JP2008013506A - Method for producing furan derivative - Google Patents
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Abstract
Description
本発明は、新規なフラン誘導体の製造方法に関する。 The present invention relates to a method for producing a novel furan derivative.
フラン誘導体は、天然物、医薬品、香料などの生理活性物質に多くみられる有用な化合物群である。したがって、このようなフラン誘導体を簡便に合成することが重要である。 Furan derivatives are a group of useful compounds often found in physiologically active substances such as natural products, pharmaceuticals, and fragrances. Therefore, it is important to easily synthesize such furan derivatives.
しかし、従来のフラン誘導体の合成は、100℃で反応させるなどの強い条件を用いる(例えば特許文献1参照)、あるいは工程数が多い条件で行う必要がある。
すなわち、本発明は、上記問題に鑑みなされたものであり、その目的は、温和な条件で簡便にフラン誘導体を製造する方法を提供することにある。 That is, the present invention has been made in view of the above problems, and an object thereof is to provide a method for easily producing a furan derivative under mild conditions.
本発明者らは、上記課題を解決すべく、鋭意検討した結果、パラジウム触媒を用いて、フラン誘導体を製造すると、上記課題を解決できることを見出した。すなわち、本発明は、以下のとおりである。 As a result of intensive studies to solve the above problems, the present inventors have found that the above problems can be solved by producing a furan derivative using a palladium catalyst. That is, the present invention is as follows.
本発明のフラン誘導体の製造方法は、対称性メソ化合物と、β−ケトエステルまたはβ−ケトアミドとを、パラジウム触媒下で、反応させ、フラン誘導体を製造するものである。 In the method for producing a furan derivative of the present invention, a furan derivative is produced by reacting a symmetrical meso compound with a β-ketoester or β-ketoamide in the presence of a palladium catalyst.
前記対称性メソ化合物は、一般式(I)で表される化合物または一般式(II)で表される化合物であればよい。
式中、R1は、メチル基、エチル基などのアルキル基、フェニル基などを示す。
式中、R1は、アセチル基、ベンゾイル基などを示す。
The symmetrical meso compound may be a compound represented by general formula (I) or a compound represented by general formula (II).
In the formula, R 1 represents an alkyl group such as a methyl group or an ethyl group, a phenyl group, or the like.
In the formula, R 1 represents an acetyl group, a benzoyl group, or the like.
前記β−ケトエステル、β−ケトアミド、または1,3−ジケトンは、一般式(III)、一般式(IV)で表される化合物、または一般式(V)で表される化合物であればよい。
式中、R3は、メチル基、エチル基、プロピル基、デシル基などの炭素数1〜12の置換基を有していてもよいアルキル基、2−ヒドロキシ−2−フェニルエチル基、4−メチル−3−ペンテニル基、4,9−ジメチル−3,7−ペンタジエニル基などの炭素数2〜12の置換基を有していてもよいアルケニル基、ブタ−3−イン−1−イル基などの炭素数2〜12の置換基を有していてもよいアルキニル基、フェニル基などを示し、R4は、メチル基を示す。
式中、R5、R6は、同一または異なっていてもよい水素原子、メチル基、エチル基、プロピル基、デシル基などの炭素数1〜12の置換基を有していてもよいアルキル基、エチレン基、プロペン基、3−メチルプロペン基、4−メチル−3−ペンテニル基、4,9−ジメチル−3,7−ペンタジエニル基などの炭素数2〜12の置換基を有していてもよいアルケニル基を示す。また、R5とR6は、結合して環を形成していてもよい。
The β-ketoester, β-ketoamide, or 1,3-diketone may be a compound represented by general formula (III), general formula (IV), or a compound represented by general formula (V).
In the formula, R 3 represents an alkyl group which may have a substituent having 1 to 12 carbon atoms such as a methyl group, an ethyl group, a propyl group or a decyl group, a 2-hydroxy-2-phenylethyl group, 4- Alkenyl groups optionally having 2 to 12 carbon atoms such as methyl-3-pentenyl group and 4,9-dimethyl-3,7-pentadienyl group, but-3-yn-1-yl group, etc. An alkynyl group or a phenyl group which may have a substituent having 2 to 12 carbon atoms, and R 4 represents a methyl group.
