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Preparation method of high-purity cyclohexenone long-chain alcohol

A technology of cyclohexenone long-chain alcohol and cyclohexenone, which is applied in the field of medicinal chemistry and synthetic chemistry, and can solve the problems of high cost, large loss and low melting point of column chromatography

Active Publication Date: 2017-08-11
TAIHO PHARMA CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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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  • Preparation method of high-purity cyclohexenone long-chain alcohol
  • Preparation method of high-purity cyclohexenone long-chain alcohol
  • Preparation method of high-purity cyclohexenone long-chain alcohol

Examples

Experimental program
Comparison scheme
Effect test

preparation example 13

[0085] Preparation 13-isobutoxy-2,6,6-trimethylcyclohex-2-en-1-one

[0086]

[0087] 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 to reflux to separate water for 16h. Post-treatment, cooled to ambient temperature, washed successively with 5% sodium hydroxide (80mL), water (80mL) and saturated brine (80mL), dried over anhydrous sodium sulfate, 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).

[0088] Preparation 23-Cyclohexylmethoxy-2,6,6-trimethylcyclohex-2-en-1-one

[0089]

[0090] 2,4,4-trimethylcyclohexyl-1,3-dione VII (10g, 1eq) and cyclohexanemethanol (14.8g, 2eq) were added to cyclohexane (100mL), and p-TSA· H2O (0.62g, 0.05eq), heated to reflux to sep...

preparation example 43-

[0094] Preparation 43-Methoxy-2,6,6-trimethylcyclohex-2-en-1-one

[0095]

[0096] 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 (167mg, 0.05eq), stirred overnight at room temperature. After treatment, add dichloromethane (30mL) to dilute, wash with 5% sodium hydroxide (20mL), water (10mL) and saturated brine (10mL) successively, dry over anhydrous sodium sulfate, concentrate to dryness, and perform column purification to obtain 3 - Methoxy-2,6,6-trimethylcyclohex-2-en-1-one (2.19 g, 74.4%). 1 H NMR (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).

[0097] Preparation 53,3'-(Propyl-1,2-dioxo)-bis(2,6,6-trimethylcyclohexyl-2-en-1-one)

[0098]

[0099] 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 (30mL) was added to the flask, heated to reflux to se...

preparation example 93-(1

[0110] Preparation 9 3-(15-chloropentadecyloxy)-2,6,6-trimethylcyclohexyl-2-en-1-one

[0111]

[0112] 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 to reflux to separate water for 16h, post-treatment, cool to ambient temperature, successively wash with 5% sodium hydroxide (20mL), water (10mL) and saturated saline ( 10mL) was washed, dried over anhydrous sodium sulfate, and concentrated to dryness to obtain 3-(15-chloropentadecyloxy)-2,6,6-trimethylcyclohexyl-2-en-1-one (2.46g, 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 shown in formula I. The compound shown in the formula I is prepared with a metal mediated Barbier reaction. The method has the advantages that the route is short, the yield and product purity are high, and the method is suitable for industrial expanding.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry and synthetic chemistry, and in particular relates to a preparation method of high-purity cyclohexenone long-chain alcohol. Background technique [0002] Nerve growth factor (NGF for short), mainly present in the hippocampus and cerebral cortex, regulates the survival, growth and development, differentiation, regeneration and function 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 the degeneration and loss of cholinergic neurons. Researchers have tried to administer NGFs in the brain to treat Alzheimer's disease. Since NGF is a macromolecular protein with a molecular weight of up to 12,000, it cannot penetrate the blood-brain barrier, so this treatment method cannot be applied to humans. Therefore, researchers have been working on finding ...

Claims

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Application Information

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Patent Type & Authority Applications(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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