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A kind of preparation method of high-purity cyclohexenone long-chain alcohol

A cyclohexenone long-chain alcohol and cyclohexenone technology, which is applied in the field of medicinal chemistry and synthetic chemistry, can solve the problems of high cost, difficult purification, and low melting point of column chromatography, and achieve avoidance of column chromatography and short route , good yield effect

Active Publication Date: 2022-06-28
TAIHO PHARMA CO LTD
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AI Technical Summary

Problems solved by technology

Cyclohexenone long-chain alcohols have a low melting point and are oily at high room temperature, which is difficult to purify. The cyclohexenone long-chain alcohols reported in the literature are all processed by column chromatography to obtain high-purity products. Due to the high cost of column chromatography , loss is big, is not suitable for industrialized production, therefore, it is very urgent to find a route that is short, yield is high, easy to operate, suitable for the method for the preparation of industrialized production of high-purity cyclohexenone long-chain alcohol

Method used

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  • A kind of preparation method of high-purity cyclohexenone long-chain alcohol
  • A kind of preparation method of high-purity cyclohexenone long-chain alcohol
  • A kind of preparation method of high-purity cyclohexenone long-chain alcohol

Examples

Experimental program
Comparison scheme
Effect test

preparation example 13

[0084] Preparation Example 13-isobutoxy-2,6,6-trimethylcyclohex-2-en-1-one

[0085]

[0086] 2,4,4-Trimethylcyclohexyl-1,3-dione VII (80g, 1eq) and isobutanol (76.9g, 2eq) were added to cyclohexane (400mL), and p-TSA· H 2 O (5g, 0.05eq), heated and refluxed to separate water for 16h. After-treatment, cooled to ambient temperature, washed successively with 5% sodium hydroxide (80 mL), water (80 mL) and saturated brine (80 mL), dried over anhydrous sodium sulfate, and concentrated to dryness to obtain 3-isobutoxy-2 ,6,6-Trimethylcyclohex-2-en-1-one (103.65 g, 95%). 1H NMR (400MHz, CDCl3): δ3.77 (d, 2H, J=6.4Hz), 2.55-2.58 (m, 2H), 1.95-2.05 (m, 1H), 1.82 (t, 2H, J=6.4Hz) ), 1.72(s, 3H), 1.11(s, 6H), 1.01(d, 6H, J=6.4Hz).

[0087] Preparation Example 23-cyclohexylmethoxy-2,6,6-trimethylcyclohex-2-en-1-one

[0088]

[0089] 2,4,4-Trimethylcyclohexyl-1,3-dione VII (10g, 1eq) and cyclohexylmethanol (14.8g, 2eq) were added to cyclohexane (100mL), and p-TSA· H2O (0.62g, 0....

preparation example 43-

[0093] Preparation Example 43-Methoxy-2,6,6-trimethylcyclohex-2-en-1-one

[0094]

[0095] 2,4,4-Trimethylcyclohexyl-1,3-dione VII (2.7g, 1eq) and trimethyl orthoformate (2.8g, 1.5eq) were added to methanol (40mL), p- TSA·H2O (167 mg, 0.05 eq) was stirred at room temperature overnight. After-treatment, dichloromethane (30 mL) was added to dilute, washed successively with 5% sodium hydroxide (20 mL), water (10 mL) and saturated brine (10 mL), dried over anhydrous sodium sulfate, concentrated to dryness and purified by column to obtain 3 -Methoxy-2,6,6-trimethylcyclohex-2-en-1-one (2.19 g, 74.4%). 1 HNMR (400MHz, CDCl 3 ): δ3.81(s, 3H), 2.55-2.58(m, 2H), 1.95-2.05(m, 1H), 1.82(t, 2H, J=6.4Hz), 1.72(s, 3H), 1.11( s, 6H).

[0096] Preparation Example 53,3'-(propyl-1,2-dioxo)-bis(2,6,6-trimethylcyclohexyl-2-en-1-one)

[0097]

[0098] 2,4,4-Trimethylcyclohexyl-1,3-dione VII (5g, 1eq), 1,3-propanediol (1.23g, 0.5eq), p-TSA·H2O (311mg, 0.05eq) and toluene (30 mL) were add...

preparation example 93-(1

[0109] Preparation Example 93-(15-Chloropentadecyloxy)-2,6,6-trimethylcyclohexyl-2-en-1-one

[0110]

[0111] 2,4,4-Trimethylcyclohexyl-1,3-dione VII (1.3 g, 1.1 eq) and 15-chloropentadecanol VIII-1 (2 g, 1 eq) were added to cyclohexane (50 mL) Add p-TSA·H2O (72mg, 0.05eq), heat and reflux for 16h, post-treatment, cool to ambient temperature, use 5% sodium hydroxide (20mL), water (10mL) and saturated brine ( 10 mL) washed, dried over anhydrous sodium sulfate, and concentrated to dryness to obtain 3-(15-chloropentadecyloxy)-2,6,6-trimethylcyclohexyl-2-en-1-one (2.46 g, 80.9 %). 1 H NMR (400MHz, CDCl 3 ):δ3.97(t,2H,J=6.8Hz),3.45(m,2H,J=6.8Hz),2.54-2.55(m,2H),1.78-1.84(m,4H),1.68(s, 3H), 1.39-1.41(m, 4H), 1.22-1.35(m, 21H), 1.08(s, 6H).

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Abstract

The invention relates to a preparation method of high-purity cyclohexenone long-chain alcohol represented by formula I. The compound of formula I is prepared by metal-mediated Barbier reaction. The method of the invention has the following advantages: short route, high yield, high product purity, and is suitable for industrial amplification.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry and synthetic chemistry, in particular to a preparation method of high-purity cyclohexenone long-chain alcohol. Background technique [0002] Nerve growth factor (NGF), mainly present in the hippocampus and cerebral cortex, plays a regulatory role in the survival, growth and development, differentiation, regeneration and functional maintenance of neurons. They act not only on catecholaminergic neurons in the peripheral nervous system, but also on cholinergic neurons in the brain. Alzheimer's disease is thought to be associated with degeneration and shedding of cholinergic neurons. Researchers have tried giving NGFs in the brain to treat Alzheimer's disease. Because NGF is a large protein with a molecular weight of up to 12,000 and cannot pass through the blood-brain barrier, this treatment method cannot be applied to humans. Therefore, researchers have been working to find NGF-like substances ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C49/753C07C45/64C07C49/713C07C45/65C07C281/12C07C311/49C07C303/40C07D309/12
CPCC07C45/64C07C45/65C07C281/12C07C303/40C07D309/12C07C49/753C07C49/713C07C311/49
Inventor 张健蒋德辉沈校军
Owner TAIHO PHARMA CO LTD
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