In formula, R < 5 >, R < 6 > is the alkyl group which may have C1-C12 substituents, such as a hydrogen atom, a methyl group, an ethyl group, a propyl group, a decyl group, which may be the same or different. , Ethylene groups, propene groups, 3-methylpropene groups, 4-methyl-3-pentenyl groups, 4,9-dimethyl-3,7-pentadienyl groups and the like, Good alkenyl group. R 5 and R 6 may combine to form a ring.
本発明は、パラジウム触媒を用いることで、温和な条件で簡便にフラン誘導体を製造する方法を提供することができる。 The present invention can provide a method for easily producing a furan derivative under mild conditions by using a palladium catalyst.
以下に、本発明を詳細に説明する。 The present invention is described in detail below.
[対称性メソ化合物]
本発明で用いる対称性メソ化合物としては、例えば、下記化学式(I)で表されるシス−2−ブテン−1,4−ジオールのジカルボナート体、下記化学式(II)で表されるシクロペンタエン、シクロヘキサエンのジカルボナート体、ジエステル体が挙げられる。
式中、R1は、メチル基、エチル基などのアルキル基、フェニル基などを示す。
式中、R2は、アセチル基、ベンゾイル基などを示す。
[Symmetrical meso compounds]
Examples of the symmetric meso compound used in the present invention include a dicarbonate of cis-2-butene-1,4-diol represented by the following chemical formula (I), cyclopentaene represented by the following chemical formula (II), Examples include dicarbonate and diester of cyclohexaene.
In the formula, R 1 represents an alkyl group such as a methyl group or an ethyl group, a phenyl group, or the like.
In the formula, R 2 represents an acetyl group, a benzoyl group, or the like.
[β−ケトエステル]
本発明に用いるβ−ケトエステルとしては、一般式(III)で表されるケトプロパン酸を基本構造に有する化合物である。
式中、R3は、メチル基、エチル基、プロピル基、デシル基などの炭素数1〜12の置換基を有していてもよいアルキル基、2−ヒドロキシ−2−フェニルエチル基、4−メチル−3−ペンテニル基、4,9−ジメチル−3,7−ペンタジエニル基などの炭素数2〜12の置換基を有していてもよいアルケニル基、ブタ−3−イン−1−イル基などの炭素数2〜12の置換基を有していてもよいアルキニル基、フェニル基などを示し、R4は、メチル基を示す。
[Β-ketoester]
The β-ketoester used in the present invention is a compound having ketopropanoic acid represented by the general formula (III) in the basic structure.
In the formula, R 3 represents an alkyl group which may have a substituent having 1 to 12 carbon atoms such as a methyl group, an ethyl group, a propyl group or a decyl group, a 2-hydroxy-2-phenylethyl group, 4- Alkenyl groups optionally having 2 to 12 carbon atoms such as methyl-3-pentenyl group and 4,9-dimethyl-3,7-pentadienyl group, but-3-yn-1-yl group, etc. An alkynyl group or a phenyl group which may have a substituent having 2 to 12 carbon atoms, and R 4 represents a methyl group.
[ケトアミド]
本発明に用いるケトアミドとしては、一般式(IV)で表される化合物が挙げられる。
As ketoamide used for this invention, the compound represented by general formula (IV) is mentioned.
[1,3−ジケトン]
本発明に用いる1,3−ジケトンとしては、一般式(V)で表される化合物が挙げられる。
式中、R5、R6は、同一または異なっていてもよい水素原子、メチル基、エチル基、プロピル基、デシル基などの炭素数1〜12の置換基を有していてもよいアルキル基、エチレン基、プロペン基、3−メチルプロペン基、4−メチル−3−ペンテニル基、4,9−ジメチル−3,7−ペンタジエニル基などの炭素数2〜12の置換基を有していてもよいアルケニル基を示す。また、R5とR6は、結合して環を形成していてもよい。
[1,3-diketone]
Examples of the 1,3-diketone used in the present invention include compounds represented by the general formula (V).
