JPH01146853A - 2,5-substituted-cyclohexane-1,4-dione and production thereof - Google Patents
2,5-substituted-cyclohexane-1,4-dione and production thereofInfo
- Publication number
- JPH01146853A JPH01146853A JP30679587A JP30679587A JPH01146853A JP H01146853 A JPH01146853 A JP H01146853A JP 30679587 A JP30679587 A JP 30679587A JP 30679587 A JP30679587 A JP 30679587A JP H01146853 A JPH01146853 A JP H01146853A
- Authority
- JP
- Japan
- Prior art keywords
- cyclohexanedione
- bis
- ethyl
- reaction
- pyrrolidine
- 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.)
- Pending
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims abstract description 24
- DCZFGQYXRKMVFG-UHFFFAOYSA-N cyclohexane-1,4-dione Chemical compound O=C1CCC(=O)CC1 DCZFGQYXRKMVFG-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 239000000126 substance Substances 0.000 claims description 4
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 abstract description 14
- 238000006243 chemical reaction Methods 0.000 abstract description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract description 12
- PCCVSPMFGIFTHU-UHFFFAOYSA-N tetracyanoquinodimethane Chemical class N#CC(C#N)=C1C=CC(=C(C#N)C#N)C=C1 PCCVSPMFGIFTHU-UHFFFAOYSA-N 0.000 abstract description 10
- 239000002904 solvent Substances 0.000 abstract description 7
- 239000002994 raw material Substances 0.000 abstract description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract description 4
- 150000002894 organic compounds Chemical class 0.000 abstract description 2
- 239000004065 semiconductor Substances 0.000 abstract description 2
- 150000002081 enamines Chemical class 0.000 abstract 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- OILAIQUEIWYQPH-UHFFFAOYSA-N cyclohexane-1,2-dione Chemical group O=C1CCCCC1=O OILAIQUEIWYQPH-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 2
- QEQOMQUKHGZXAX-UHFFFAOYSA-N 2-[2-(dicyanomethyl)phenyl]propanedinitrile Chemical compound N#CC(C#N)C1=CC=CC=C1C(C#N)C#N QEQOMQUKHGZXAX-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 description 1
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000012916 structural analysis Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
［産業上の利用分野］
本発明は、テトラシアノキノジメタン（ＴＣＮＱ）ＩＢ
ｓ導体類の原料として有用な新規化合物を提供する。[Detailed Description of the Invention] [Industrial Application Field] The present invention provides tetracyanoquinodimethane (TCNQ) IB
A novel compound useful as a raw material for s-conductors is provided.
［従来の技術］
７．７，８．８−テトラシアノキノジメタン（ＴＣＮＱ
）は融点２９３．５〜２９６℃の黄色結晶である。この
化合物は容易に１個の電子を受は入れて安定なアニオン
ラジカルを形成し、その誘導体は極めて小さい電気抵抗
を示す。この化合物はチオフェノール、メルカプト酢酸
、ヨウ化水素などで還元されてフェニレンジマロノニト
リルとなり、これをＮ−ブロモスクシンイミドで酸化す
ると再びＴＣＮＱに戻る。実用化されたＴＣＮＱの用途
としてケミカルコンデンサーがある。[Prior art] 7.7,8.8-tetracyanoquinodimethane (TCNQ
) is a yellow crystal with a melting point of 293.5-296°C. This compound easily accepts one electron to form a stable anion radical, and its derivatives exhibit extremely low electrical resistance. This compound is reduced with thiophenol, mercaptoacetic acid, hydrogen iodide, etc. to become phenylene dimalononitrile, which is oxidized with N-bromosuccinimide to return to TCNQ. Chemical capacitors are a practical application of TCNQ.
ＴＣＮＱの合成法としては、たとえばマロノニトリルと
１．４−シクロヘキサンジオンを縮合させて得られる１
、４−ビス−（ジシアノメチレン）シクロヘキサンをピ
リジン中でＮ−ブロモスクシンイミドあるいは臭素を用
いて酸化する方法が知られている。As a method for synthesizing TCNQ, for example, 1 obtained by condensing malononitrile and 1,4-cyclohexanedione is used.
, 4-bis-(dicyanomethylene)cyclohexane is oxidized in pyridine using N-bromosuccinimide or bromine.
［発明が解決しようとする問題点］
上記のようにＴＣＮＱは有機化合物でありながら導電性
を有するので、該化合物の他のルートによる合成法を見
出したり、該化合物に骨格が類似した導電性を有する化
合物を見出すことは、この種の有機導電性化合物の研究
、開発、さらには実用化の上で重要である。[Problems to be solved by the invention] As mentioned above, although TCNQ is an organic compound, it has conductivity. It is important to find compounds that have this kind of organic conductive compounds in terms of research, development, and further practical application.
本発明は、有機半導体としての用途が期待できるＴＣＮ
Ｑ誘導体の中間体として有用な新規化合物を提供するこ
とを目的とするものである。The present invention is directed to TCN, which can be expected to be used as an organic semiconductor.
The object of the present invention is to provide a novel compound useful as an intermediate for Q derivatives.
