JP2890755B2 - Cyclic host compound - Google Patents
Cyclic host compoundInfo
- Publication number
- JP2890755B2 JP2890755B2 JP23270290A JP23270290A JP2890755B2 JP 2890755 B2 JP2890755 B2 JP 2890755B2 JP 23270290 A JP23270290 A JP 23270290A JP 23270290 A JP23270290 A JP 23270290A JP 2890755 B2 JP2890755 B2 JP 2890755B2
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- JP
- Japan
- Prior art keywords
- host compound
- cyclic
- cyclic host
- group
- present
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】 〔産業上の利用分野〕 本発明は、環状の新規なホスト化合物に関するもので
あり、詳細にはゲスト−ホスト効果を利用して、包接さ
れるゲスト分子の分析等に有用な環状ホスト化合物に関
するものである。TECHNICAL FIELD The present invention relates to a novel cyclic host compound, and more specifically, utilizing the guest-host effect, analysis of guest molecules to be clathrated, etc. The present invention relates to a cyclic host compound useful in.
下記一般式〔II〕 （式中R1、R2、R3、R4、およびR5は水素原子、ハロゲン
原子、低級アルキル基、ニトロ基またはアルコキシ基を
示し、ｎは1,2または３の数を示す）で表わされるアゾ
フェノール誘導体は、金属イオンに対して錯形成能を有
するが、その吸収波長は錯化する金属イオンにより異な
るため、金属イオンの分析に有用なことが知られている
（特公平１−50230号公報参照）。The following general formula [II] (Wherein R 1 , R 2 , R 3 , R 4 , and R 5 represent a hydrogen atom, a halogen atom, a lower alkyl group, a nitro group or an alkoxy group, and n represents a number of 1, 2 or 3). The azophenol derivative represented has a complex-forming ability with respect to metal ions, but its absorption wavelength is known to be useful for the analysis of metal ions because it depends on the complexing metal ion (Japanese Patent Publication No. 50230).
本発明は、環状フェノール性化合物に特殊な基を導入
することにより、金属イオンの錯形成能、イオン選択性
等が従来のものとは異なる新しい性質を有する化合物を
提供することを目的とするものである。An object of the present invention is to provide a compound having novel properties such as metal ion complexing ability and ion selectivity which are different from conventional ones by introducing a special group into a cyclic phenolic compound. Is.
すなわち、本発明は下記一般式〔Ｉ〕 （式中、R1は水素原子または低級アルキル基を示し、
R2、R3はそれぞれ独立して低級アルキル基を示す。）で
表わされる環状ホスト化合物に関する。That is, the present invention has the following general formula [I] (In the formula, R 1 represents a hydrogen atom or a lower alkyl group,
R 2 and R 3 each independently represent a lower alkyl group. ) Relates to a cyclic host compound.
以下本発明を説明するに、本発明の環状ホスト化合物
は、前記一般式〔Ｉ〕で表されるものである。式中、R1
は水素原子又はメチル基、エチル基、プロピル基、ブチ
ル基等の低級アルキル基を示し、R2およびR3はそれぞれ
独立してメチル基、エチル基、プロピル基、ブチル基等
の低級アルキル基を示す。The cyclic host compound of the present invention is represented by the above general formula [I]. Where R 1
Represents a hydrogen atom or a lower alkyl group such as a methyl group, an ethyl group, a propyl group or a butyl group, and R 2 and R 3 each independently represent a lower alkyl group such as a methyl group, an ethyl group, a propyl group or a butyl group. Show.
本発明の環状ホスト化合物は、例えば下記構造式〔II
I〕 で表わされる環状フェノール性化合物と炭酸水素ナトリ
ウム、水酸化ナトリウム、水酸化カリウム等のアルカリ
を水又はメタノール、エタノール等のアルコール、アセ
トン等のケトン等の親水性溶媒に溶解させ、下記一般式
〔IV〕 （式中、R1、R2、R3は前記定義に同じ。）で示される化
合物の塩酸塩または硫酸塩の水溶液を加えて混合液と
し、これに低温、好ましくは０〜５℃にてフェリシアン
化カリウム、次亜塩素酸ナトリウム、過硫酸アンモニウ
ム等の酸化剤の水溶液を加えて５分〜５時間反応させ、
生成した沈殿を濾別することにより容易に得ることがで
きる。さらに必要に応じて、カラムクロマトグラフィ
ー、再結晶等による精製を行なってもよい。The cyclic host compound of the present invention has, for example, the following structural formula [II
I] A cyclic phenolic compound represented by sodium hydrogen carbonate, sodium hydroxide, an alkali such as potassium hydroxide is dissolved in a hydrophilic solvent such as water or an alcohol such as methanol or ethanol, a ketone such as acetone, the following general formula [IV ] (In the formula, R 1 , R 2 and R 3 are the same as defined above.) An aqueous solution of a hydrochloride or a sulfate of the compound is added to form a mixed solution, and this is mixed at low temperature, preferably 0 to 5° C. Add an aqueous solution of an oxidizing agent such as potassium ferricyanide, sodium hypochlorite, ammonium persulfate and react for 5 minutes to 5 hours,
It can be easily obtained by filtering the formed precipitate. Further, if necessary, purification by column chromatography, recrystallization or the like may be performed.