In formula, R < 5 >, R < 6 > is the alkyl group which may have C1-C12 substituents, such as a hydrogen atom, a methyl group, an ethyl group, a propyl group, a decyl group, which may be the same or different. , Ethylene groups, propene groups, 3-methylpropene groups, 4-methyl-3-pentenyl groups, 4,9-dimethyl-3,7-pentadienyl groups and the like, Good alkenyl group. R 5 and R 6 may combine to form a ring.
1,3−ジケトンの具体例としては、1,3−シクロヘキサンジオン、5,5−ジメチル−1,3−シクロヘキサンジオンなどがあげられる。 Specific examples of 1,3-diketones include 1,3-cyclohexanedione and 5,5-dimethyl-1,3-cyclohexanedione.
[パラジウム触媒]
本発明のフラン誘導体の製造方法に用いるパラジウム触媒としては、例えば、[Pd(η3−C3H5)Cl]2、Pd(OAc)2、Pd2dba3・CHCl3、Pd(PPh3)4などを用いることができる。
[Palladium catalyst]
Examples of the palladium catalyst used in the method for producing a furan derivative of the present invention include [Pd (η 3 -C 3 H 5 ) Cl] 2 , Pd (OAc) 2 , Pd 2 dba 3 .CHCl 3 , Pd (PPh 3 4 ) or the like can be used.
[その他の成分]
本発明の製造方法において、例えばジフェニルホスフィノフェロセン(DPPF)の存在下、さらに炭酸カリウム、トリフェニルホスフィン、第三級アミン(トリエチルアミン、1,8−ジアザビシクロ[5.4.0]−7−ウンデセン(DBU))などの有機または無機塩の存在下で反応を行ってもよい。DPPFの存在下で反応を行う場合には、反応系に2.5モル%添加する。
[Other ingredients]
In the production method of the present invention, for example, in the presence of diphenylphosphinoferrocene (DPPF), further potassium carbonate, triphenylphosphine, tertiary amine (triethylamine, 1,8-diazabicyclo [5.4.0] -7-undecene. The reaction may be carried out in the presence of an organic or inorganic salt such as (DBU)). When the reaction is performed in the presence of DPPF, 2.5 mol% is added to the reaction system.
[溶媒]
本発明の方法を実施するにあたり、用いる溶媒は特に制限はされないが、好ましくは不活性溶媒下に実施される。具体的に本発明の製造方法で用いる溶媒としては、テトラヒドロフラン(THF)、ジクロロメタン、ジメチルスルホキシド(DMSO)、アセトニトリル、ジクロロエタンなどの公知の有機溶媒が挙げられる。
[solvent]
In carrying out the method of the present invention, the solvent used is not particularly limited, but it is preferably carried out in an inert solvent. Specific examples of the solvent used in the production method of the present invention include known organic solvents such as tetrahydrofuran (THF), dichloromethane, dimethyl sulfoxide (DMSO), acetonitrile, dichloroethane and the like.
[反応]
本反応は、常圧下、窒素、アルゴン等の不活性ガス雰囲気下に実施されるが、加圧条件下に実施することもできる。反応温度は20℃〜60℃の範囲で実施される反応時間は、反応条件、対称性メソ化合物と、β−ケトエステル、β−ケトアミド、および1,3−ジケトン、及びパラジウム触媒等により異なるが、1〜35時間の範囲から選択すればよい。反応終了後、シリカゲルを用いて濾過した後、得られた濾液を濃縮する。濃縮残渣を、ヘキサン・酢酸エチル混液などを展開溶媒として用いて、シリカゲル分取薄層クロマトグラフィー、カラムクロマトグラフィーにより目的物を分取する。展開溶媒の種類、混合比などは、得られるフラン誘導体により異なる。また、薄層クロマトグラフの回数は、1回に限らず、複数回行ってもよい。
[reaction]
This reaction is performed under normal pressure and an inert gas atmosphere such as nitrogen and argon, but can also be performed under pressurized conditions. The reaction temperature is 20 to 60 ° C. The reaction time varies depending on the reaction conditions, the symmetric meso compound, the β-ketoester, β-ketoamide, 1,3-diketone, palladium catalyst, and the like. What is necessary is just to select from the range of 1-35 hours. After completion of the reaction, the mixture is filtered using silica gel, and the obtained filtrate is concentrated. From the concentrated residue, the target product is fractionated by silica gel preparative thin layer chromatography or column chromatography using a mixed solution of hexane / ethyl acetate or the like as a developing solvent. The kind of developing solvent, the mixing ratio, and the like vary depending on the furan derivative obtained. Further, the number of thin-layer chromatographs is not limited to one, and may be performed a plurality of times.
