JPH0112757B2 - - Google Patents
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- Publication number
- JPH0112757B2 JPH0112757B2 JP60046850A JP4685085A JPH0112757B2 JP H0112757 B2 JPH0112757 B2 JP H0112757B2 JP 60046850 A JP60046850 A JP 60046850A JP 4685085 A JP4685085 A JP 4685085A JP H0112757 B2 JPH0112757 B2 JP H0112757B2
- Authority
- JP
- Japan
- Prior art keywords
- siy
- formula
- group
- groups
- derivatives
- 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
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- -1 Substituted-1,3-butadiene Chemical class 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- SDRZFSPCVYEJTP-UHFFFAOYSA-N 1-ethenylcyclohexene Chemical class C=CC1=CCCCC1 SDRZFSPCVYEJTP-UHFFFAOYSA-N 0.000 claims description 4
- 238000007363 ring formation reaction Methods 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 229910052723 transition metal Inorganic materials 0.000 claims description 2
- 150000003624 transition metals Chemical class 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical class C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000006087 Silane Coupling Agent Substances 0.000 description 2
- HWCCZVRBWGLIGI-UHFFFAOYSA-N buta-1,3-dien-2-yl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C(=C)C=C HWCCZVRBWGLIGI-UHFFFAOYSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- SHWZFQPXYGHRKT-FDGPNNRMSA-N (z)-4-hydroxypent-3-en-2-one;nickel Chemical compound [Ni].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O SHWZFQPXYGHRKT-FDGPNNRMSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 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
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- WPMIPVPRTQDJHJ-UHFFFAOYSA-N buta-1,3-dien-2-yl(tributoxy)silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)C(=C)C=C WPMIPVPRTQDJHJ-UHFFFAOYSA-N 0.000 description 1
- DEMRFFKCHVQCFJ-UHFFFAOYSA-N buta-1,3-dien-2-yl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)C(=C)C=C DEMRFFKCHVQCFJ-UHFFFAOYSA-N 0.000 description 1
- HVNLGTJPHUIWEO-UHFFFAOYSA-N buta-1,3-dien-2-yl(triethyl)silane Chemical compound CC[Si](CC)(CC)C(=C)C=C HVNLGTJPHUIWEO-UHFFFAOYSA-N 0.000 description 1
- FVGLDROEOWZWEY-UHFFFAOYSA-N buta-1,3-dien-2-yl-tri(propan-2-yloxy)silane Chemical compound CC(C)O[Si](OC(C)C)(OC(C)C)C(=C)C=C FVGLDROEOWZWEY-UHFFFAOYSA-N 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 150000001935 cyclohexenes Chemical class 0.000 description 1
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical class C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Description
【発明の詳細な説明】
(イ) 産業上の利用分野
本発明は、構造式〔〕で表される新規なビニ
（式中、Y1、Y2、Y3は低級アルコキシ基、Ｘは
水素原子又はSiY1Y2Y3基を示す。[Detailed description of the invention] (a) Industrial application field (In the formula, Y 1 , Y 2 , Y 3 are lower alkoxy groups, and X is a hydrogen atom or a SiY 1 Y 2 Y 3 group.
但し、Ｘの一つは常にSiY1Y2Y3基であるが、
同時にSiY1Y2Y3基ではない。）ルシクロヘキセ
ン誘導体及びその製造法に関するものである。 However, one of X is always SiY 1 Y 2 Y 3 group,
At the same time, it is not 3 SiY 1 Y 2 Y groups. ) cyclohexene derivatives and their production methods.
(ロ) 従来の技術
従来より、２−トリエチルシリル−１，３−ブ
タジエンは知られて〔テトラヘドロンレターズ
（Tetra−hedoron Letters）、36巻、3323頁〕お
り、ハロゲン原子、アルキル基及びアルコキシ基
と２位の珪素原子が結合した新規な２−置換−
１，３−ブタジエン誘導体については、本発明者
が特願昭59−33733号及び特願昭59−277154号で
提案している。(b) Prior art 2-triethylsilyl-1,3-butadiene has been known [Tetra-hedoron Letters, Vol. 36, p. 3323], and it has been known to contain halogen atoms, alkyl groups, and alkoxy groups. A novel 2-substitution in which the and the silicon atom at the 2nd position are bonded.