［問題点を解決するための手段］
本発明の化合物は、次の一般式で示される２、５−ビス
〔２−（ジアルキルカルバモイル）エチル）−１，４−
シクロヘキサンジオンであり、文献未載の新規化合物で
ある。[Means for Solving the Problems] The compound of the present invention is 2,5-bis[2-(dialkylcarbamoyl)ethyl)-1,4-
It is cyclohexanedione and is a new compound that has not been described in any literature.
〔ここでＲはアルキル基を示す〕
次に、上式で示される本発明の化合物の製造法について
述べる。[Here, R represents an alkyl group] Next, a method for producing the compound of the present invention represented by the above formula will be described.
本発明の化合物は、次の反応式に従って製造できる。The compound of the present invention can be produced according to the following reaction formula.
反応はまず１．４−シクロヘキサンジオンをピロリジン
にてエナミン化する。In the reaction, 1,4-cyclohexanedione is first enaminated with pyrrolidine.
溶媒としては、ベンゼン、トルエン、キシレン等が使用
可能である。Benzene, toluene, xylene, etc. can be used as the solvent.
反応温度は還流下が望ましく、また反応中に副生ずる水
を系外に除去しながら反応を進行させる。触媒は特に必
要ではないが、ｐ−）ルエンスルホン酸などが使用でき
る。The reaction temperature is preferably reflux, and the reaction is allowed to proceed while water by-produced during the reaction is removed from the system. Although a catalyst is not particularly necessary, p-)luenesulfonic acid and the like can be used.
反応系は、生成したジェナミンの酸化を防止する点で窒
素雰囲気下に保つのが有利である。It is advantageous to maintain the reaction system under a nitrogen atmosphere in order to prevent oxidation of the generated genamine.
ピロリジンの使用量は、ｌ、４−シクロヘキサンジオン
１モルに対して２〜４モルの範囲から選ばれる。The amount of pyrrolidine used is selected from the range of 2 to 4 moles per mole of 1,4-cyclohexanedione.
反応時間は、１〜３時間が適当である。A suitable reaction time is 1 to 3 hours.
続いて、反応生成液から溶媒及び残余のピロリジンを除
去した後、Ｎ、Ｎ−ジアルキルアクリルアミドを反応さ
せる。Subsequently, after removing the solvent and remaining pyrrolidine from the reaction product solution, N,N-dialkyl acrylamide is reacted.
溶媒としては、ジオキサン、Ｎ、Ｎ−ジメチルホルムア
ミド、エタノール、メタノール、アセトニトリルなどが
使用される。As the solvent, dioxane, N,N-dimethylformamide, ethanol, methanol, acetonitrile, etc. are used.
Ｎ、Ｎ−ジアルキルアクリルアミドは、１．４−シクロ
ヘキサンジオン１モル当たり２〜４モルの割合で用いら
れる。N,N-dialkyl acrylamide is used in a proportion of 2 to 4 moles per mole of 1,4-cyclohexanedione.
還流下で３〜２４時間程度反応を行い、その後１．４−
シクロヘキサンジオンに対して２モル当量程度の水を添
加して１〜２時間程度、還流下で加水分解反応を続行す
ると目的物が得られる。The reaction is carried out under reflux for about 3 to 24 hours, and then 1.4-
The desired product is obtained by adding about 2 molar equivalents of water to cyclohexanedione and continuing the hydrolysis reaction under reflux for about 1 to 2 hours.
反応後は、溶媒及び残余の原料を除去した後、クロロホ
ルム等の有機溶媒で目的物を抽出する。抽出液から溶媒
を留去し、必要に応じて常法に従って精製操作を行って
製品化する。After the reaction, the solvent and remaining raw materials are removed, and then the target product is extracted with an organic solvent such as chloroform. The solvent is distilled off from the extract, and if necessary, a purification operation is performed according to a conventional method to produce a product.
本発明で使用するＮ、Ｎ−ジアルキルアクリルアミドは
、一般式Ｃ１１，＝ ＣｌＩＣ０ＮＲ，で示され、アル
キル基としては、メチル基、エチル基、プロピル基、ブ
チル基、ヘキシル基等任意のものであってよい。The N,N-dialkylacrylamide used in the present invention is represented by the general formula C11,=ClIC0NR, and the alkyl group is any one such as a methyl group, ethyl group, propyl group, butyl group, or hexyl group. good.
［作 用］
かくして得られる化合物は、テトラシアノキノジメタン
誘導体等の原料として有用である。[Function] The compound thus obtained is useful as a raw material for tetracyanoquinodimethane derivatives and the like.
［実施例］ 以下、実例を挙げて本発明を更に具体的に説明する。[Example] Hereinafter, the present invention will be explained in more detail by giving examples.
実例１
１．４−シクロヘキサンジオン１１２９（１，０モル）
、ピロリジン２１３ｙ（３，０モル）、トルエン４５０
ｍ１を混合し、還流下で窒素ガスを系に導入しながら脱
水下に反応を行った。１．５時間反応後、系からトルエ
ン及び残余のピロリジンを除去し、ジオキサン４００ｍ
ｌ、 Ｎ。Example 1 1,4-cyclohexanedione 1129 (1,0 mol)
, pyrrolidine 213y (3.0 mol), toluene 450
ml was mixed and the reaction was carried out under reflux and dehydration while introducing nitrogen gas into the system. After reacting for 1.5 hours, toluene and remaining pyrrolidine were removed from the system, and 400ml of dioxane was added.
l, N.