本発明における反応は、以下のように進行する。
本発明の方法を用いてフラン誘導体を製造すると、温和な条件で簡便にフラン誘導体を製造することができる。 When a furan derivative is produced using the method of the present invention, the furan derivative can be easily produced under mild conditions.
以下、実施例により本発明を説明するが、本発明はかかる実施例に限定されるものではない。 EXAMPLES Hereinafter, although an Example demonstrates this invention, this invention is not limited to this Example.
[実施例1]
ジアセタート(39.8mg、0.20mmol)、ケトエステル(38.6mg、0.21mmol)、[Pd(η3−C3H5)Cl]2(1.0mg、0.0027mmol)、DPPF(3.8mg、0.0068mmol)、DBU(61mg、0.40mmol)をTHF1mlに溶解した液を、窒素置換し、50℃で一晩攪拌しながら反応させた。得られた反応生成物を含む混合液をシリカゲル(BW−200、富士シリアル化学(株)製)を用いて濾過した。濾液は、減圧下で、濃縮した。残渣を、ヘキサン・酢酸エチル混液(10:1(体積比))を用いてシリカゲル分取TLCで分離し、所望のフラン誘導体を28mg(収量:53%)を得た。得られたフラン誘導体は、油状物であった(Rf=0.59)
FAB−MS m/z(%):307(M+,27);1H−NMR δ(CDCl3):1.16−1.26(1H,m),1.61(3H,s),1.67(3H,s),1.82−1.94(1H,m),2.01−2.14(2H,m),2.24(2H,dd,J=7.6,15.1Hz),2.57−2.73(2H,m),2.96−3.03(1H,m),3.72(3H,s),4.66−4.72(1H,m),5.09−6.16(1H,m),5.92−5.98(1H,m),6.16−6.22(1H,m).
Diacetate (39.8 mg, 0.20 mmol), ketoester (38.6 mg, 0.21 mmol), [Pd (η 3 -C 3 H 5 ) Cl] 2 (1.0 mg, 0.0027 mmol), DPPF (3. A solution prepared by dissolving 8 mg, 0.0068 mmol) and DBU (61 mg, 0.40 mmol) in 1 ml of THF was purged with nitrogen and reacted at 50 ° C. with stirring overnight. The resulting mixture containing the reaction product was filtered using silica gel (BW-200, manufactured by Fuji Serial Chemical Co., Ltd.). The filtrate was concentrated under reduced pressure. The residue was separated by silica gel preparative TLC using a mixed solution of hexane / ethyl acetate (10: 1 (volume ratio)) to obtain 28 mg (yield: 53%) of the desired furan derivative. The furan derivative obtained was an oil (Rf = 0.59).
FAB-MS m / z (%): 307 (M + , 27); 1 H-NMR δ (CDCl 3 ): 1.16 to 1.26 (1H, m), 1.61 (3H, s), 1.67 (3H, s), 1.82-1.94 (1H, m), 2.01-2.14 (2H, m), 2.24 (2H, dd, J = 7.6, 15 .1Hz), 2.57-2.73 (2H, m), 2.96-3.03 (1H, m), 3.72 (3H, s), 4.66-4.72 (1H, m ), 5.09-6.16 (1H, m), 5.92-5.98 (1H, m), 6.16-6.22 (1H, m).
[実施例2]
下式に示すジアセタートを用いて、表1に示すようにβ−ケトエステルの種類を変えて、実施例1と同様にして、フラン誘導体を作成した。得られたフラン誘導体とその収量を表1に示す。
Using a diacetate represented by the following formula, a furan derivative was prepared in the same manner as in Example 1 except that the type of β-ketoester was changed as shown in Table 1. Table 1 shows the furan derivatives obtained and their yields.