Regarding 1,3-butadiene derivatives, the present inventor proposed them in Japanese Patent Application No. 59-33733 and Japanese Patent Application No. 59-277154.
しかし、これらが環元したビニルシクロヘキセ
ン誘導体は知られていない。 However, vinylcyclohexene derivatives in which these are converted into rings are not known.
(ハ) 発明の概要
本発明者らは、構造式〔〕で表される
（式中、Y1、Y2、Y3は低級アルコキシ基を示
す。）
置換−１，３−ブタジエニルシラン誘導体の反応
性について鋭意検討した結果、新規化合物である
前記構造式〔〕で表される化合物が得られると
共に、この化合物がシランカツプリング剤をはじ
め、種々の用途に有効に使用される事を知見し、
本発明を完成するに至つたものである。(c) Summary of the invention The present inventors have discovered that (In the formula, Y 1 , Y 2 , and Y 3 represent lower alkoxy groups.) As a result of intensive studies on the reactivity of substituted-1,3-butadienylsilane derivatives, the above structural formula [], which is a new compound, was found. It was discovered that the compound represented by the formula was obtained, and that this compound could be effectively used for various purposes including as a silane coupling agent.
This has led to the completion of the present invention.
特に、本発明化合物は二個の反応性シリル基を
有する為従来のシランカツプリング剤に比しその
性能が向上する事及び末端ビニール基を有する為
各種の有用な化合物の製造が可能となる事が期待
される。 In particular, since the compound of the present invention has two reactive silyl groups, its performance is improved compared to conventional silane coupling agents, and because it has a terminal vinyl group, it is possible to produce various useful compounds. There is expected.
以下、本発明につき更に詳しく説明する。 The present invention will be explained in more detail below.
(ニ) 発明の構成
本発明に係る新規ビニルシクロヘキセン誘導体
は前記構造式〔〕で表されるもので、具体的に
は１−トリメトキシシリル−４−（1′−トリメト
キシシリルビニル）−シクロヘキセン−１、１−
トリエトキシシリル−４−（1′−トリエトキシシ
リルビニル）−シクロヘキセン−１、１−トリイ
ソプロポキシ−４−（1′−トリイソプロポキシシ
リルビニル）−シクロヘキセン−１、１−トリブ
トキシ−４−（1′−トリブトキシシシリルビニル）
−シクロヘキセン−１、１，４−ジ−（トリメト
キシシリル）−４−ビニル−シクロヘキセン−１、
１，４−ジ−（トリエトキシシリル）−４−ビニル
−シクロヘキセン−１、１，４−ジ−（トリイソ
プロポキシシシリル）−４−ビニル−シクロヘキ
セン−１、１，４−ジ−（トリブトキシリル）−４
−ビニル−シクロヘキセン−１等を挙げる事が出
来る。(d) Structure of the invention The novel vinylcyclohexene derivative according to the present invention is represented by the above structural formula [], and specifically, 1-trimethoxysilyl-4-(1'-trimethoxysilylvinyl)-cyclohexene -1, 1-
Triethoxysilyl-4-(1'-triethoxysilylvinyl)-cyclohexene-1,1-triisopropoxy-4-(1'-triisopropoxysilylvinyl)-cyclohexene-1,1-tributoxy-4-( 1′-tributoxysilylvinyl)
-cyclohexene-1, 1,4-di-(trimethoxysilyl)-4-vinyl-cyclohexene-1,
1,4-di-(triethoxysilyl)-4-vinyl-cyclohexene-1,1,4-di-(triisopropoxysilyl)-4-vinyl-cyclohexene-1,1,4-di-(tri butoxylyl)-4
-vinyl-cyclohexene-1 and the like.
本発明に使用される構造式〔〕で表される置
換−１，３−ブタジエニルシラン誘導体として
は、２−〔トリメトキシ〕シリル−１，３−ブタ
ジエン、２−〔トリエトキシ〕シリル−１，３−
ブタジエン、２−〔トリイソプロポキシ〕シリル
−１，３−ブタジエン、２−〔トリブトキシ〕シ
リル−１，３−ブタジエン、等も挙げられる。 The substituted-1,3-butadienylsilane derivatives represented by the structural formula [] used in the present invention include 2-[trimethoxy]silyl-1,3-butadiene, 2-[triethoxy]silyl-1, 3-
Also included are butadiene, 2-[triisopropoxy]silyl-1,3-butadiene, 2-[tributoxy]silyl-1,3-butadiene, and the like.