かくして得られる本発明の環状ホスト化合物は、環状
フェノール骨格の中にキノン骨格を導入したために、ゲ
スト分子を選択的に取り込む。そのものの吸収スペクト
ルは包接されるゲスト分子により異なるので、それらゲ
スト分子の抽出、分離および分析に有用である。The thus obtained cyclic host compound of the present invention selectively incorporates the guest molecule because the quinone skeleton is introduced into the cyclic phenol skeleton. Since its absorption spectrum depends on the guest molecules to be included, it is useful for extraction, separation and analysis of those guest molecules.
以下に実施例を挙げて、本発明を更に具体的に説明す
るが、本発明はこれら実施例に限定されるものではな
い。Hereinafter, the present invention will be described more specifically with reference to Examples, but the present invention is not limited to these Examples.
実施例１ ＜合成法＞ 下記構造式 で表わされるカリックス〔４〕アレーン300mg（0.707m
mol）および水酸化ナトリウム339mg（8.484m mol）をア
セトン100ml中に溶解させた。このアセトン溶液に下記
構造式 で表わされる化合物の塩酸塩1.218g（5.656m mol）の飽
和水溶液を加え、これにフェリシアン化カリウムK3Fe
（CN）61.864g（5.656m mol）を溶かした水溶液をゆっ
くりと滴下し、その後10分間撹拌した。次いで、反応溶
液を200mlの水中に注ぎ、酢酸によって中和した。アセ
トンを留去したのち、沈殿を濾取し、水洗した。乾燥
後、シリカゲルカラムクトマトグラフィー（展開溶媒ク
ロロホルム）にて分離・精製して下記構造式で示される
目的の茶かっ色の固体320gを得た。（収率75.6％） ＜物性値＞ 元素分析値 赤外スペクトルを図−１に示した。Example 1 <Synthesis method> The following structural formula Calix[4]arene 300mg (0.707m
mol) and 339 mg (8.484 mmol) of sodium hydroxide were dissolved in 100 ml of acetone. This acetone solution has the following structural formula A saturated aqueous solution of the hydrochloride of the compound represented by 1.218 g (5.656 mmol) was added, and potassium ferricyanide K 3 Fe was added to this.
An aqueous solution in which 1.864 g (5.656 mmol) of (CN) 6 was dissolved was slowly added dropwise, followed by stirring for 10 minutes. The reaction solution was then poured into 200 ml of water and neutralized with acetic acid. After the acetone was distilled off, the precipitate was collected by filtration and washed with water. After drying, the product was separated and purified by silica gel column chromatography (developing solvent chloroform) to obtain 320 g of the desired brown brown solid represented by the following structural formula. (Yield 75.6%) <Physical properties> Elemental analysis value The infrared spectrum is shown in Fig. 1.
本発明の環状ホスト化合物は、特定のゲスト分子を包
接することができるので、その特定分子の抽出、分離、
分析等に応用することが有用である。Since the cyclic host compound of the present invention can include a specific guest molecule, extraction of the specific molecule, separation,
It is useful to apply to analysis.
図−１は、実施例１で得られた環状ホスト化合物の赤外
線スペクトルのグラフを表わす。 図中、縦軸は透過率（％）を表わし、横軸は波数（c
m-1）を表わす。FIG. 1 shows a graph of infrared spectrum of the cyclic host compound obtained in Example 1. In the figure, the vertical axis represents the transmittance (%), and the horizontal axis represents the wave number (c
m -1 ).
Claims (1)
R2、R3はそれぞれ独立して低級アルキル基を示す。） で表わされる環状ホスト化合物。1. A general formula [I] (In the formula, R 1 represents a hydrogen atom or a lower alkyl group,
R 2 and R 3 each independently represent a lower alkyl group. ) A cyclic host compound represented by:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP23270290A JP2890755B2 (en) | 1990-09-03 | 1990-09-03 | Cyclic host compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP23270290A JP2890755B2 (en) | 1990-09-03 | 1990-09-03 | Cyclic host compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH04112861A JPH04112861A (en) | 1992-04-14 |
| JP2890755B2 true JP2890755B2 (en) | 1999-05-17 |
Family
ID=16943438
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP23270290A Expired - Fee Related JP2890755B2 (en) | 1990-09-03 | 1990-09-03 | Cyclic host compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2890755B2 (en) |
-
1990
- 1990-09-03 JP JP23270290A patent/JP2890755B2/en not_active Expired - Fee Related
Non-Patent Citations (1)
| Title |
|---|
| Ｃｈｅｍ．Ｌｅｔｔ．Ｖｏｌ．６，ｐ．９３１−９３４（１９８９） |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH04112861A (en) | 1992-04-14 |
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