[実施例3]
下式に示すジアセタートを用いて、ケトエステルの種類を変えて、実施例1と同様にして、フラン誘導体を作成した。得られたフラン誘導体とその収量を表1に示す。ケトエステルの種類を変えることで、光学活性を有するフラン誘導体が得られた。
A furan derivative was prepared in the same manner as in Example 1 except that the type of ketoester was changed using diacetate represented by the following formula. Table 1 shows the furan derivatives obtained and their yields. A furan derivative having optical activity was obtained by changing the type of ketoester.
[実施例4]
下式に示すジアセタートとケトエステルとを用いて、トリエチルアミンを塩として用い、溶媒をジクロロメタンに変えて、室温で6時間反応させて、実施例1と同様に、フラン誘導体を作成した。得られたフラン誘導体の収量は、52%であった。
A furan derivative was prepared in the same manner as in Example 1 by using diacetate and ketoester represented by the following formula, using triethylamine as a salt, changing the solvent to dichloromethane and reacting at room temperature for 6 hours. The yield of the obtained furan derivative was 52%.
[実施例5]
下式に示すジアセタートとケトエステルとを用いて、溶媒の種類、反応時間、反応温度、延期の種類を変えて、実施例1と同様にして、フラン誘導体を作成した。得られたフラン誘導体とその収量を表2に示す。
A furan derivative was prepared in the same manner as in Example 1 except that the type of solvent, reaction time, reaction temperature, and type of postponement were changed using diacetate and ketoester represented by the following formula. Table 2 shows the furan derivatives obtained and their yields.
[実施例6]
下式に示すジカルボナート(16.5mg、0.081mmol)、ケトアミド(19.4mg、0.095mmol)、[Pd(η3−C3H5)Cl]2(1mg、0.0027mmol)、DPPF(3.8mg、0.0068mmol)、炭酸カリウム(22mg、0.16mmol)をアセトニトリル1mlに溶解した液を、窒素置換し、50℃で一晩攪拌しながら反応させた。得られた反応生成物を含む混合液をシリカゲル(BW−200、富士シリアル化学(株)製)を用いて濾過した。濾液は、減圧下で、濃縮した。残渣を、ヘキサン・酢酸エチル混液(3:1(体積比))を用いてシリカゲル分取TLCで2回分離し、所望のフラン誘導体として低極性体2.2mg(収量:11%)、高極性体2.9mg(収量:14%)を得た。低極性体:Rf=0.57、高極性体:Rf=0.49
Dicarbonate (16.5 mg, 0.081 mmol), ketoamide (19.4 mg, 0.095 mmol), [Pd (η 3 -C 3 H 5 ) Cl] 2 (1 mg, 0.0027 mmol), DPPF ( A solution prepared by dissolving 3.8 mg, 0.0068 mmol) and potassium carbonate (22 mg, 0.16 mmol) in 1 ml of acetonitrile was purged with nitrogen and reacted at 50 ° C. with stirring overnight. The resulting mixture containing the reaction product was filtered using silica gel (BW-200, manufactured by Fuji Serial Chemical Co., Ltd.). The filtrate was concentrated under reduced pressure. The residue was separated twice by silica gel preparative TLC using a mixed solution of hexane / ethyl acetate (3: 1 (volume ratio)), and 2.2 mg (yield: 11%) of a low polar substance as a desired furan derivative was obtained. 2.9 mg (yield: 14%) of the product was obtained. Low polarity body: Rf = 0.57, High polarity body: Rf = 0.49
[実施例7]
下式に示すジアセタートと1,3−ジケトンを用いて、塩としてトリフェニルホスフィンと炭酸カリウムとを用いて、室温で2.5時間反応させた以外は、実施例1と同様にして、フラン誘導体を作成した。得られたフラン誘導体とその収量を下式に示す。
[Example 7]
A furan derivative was prepared in the same manner as in Example 1 except that diacetate represented by the following formula and 1,3-diketone were used and reacted at room temperature for 2.5 hours using triphenylphosphine and potassium carbonate as salts. It was created. The obtained furan derivative and its yield are shown in the following formula.
