JPS5940810B2 - Production method of isoprenyl chalcone - Google Patents
Production method of isoprenyl chalconeInfo
- Publication number
- JPS5940810B2 JPS5940810B2 JP14358083A JP14358083A JPS5940810B2 JP S5940810 B2 JPS5940810 B2 JP S5940810B2 JP 14358083 A JP14358083 A JP 14358083A JP 14358083 A JP14358083 A JP 14358083A JP S5940810 B2 JPS5940810 B2 JP S5940810B2
- Authority
- JP
- Japan
- Prior art keywords
- chalcone
- methyl
- butenyloxy
- isoprenyl
- dimethylallyloxy
- 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.)
- Expired
Links
Landscapes
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】
本発明はイソプレニルカルコンの製法に関し、抗消化性
潰瘍活性を呈するイソプレニルカルコンの製法を提供す
るものである。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing isoprenyl chalcone, and provides a method for producing isoprenyl chalcone exhibiting anti-peptic ulcer activity.
本発明は、４’−（ｌ−ｌ−ジメチルアリロキシ）−４
−（３−メチルー ２−ブテニロキシ）カルコンを加熱
転位させて４’ −ハイドロキシー ３’ −（３ーメ
チルー ２−ブテニル）−４−（３−メチル−２−ブテ
ニロキシ）カルコンを得ることを特徴とするイソプレニ
ルカルコンの製法である。The present invention provides 4'-(l-l-dimethylallyloxy)-4
-(3-methyl-2-butenyloxy)chalcone is subjected to thermal rearrangement to obtain 4'-hydroxy 3'-(3-methyl-2-butenyl)-4-(3-methyl-2-butenyloxy)chalcone. This is a method for producing isoprenyl chalcone.
本発明の加熱転位は、４’一（ｌ・ １−ジメチルアリ
ロキシ）−４−（３−メチルー ２−ブテニロキシ）カ
ルコンをジエチルアニリン、ジメチルフオルムアマイド
などの溶剤に溶解もしくは懸濁し、あるいは溶剤を用い
ることなしに窒素の存在下または非存在下に加熱するこ
とによりおこるその１・１−ジメチルアリロキシ基の転
位であり、その結果３−メチルー ２−ブテニル基が３
’位に導入されて４’−ハイドロキシー ３’−（３−
メチルー２−ブテニル）−４−（３−メチルー ２−ブ
テニロキシ）カルコンが生成する。The thermal rearrangement of the present invention is carried out by dissolving or suspending 4'-(l-1-dimethylallyloxy)-4-(3-methyl-2-butenyloxy)chalcone in a solvent such as diethylaniline or dimethylformamide, or rearrangement of the 1,1-dimethylallyloxy group by heating in the presence or absence of nitrogen without the use of
4'-hydroxy 3'-(3-
Methyl-2-butenyl)-4-(3-methyl-2-butenyloxy)chalcone is produced.
４’−（１・１−ジメチルアリロキシ）−４一（３−メ
チルー２−ブテニロキシ）カルコンは、パラ−（１・
１−ジメチルアリロキシ）アセトフェノンとパラ−（３
−メチルー ２−ブテニロキシ）ベンズアルデヒドを有
機溶剤（たとえば、メタノール、エタノール、酢酸エチ
ルなど）に溶解し、これにアルカリ（たとえば、苛性ソ
ーダ、苛性カリなど）または酸（たとえば、塩化水素、
硫酸など）を加え、室温で撹拌または還流して両者を縮
合させることにより得ることができる。4'-(1,1-dimethylallyloxy)-4-(3-methyl-2-butenyloxy) chalcone is para-(1,
1-dimethylallyloxy)acetophenone and para-(3
-Methyl-2-butenyloxy)benzaldehyde is dissolved in an organic solvent (e.g., methanol, ethanol, ethyl acetate, etc.) and added to an alkali (e.g., caustic soda, caustic potash, etc.) or an acid (e.g., hydrogen chloride, etc.).
sulfuric acid, etc.) and stirring or refluxing at room temperature to condense the two.
パラ−（１・１−ジメチルアリロキシ）アセトフェノン
またはパラ−（３−メチルー ２−ブテニロキシ）ベン
ズアルデヒドは、たとえばインディアン・ジャーナル・
オブ・ケミストリー：７、１０７２（１９６９）；同９
、１３２２（１９７１）■ヘミツシエ・ベリヒテ：１０
５、８６３（１９７２）；同１０５、３５１１（１９７
２）：特開昭４９−５９５０号公報または同５０−２４
２５８号公報などに記載の公知の方法によつて製造する
ことができる。Para-(1,1-dimethylallyloxy)acetophenone or para-(3-methyl-2-butenyloxy)benzaldehyde is described, for example, in the Indian Journal
of Chemistry: 7, 1072 (1969);
, 1322 (1971) ■ Hemitssie Berichte: 10
5, 863 (1972); 105, 3511 (197
2): Japanese Patent Application Laid-open No. 49-5950 or 50-24
It can be produced by a known method described in Japanese Patent No. 258 and the like.