本発明に於ける置換−１，３−ブタジエニルシ
ラン誘導体の環化反応は、無溶媒でも行う事が出
来るが、溶媒の使用が望ましい。 Although the cyclization reaction of substituted-1,3-butadienylsilane derivatives in the present invention can be carried out without a solvent, it is preferable to use a solvent.
反応に使用される溶媒としてはジエチルエーテ
ル、ベンゼン、トルエン、キシレン、ヘキサン及
びシクロヘキサン等が挙げられる。 Examples of the solvent used in the reaction include diethyl ether, benzene, toluene, xylene, hexane, and cyclohexane.
尚、反応液の希釈割合は反応熱、容積効率等を
考慮して適宜決める事が出来る。 Incidentally, the dilution ratio of the reaction solution can be appropriately determined in consideration of reaction heat, volumetric efficiency, etc.
反応温度は−50℃〜溶媒の沸点が好ましく、特
に室温で充分反応は進行する。 The reaction temperature is preferably -50 DEG C. to the boiling point of the solvent, and the reaction proceeds particularly well at room temperature.
反応時間は10分間〜５時間、特に30分間〜２時
間とする事が好ましい。 The reaction time is preferably 10 minutes to 5 hours, particularly 30 minutes to 2 hours.
環化反応は無触媒でも進行するが、触媒を使用
する事も出来る。特に、２−〔トリクロロ〕シリ
ル−１，３−ブタジエンの場合は無溶媒、無触媒
で充分反応は進行する。 The cyclization reaction proceeds without a catalyst, but a catalyst can also be used. In particular, in the case of 2-[trichloro]silyl-1,3-butadiene, the reaction proceeds satisfactorily without a solvent or catalyst.
触媒としては、鉄、コバルト、ニツケル、パラ
ジウム、ロジウム及びジルコニウム等の遷移金属
体とハロンゲン化アルキルアルミニウム及び、ア
ルキルアルミニウム等の有機アルミニウム化合物
の組合せ等が挙げられる。 Examples of the catalyst include a combination of a transition metal such as iron, cobalt, nickel, palladium, rhodium, and zirconium, an alkyl aluminum halide, and an organic aluminum compound such as an alkyl aluminum compound.
次に、実施例を挙げて本発明を説明するが、本
発明はこれら実施例に制限されるものではない。 Next, the present invention will be explained with reference to Examples, but the present invention is not limited to these Examples.
実施例 １
反応容器に２−〔トリメトキシ〕シリル−１，
３−ブタジエン（30.21ミリモル）とジエチルエ
ーテル55ml及びニツケルアセチルアセトナート
（0.06ミリモル）を仕込む。この溶液に撹拌しな
がら室温で塩素化ジエチルアルミニウム（0.06ミ
リモル）をゆつくり加える。室温で５時間反応
後、３規定塩酸で触媒を分解しジエチルエーテル
で抽出する。このジエチルエーテル溶液を飽和食
塩水で洗浄し硫酸マグネシウムで乾燥後、ジエチ
ルエーテルを減圧下留去しガスクロ分析を行つ
た。Example 1 2-[trimethoxy]silyl-1,
Charge 3-butadiene (30.21 mmol), 55 ml of diethyl ether and nickel acetylacetonate (0.06 mmol). Add diethylaluminum chloride (0.06 mmol) slowly to this solution at room temperature while stirring. After reacting for 5 hours at room temperature, the catalyst was decomposed with 3N hydrochloric acid and extracted with diethyl ether. This diethyl ether solution was washed with saturated brine and dried over magnesium sulfate, then the diethyl ether was distilled off under reduced pressure and subjected to gas chromatography analysis.
２−〔トリメトキシ〕シリル−１，３−ブタジ
エン環化生成物の収率85％であつた。尚、環化生
成物は下式〔イ〕及び〔ロ〕の50：50の混合物で
あつた。 The yield of the 2-[trimethoxy]silyl-1,3-butadiene cyclization product was 85%. The cyclized product was a 50:50 mixture of the following formulas [a] and [b].