Claims (3)
式中、R1は、メチル基、エチル基などのアルキル基、フェニル基などを示す。
式中、R2は、アセチル基、ベンゾイル基などを示す。 The method for producing a furan derivative according to claim 1, wherein the symmetric meso compound is a compound represented by the general formula (I) or a compound represented by the general formula (II).
In the formula, R 1 represents an alkyl group such as a methyl group or an ethyl group, a phenyl group, or the like.
In the formula, R 2 represents an acetyl group, a benzoyl group, or the like.
式中、R3は、メチル基、エチル基、プロピル基、デシル基などの炭素数1〜12の置換基を有していてもよいアルキル基、2−ヒドロキシ−2−フェニルエチル基、4−メチル−3−ペンテニル基、4,9−ジメチル−3,7−ペンタジエニル基などの炭素数2〜12の置換基を有していてもよいアルケニル基、ブタ−3−イン−1−イル基などの炭素数2〜12の置換基を有していてもよいアルキニル基、フェニル基などを示し、R4は、メチル基を示す。
式中、R5、R6は、同一または異なっていてもよい水素原子、メチル基、エチル基、プロピル基、デシル基などの炭素数1〜12の置換基を有していてもよいアルキル基、エチレン基、プロペン基、3−メチルプロペン基、4−メチル−3−ペンテニル基、4,9−ジメチル−3,7−ペンタジエニル基などの炭素数2〜12の置換基を有していてもよいアルケニル基を示す。また、R5とR6は、結合して環を形成していてもよい。
The β-ketoester, β-ketoamide, or 1,3-diketone is a compound represented by general formula (III), general formula (IV), or a compound represented by general formula (V). A method for producing the furan derivative according to 1.
In the formula, R 3 represents an alkyl group which may have a substituent having 1 to 12 carbon atoms such as a methyl group, an ethyl group, a propyl group or a decyl group, a 2-hydroxy-2-phenylethyl group, 4- Alkenyl groups optionally having 2 to 12 carbon atoms such as methyl-3-pentenyl group and 4,9-dimethyl-3,7-pentadienyl group, but-3-yn-1-yl group, etc. An alkynyl group or a phenyl group which may have a substituent having 2 to 12 carbon atoms, and R 4 represents a methyl group.
In formula, R < 5 >, R < 6 > is the alkyl group which may have C1-C12 substituents, such as a hydrogen atom, a methyl group, an ethyl group, a propyl group, a decyl group, which may be the same or different. , Ethylene groups, propene groups, 3-methylpropene groups, 4-methyl-3-pentenyl groups, 4,9-dimethyl-3,7-pentadienyl groups and the like, Good alkenyl group. R 5 and R 6 may combine to form a ring.
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
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EP2254891A2 (en) * | 2008-03-03 | 2010-12-01 | Senomyx, Inc. | Isosorbide derivatives and their use as flavor modifiers, tastants, and taste enhancers |
CN106854191A (en) * | 2015-12-08 | 2017-06-16 | 中国科学院大连化学物理研究所 | The 2- synthetic method of the 3- methylene-DHF containing chiral quaternary carbon center |
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Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2254891A2 (en) * | 2008-03-03 | 2010-12-01 | Senomyx, Inc. | Isosorbide derivatives and their use as flavor modifiers, tastants, and taste enhancers |
CN102083836A (en) * | 2008-03-03 | 2011-06-01 | 西诺米克斯公司 | Isosorbide derivatives and their use as flavor modifiers, tastants, and taste enhancers |
EP2254891A4 (en) * | 2008-03-03 | 2011-07-27 | Senomyx Inc | Isosorbide derivatives and their use as flavor modifiers, tastants, and taste enhancers |
US8420145B2 (en) | 2008-03-03 | 2013-04-16 | Senomyx, Inc. | Isosorbide derivatives and their use as flavor modifiers, tastants, and taste enhancers |
CN106854191A (en) * | 2015-12-08 | 2017-06-16 | 中国科学院大连化学物理研究所 | The 2- synthetic method of the 3- methylene-DHF containing chiral quaternary carbon center |
CN106854191B (en) * | 2015-12-08 | 2019-09-27 | 中国科学院大连化学物理研究所 | 2- 3- methylene -2,3-dihydrofuran synthetic methods containing chiral quaternary carbon center |
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