本発明で得られた４’ −ハイドロキシー ３’一（３
ーメチルー ２−ブテニル）−４−（３−メチル−２−
ブテニロキシ）カルコンは優れた抗消化性潰瘍活性を示
した。4'-Hydroxy 3'-(3
-Methyl-2-butenyl)-4-(3-methyl-2-
Butenyloxy) chalcone showed excellent anti-peptic ulcer activity.
たとえば、ラツトに３０η／Ｋ９を投与した場合の実験
潰瘍抑制率は、高木の酢酸潰瘍法で５０．２％、幽門結
紮法で９５．７％であつた。For example, when 30η/K9 was administered to rats, the experimental ulcer inhibition rate was 50.2% using Takagi's acetic acid ulcer method and 95.7% using the pylorus ligation method.
以下、実施例を挙げて本発明を具体的に説明する。The present invention will be specifically described below with reference to Examples.
実施例
パラ一（１・１−ジメチルアリロキシ）アセトフエノン
６．０７とパラ一（３−メチル−２−ブテニロキシ）ベ
ンズアルデヒド６．１ｙをエタノール２５ｍ１に溶かし
、５０％苛性カリ水溶液２３０７を加え、室温で３時間
攪拌して縮合物の４′−（１・１−ジメチルアリロキシ
）−４−（３−メチル２−ブテニロキシ）カルコン９．
８７を得た。Example 6.07 of para-(1,1-dimethylallyloxy)acetophenone and 6.1y of para-(3-methyl-2-butenyloxy)benzaldehyde were dissolved in 25 ml of ethanol, 50% aqueous caustic potassium solution 2307 was added, and the 9. Stir for hours to obtain condensate 4'-(1,1-dimethylallyloxy)-4-(3-methyl-2-butenyloxy)chalcone.
I got 87.
この全量をジエチルアニリン７０ηに溶かし、窒素ガス
下１４０℃で４時間攪拌し、４′−ハイドロキシ−３′
−（３−メチル−２−ブテニル）−４（３−メチル−２
−ブテニロキシ）カルコン８．８７を得た。Ｍ．ｐ．ｌ
４５〜１４７℃This whole amount was dissolved in 70η of diethylaniline, stirred at 140°C for 4 hours under nitrogen gas, and 4′-hydroxy-3′
-(3-methyl-2-butenyl)-4(3-methyl-2
-Butenyloxy)chalcone 8.87% was obtained. M. p. l
45-147℃
Claims (1)
−メチル−２−ブテニロキシ）カルコンを加熱転位させ
て４′−ハイドロキシ−３′−（３−メチル−２−ブテ
ニル）−４−（３−メチル−２−ブテニロキシ）カルコ
ンを得ることを特徴とするイソプレニルカルコンの製法
。1 4'-(1,1-dimethylallyloxy)-4-(3
-Methyl-2-butenyloxy) chalcone is subjected to thermal rearrangement to obtain 4'-hydroxy-3'-(3-methyl-2-butenyl)-4-(3-methyl-2-butenyloxy) chalcone. Production method of isoprenyl chalcone.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14358083A JPS5940810B2 (en) | 1983-08-05 | 1983-08-05 | Production method of isoprenyl chalcone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14358083A JPS5940810B2 (en) | 1983-08-05 | 1983-08-05 | Production method of isoprenyl chalcone |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4415274A Division JPS598251B2 (en) | 1974-04-19 | 1974-04-19 | Synthesis method of isoprenyl chalcone |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5946241A JPS5946241A (en) | 1984-03-15 |
| JPS5940810B2 true JPS5940810B2 (en) | 1984-10-03 |
Family
ID=15342038
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14358083A Expired JPS5940810B2 (en) | 1983-08-05 | 1983-08-05 | Production method of isoprenyl chalcone |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5940810B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61112919A (en) * | 1984-11-08 | 1986-05-30 | Sotsukishiya:Kk | Servo clinometer |
-
1983
- 1983-08-05 JP JP14358083A patent/JPS5940810B2/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61112919A (en) * | 1984-11-08 | 1986-05-30 | Sotsukishiya:Kk | Servo clinometer |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5946241A (en) | 1984-03-15 |
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