1H−NMR（CDCl3）、内標テトラメチルシラ
ン
異性体〔イ〕
δ6.3（ｍ、1H、CH＝）、5.6〜6.0（ｍ、1H、CH
＝）、4.8〜5.15（ｍ、2H、＝CH2）、3.59（ｓ、9H、
OCH3）、3.57＆3.56（ｓ、9H、OCH3）、1.7〜2.4
（ｍ、6H、CH2、CH＝）
異性体〔ロ〕
δ6.3（ｍ、1H、CH＝）、5.68（ｓ、2H、＝CH2）、
3.59（ｓ、9H、OCH3）、3.53（ｓ、9H、OCH3）、
3.57＆3.56（ｓ、9H、OCH3）、1.7〜2.4（ｍ、7H、
CH2、CH＝）。 1 H-NMR (CDCl 3 ), internally designated tetramethylsilane isomer [a] δ6.3 (m, 1H, CH=), 5.6-6.0 (m, 1H, CH
= ), 4.8-5.15 (m, 2H, = CH 2 ), 3.59 (s, 9H,
OCH3 ), 3.57 & 3.56 (s, 9H, OCH3 ), 1.7~2.4
(m, 6H, CH 2 , CH=) Isomer [b] δ6.3 (m, 1H, CH=), 5.68 (s, 2H, =CH 2 ),
3.59 (s, 9H, OCH 3 ), 3.53 (s, 9H, OCH 3 ),
3.57 & 3.56 (s, 9H, OCH 3 ), 1.7~2.4 (m, 7H,
CH2 , CH=).
Claims (1)
水素原子又はSiY1Y2Y3基を示す。但し、Ｘの一
つは常にSiY1Y2Y3基であるが、同時に
SiY1Y2Y3基ではない。）ビニルシクロヘキセン
誘導体。 ２ 構造式〔〕で表される置換−１，３−ブタ
ジ （式中、Y1、Y2、Y3は低級アルコキシ基を示
す。） エニルシラン誘導体を環化する事を特徴とする構
造式〔〕で表される （式中、Y1、Y2、Y3は低級アルコキシ基、Ｘは
水素原子又はSiY1Y2Y3基を示す。 但し、Ｘの一つは常にSiY1Y2Y3基であるが、
同時にSiY1Y2Y3基ではない。）ビニルシクロヘ
キセン誘導体の製造法。 ３ 遷移金属錯体及び有機アルミニウム化合物の
存在下、環化反応を行う事を特徴とする特許請求
の範囲第２項の製造法。[Claims] 1 Represented by the structural formula [] (In the formula, Y 1 , Y 2 , Y 3 are lower alkoxy groups, and X is a hydrogen atom or a SiY 1 Y 2 Y 3 group. However, one of the Xs is always a SiY 1 Y 2 Y 3 group. ,at the same time
Not 3 SiY 1 Y 2 Y groups. ) Vinylcyclohexene derivatives. 2 Substituted-1,3-butadiene represented by the structural formula [] (In the formula, Y 1 , Y 2 , and Y 3 represent lower alkoxy groups.) Represented by the structural formula [ ] characterized by cyclizing an enylsilane derivative. (In the formula, Y 1 , Y 2 , Y 3 are lower alkoxy groups, and X is a hydrogen atom or a SiY 1 Y 2 Y 3 group. However, one of the X is always a SiY 1 Y 2 Y 3 group. ,
At the same time, it is not 3 SiY 1 Y 2 Y groups. ) Method for producing vinylcyclohexene derivatives. 3. The production method according to claim 2, characterized in that the cyclization reaction is carried out in the presence of a transition metal complex and an organoaluminum compound.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60046850A JPS61205284A (en) | 1985-03-09 | 1985-03-09 | Vinylcyclohexene derivative and production thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60046850A JPS61205284A (en) | 1985-03-09 | 1985-03-09 | Vinylcyclohexene derivative and production thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61205284A JPS61205284A (en) | 1986-09-11 |
| JPH0112757B2 true JPH0112757B2 (en) | 1989-03-02 |
Family
ID=12758812
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60046850A Granted JPS61205284A (en) | 1985-03-09 | 1985-03-09 | Vinylcyclohexene derivative and production thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61205284A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2632162B2 (en) * | 1987-07-29 | 1997-07-23 | 株式会社ブリヂストン | Silane coupling agent |
-
1985
- 1985-03-09 JP JP60046850A patent/JPS61205284A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61205284A (en) | 1986-09-11 |
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