Ｎ−ジメチルアクリルアミド２９７ｇ（３，０モル）を
添加した。297 g (3.0 mol) of N-dimethylacrylamide were added.
還流下で３時間反応した後、水１００＋ａｌを追加し、
更に還流下で１時間反応を行った。反応終了後、反応液
を冷却し、残余のＮ、Ｎ−ジメチルアクリルアミド及び
ジオキサンを除去し、水５００ｍ１を添加後、クロロホ
ルムで抽出を行った。After reacting for 3 hours under reflux, add 100+al of water,
The reaction was further carried out under reflux for 1 hour. After the reaction was completed, the reaction solution was cooled, residual N,N-dimethylacrylamide and dioxane were removed, and 500 ml of water was added, followed by extraction with chloroform.
クロロホルム層を１０重量％塩酸水溶液で洗浄、更に水
で洗浄したのち、硫酸ナトリウムで脱水した。抽出液か
らクロロホルムを留去して７２．４９の結晶を得た。The chloroform layer was washed with a 10% by weight aqueous hydrochloric acid solution, further washed with water, and then dehydrated with sodium sulfate. Chloroform was distilled off from the extract to obtain 72.49 crystals.
上記についてメタノール／アセトンより再結晶を行った
。The above product was recrystallized from methanol/acetone.
得られた結晶について構造解析を行い次のデーターを得
た。Structural analysis was performed on the obtained crystal, and the following data were obtained.
分子構造：
融 点 １５７〜１５８℃ｃｍ−’
３０５０〜２８００，１７０５．１６４Ｇ、１５００．
１４２０’ Ｒ″ＫＢｒ １３９５，１３４０，１
２６５．１１４５’Ｈ−ＮＭＲδεＢｆｆｌ＋、 ３．
０３（Ｓ、６わ、２．９６（Ｓ、６Ｈ）、３．２〜１．
５（ａ、１４Ｈ）Ｍａｓｓ Ｍ” ３１
０［発明の効果］
本発明の化合物は、文献未載の新規物質であり、テトラ
シアノキノジメタン誘導体等の原料として産業上有用な
ものである。Molecular structure: Melting point 157-158℃cm-'
3050-2800, 1705.164G, 1500.
1420'R''KBr 1395,1340,1
265.1145'H-NMRδεBffl+, 3.
03 (S, 6W, 2.96 (S, 6H), 3.2-1.
5 (a, 14H) Mass M” 31
0 [Effect of the Invention] The compound of the present invention is a novel substance that has not been described in any literature, and is industrially useful as a raw material for tetracyanoquinodimethane derivatives and the like.
Claims (1)
キルカルバモイル）エチル〕−１，４−シクロヘキサン
ジオン。 ▲数式、化学式、表等があります▼ 〔ここでＲはアルキル基を示す〕 ２、２，５−ビス〔２−（ジメチルカルバモイル）エチ
ル〕−１，４−シクロヘキサンジオンである特許請求の
範囲第１項記載の化合物。 ３、１，４−シクロヘキサンジオンにピロリジンを反応
させ、続いてＮ，Ｎ−ジアルキルアクリルアミドを反応
せしめることを特徴とする下記一般式で表される２，５
−ビス〔２−（ジアルキルカルバモイル）エチル〕−１
，４−シクロヘキサンジオンの製造法。 ▲数式、化学式、表等があります▼ 〔ここでＲはアルキル基を示す〕[Claims] 1. 2,5-bis[2-(dialkylcarbamoyl)ethyl]-1,4-cyclohexanedione represented by the following general formula. ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [Here, R represents an alkyl group] Claim No. 2, which is 2,2,5-bis[2-(dimethylcarbamoyl)ethyl]-1,4-cyclohexanedione Compound according to item 1. 2,5 expressed by the following general formula, characterized by reacting 3,1,4-cyclohexanedione with pyrrolidine and then reacting with N,N-dialkyl acrylamide.
-bis[2-(dialkylcarbamoyl)ethyl]-1
, 4-cyclohexanedione manufacturing method. ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [Here, R represents an alkyl group]
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP30679587A JPH01146853A (en) | 1987-12-03 | 1987-12-03 | 2,5-substituted-cyclohexane-1,4-dione and production thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP30679587A JPH01146853A (en) | 1987-12-03 | 1987-12-03 | 2,5-substituted-cyclohexane-1,4-dione and production thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH01146853A true JPH01146853A (en) | 1989-06-08 |
Family
ID=17961340
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP30679587A Pending JPH01146853A (en) | 1987-12-03 | 1987-12-03 | 2,5-substituted-cyclohexane-1,4-dione and production thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01146853A (en) |
-
1987
- 1987-12-03 JP JP30679587A patent/JPH01146853A/en active Pending
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