction. The combined organic layers were washed with saturated brine (saturated NaCl), washed with Na 2 SO 4 Dry and concentrate in vacuo to obtain crude 4,4,4-trifluoro-3-hydroxyl-1-but-2-ene-1-acetophenone, which is directly used in step 2.

[0045] Step 2: Dissolve crude 4,4,4-trifluoro-...

Embodiment 3

[0049] Example 3 Preparation of 4-(butoxy)-methyl-2,2-difluoro-3,4-dihydro-1-naphthalenone (A3)

[0050]

[0051] Step 1: Take phenylethanone (0.1mol, 1.0eq, 12.0g) and ethyl trifluoroacetate (0.12mol, 1.2eq, 17.0g) in the presence of NaH (0.15mol, 1.5eq, 6.0g) in 120mL Reaction in ether solvent gives 4,4,4-trifluoro-3-hydroxyl-1-but-2-ene-1-acetophenone. TLC (developing agent is petroleum ether / ethyl acetate=5 / 1) detects that the reaction is complete, 50mL of water is added to the system to quench, the pH is adjusted to 2-3 with 1M dilute hydrochloric acid, and the reaction system is washed with ethyl acetate (3×50mL )extraction. The combined organic layers were washed with saturated brine (saturated NaCl), washed with Na 2 SO 4 Dry and concentrate in vacuo to obtain crude 4,4,4-trifluoro-3-hydroxyl-1-but-2-ene-1-acetophenone, which is directly used in step 2.

[0052] Step 2: Dissolve crude 4,4,4-trifluoro-3-hydroxy-1-but-2-ene-1-acetophenone (0.1mol, 1.0eq) in 250mL ...

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Abstract

The invention provides a gem-difluoro-substituted tetralone compound and a preparation method thereof. The gem-difluoro-substituted tetralone compound is characterized in that its structure is as shown in general formula (I): wherein: Ar is selected from naphthyl, thienyl, phenyl, m-, p-, ortho-alkane Base substituted phenyl, m, p, ortho halogen substituted phenyl, m, p, ortho trifluoromethyl substituted phenyl, m, p, ortho cyano substituted phenyl; R 1 It is selected from alkyl, substituted alkyl, benzyl, phenyl, substituted phenyl, carboxylate. The invention has simple preparation steps, mild conditions and high yield.

Description

technical field [0001] The invention relates to the technical field of pharmacy, in particular to a gem-difluoro-substituted tetralone compound and a preparation method thereof. Background technique [0002] Tetralone compounds are important basic chemical raw materials and pharmaceutical intermediates, and are widely used in many fields such as pesticides, medicines and auxiliaries. Drug intermediates such as norethindrone intermediates, insecticide carbaryl and antidepressant sertraline (as shown in the following formula) can also be used as solvents and plastic softeners. In particular, using it as a raw material to further synthesize fused-ring aromatic compounds and steroidal compounds has attracted widespread attention. [0003] [0004] Since difluoromethylene (–CF 2 –) has good metabolic stability, it is often regarded as bioisosteres of oxygen atoms, carbonyl groups and in some functionalized difluoromethylated structures. Since the difluoromethylene structure...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C49/697C07C49/755C07C69/757C07D333/54C07C45/69C07C67/347
Inventor 吴晶晶彭朋黄国志王星吴范宏
Owner SHANGHAI INST OF TECH