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δ 3 Asymmetric Synthesis of -2-Hydroxybakuchiol and Its Analog Compounds

A technology of bakuchiol and compound, which is applied in the field of chemical synthesis to achieve the effect of reducing bone loss

Inactive Publication Date: 2016-09-07
FUDAN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Reagents and conditions:a)Ph3P=CHCO2Et,Toluene,Reflux;77.7%.b)tBuPh2SiCl,DMAP(=N,N-dimethylpyridin-4-amine),1H-imidazole,CH2Cl2;91.8%.c)DIBALH,CH2Cl2, -20oC,82.6%.d)Me(OEt)3,EtCOOH,Reflux;73.4%.e)Bu4NF,THF;83.7%.f)DIBALH,CH2Cl2,-20oC;82.4%.g)Ph3P=CHCO2Et,Toluene, Reflux;79%.h)IBX,DMSO;94.5%.i)CHI3,CrCl2,THF;78.6%.j)4-(tBuPh2SiO)-C6H4Br,BuLi / ZnCl2;[Pd(OAc)2] / PPh3,THF ;90.1%.k)MeMgI,THF;88.0%.k)Bu4NF,THF;77.8%.It is known that since Δ 3 Since -2-hydroxybakuchiol was reported, there has been no report on its asymmetric total synthesis

Method used

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  • δ <sup>3</sup> Asymmetric Synthesis of -2-Hydroxybakuchiol and Its Analog Compounds
  • δ <sup>3</sup> Asymmetric Synthesis of -2-Hydroxybakuchiol and Its Analog Compounds
  • δ <sup>3</sup> Asymmetric Synthesis of -2-Hydroxybakuchiol and Its Analog Compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025]

[0026] 1. Step 1

[0027]

[0028] Add tiqueric acid (40g, 0.4mol) into a 100ml dry reaction flask, add thionyl chloride (44ml, 0.6mol) dropwise in an ice-water bath, connect to an exhaust gas treatment device, and react under reflux for 5h. Cool to room temperature and connect to a distillation device, and distill at atmospheric pressure (142° C.) to obtain the product, 9.7 g of a colorless liquid, with a yield of 82%.

[0029] 2. Step 2

[0030]

[0031] Sodium iodide (30g, 0.2mol) and 200ml of acetone were added to a dry 500ml reaction flask, tert-butyl bromoacetate (14.6ml, 0.1mol) was added with stirring, and the reaction was refluxed for 4h under the protection of argon. Cool to room temperature, filter, concentrate the filtrate under reduced pressure, dissolve the residue with 200ml of water, extract with ethyl acetate (200ml×3), combine the organic phases, and then use 10% sodium thiosulfate (200ml) and saturated saline ( 200ml) was washed, dried ov...

Embodiment 2

[0145]

[0146] 1. step 1

[0147]

[0148] Add 4-bromoanisole (0.25ml, 2.0mmol) to a dry 100ml reaction flask, under argon protection, dissolve 5ml of anhydrous THF, cool to -78°C, then add n-BuLi (0.8ml, 2.0mmol), reacted for 30min, slowly added anhydrous THF solution (5ml) of anhydrous zinc chloride (300mg, 2.2mmmol), raised the temperature to room temperature, and reacted for 1h. Add palladium acetate (22mg, 0.1mmol) and triphenylphosphine (26mg, 0.1mmol) to another 25ml dry reaction flask, protect with argon, dissolve in 2ml anhydrous THF, react at room temperature for 30min, the reaction solution turns reddish brown, This reaction solution was added to the above organozinc reaction solution, and then compound 11 (320mg, 1.0mmol) in anhydrous THF solution (2ml) was added, and the reaction was stirred overnight at room temperature. Quench the reaction with 15ml of saturated ammonium chloride solution, separate the organic phase, extract the aqueous phase with ethyl...

Embodiment 3

[0165]

[0166] 1. step 1

[0167]

[0168] Add bromobenzene (0.21ml, 2.0mmol) to a dry 100ml reaction flask, under argon protection, dissolve in 5ml of anhydrous THF, cool to -78°C, then add n-BuLi (0.8ml, 2.0mmol) dropwise, After reacting for 30 minutes, anhydrous THF solution (5 ml) of anhydrous zinc chloride (300 mg, 2.2 mmmol) was slowly added, and the temperature was raised to room temperature for 1 hour of reaction. Add palladium acetate (22mg, 0.1mmol) and triphenylphosphine (26mg, 0.1mmol) to another 25ml dry reaction flask, protect with argon, dissolve in 2ml anhydrous THF, react at room temperature for 30min, the reaction solution turns reddish brown, This reaction solution was added to the above organozinc reaction solution, and then compound 11 (320mg, 1.0mmol) in anhydrous THF solution (2ml) was added, and the reaction was stirred overnight at room temperature. Quench the reaction with 15ml of saturated ammonium chloride solution, separate the organic pha...

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Abstract

The invention belongs to the field of chemical synthesis, provides a novel method for synthesizing delta3-2-hydroxybakuchiol and particularly relates to an asymmetric synthesis method for delta3-2-hydroxybakuchiol and analog compounds. The delta3-2-hydroxybakuchiol and the analog compounds, the general formula of which is (I), are synthesized by an asymmetric synthesis route. Problems in the prior art, that the content of the delta3-2-hydroxybakuchiol obtained by extraction and separation from plants is very low, an extraction rate is very low, the delta3-2-hydroxybakuchiol is prone to oxidative deterioration in extraction and separation processes, and the like, are overcome by the method. The method can provide sufficient samples for related pharmaceutical research, and provides good foundations for pharmaceutical research on antibiosis, infection resistance, oxidation resistance, pigment deposition resistance, reduction of bone loss, immunosuppression, liver damage, sedation and hypnosis, and the like. In the formula (I), R1 is selected from 4-hydroxy, 3-hydroxy, 2-hydroxy, hydrogen, 4-methyl, 4-methoxy, 4-trifluoromethyl, 3,4-[d][1,3]dioxole, and 3,4-phenyl; R2 is selected from methyl, ethyl, and butyl; and R3 is selected from vinyl, ethyl and cyclopropyl.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, in particular to a Δ 3 -Asymmetric synthesis of 2-hydroxybakuchiol and analog compounds. Background technique [0002] Natural product Δ 3 -2-Hydroxybakuchiol, also known as isobakuchiol, was extracted from the leaves of Psoralea corylifolia L by Chilean chemist Cecilia Labbé et al. in 1996 (Labbé, C.; Faini, F.;Coll,J.;Connolly,J.D.Phytochemistry1996,42,1299), the following year, the research team of SUKH DEV also extracted and isolated the compound from the seeds of Psoralea corylifolia L, and compared with known compounds The comparison of the spectral data of 1997, 74, 970 to determine its absolute configuration. Psoraleae extract has rich and diverse biological activities, mainly in antibacterial, anti-infection, anti-oxidation, anti-pigmentation, reducing bone loss, immunosuppression, and liver damage protection. Suna Kim (Lim, S.-H.; Ha, T.-Y.; Kim, S.-R.; Ahn, J.; Park, H.J.; Kim, S....

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C39/19C07C37/055C07C43/23C07C41/26C07C33/30C07C29/147C07C33/28C07C33/48C07D317/54
CPCC07B41/02C07B53/00C07B2200/07C07C29/147C07C33/28C07C33/30C07C33/483C07C37/055C07C39/19C07C41/26C07C43/23C07C51/60C07C67/307C07C67/31C07C67/313C07C67/343C07C2601/02C07D263/26C07D317/54C07F7/1804C07F7/188C07F7/1892C07C69/65C07C69/738C07C69/732C07C69/63C07C57/66C07C69/734C07C69/618
Inventor 雷新胜林国强许千千赵群
Owner FUDAN UNIV
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