1,8-ジアザビシクロ[5.4.0]-7-ウンデセン
1,8-ジアザビシクロ[5.4.0]-7-ウンデセン · 2,3,4,6,7,8,9,10-オクタヒドロピリミド[1,2-a]アゼピン · 1,5-ジアザビシクロ[5.4.0]ウンデカ-5-エン · 1,8-ジアザビシクロ[5.4.0]ウンデカン-7-エン · 1,8-ジアザビシクロ[5.4.0]ウンデカ-7-エン · DBU · 1,8-ジアザビシクロ〔5.4.0〕ウンデカ-7-エン · 1,8-ジアザビシクロ-5．4．0-ウンデカ-7-エン
![1,8-ジアザビシクロ[5.4.0]-7-ウンデセン の分子構造式](/img/chemical/81184.png)
識別子と物理属性
| CAS No. | 6674-22-2 |
|---|---|
| 分子式 | C9H16N2 |
| 平均分子量 | 152.24 g/mol |
| 単同位体質量 | 152.13134851 g/mol |
| SMILES | C1CCC2=NCCCN2CC1 |
| InChIKey | GQHTUMJGOHRCHB-UHFFFAOYSA-N |
| PubChem CID | 81184 |
| ChEMBL | CHEMBL1489129 |
| EC No. | 229-713-7 |
| DTXSID | DTXSID2049424 |
| 現地名 | 1,8-ジアザビシクロ[5.4.0]-7-ウンデセン |
化学・物理的性質
| XLogP | 1.4 |
|---|---|
| 極性表面積 | 15.6 |
| 水素結合供与体数 | 0 |
| 水素結合受容体数 | 1 |
| 回転可能結合数 | 0 |
| 重原子数 | 11 |
| 形式電荷 | 0 |
| 複雑度 | 163 |
| 物質分類 | Nitrogen Compounds -> Other Nitrogen Compounds |
| LogP（分配係数） | 1.38 |
| 密度 | 1.018 @25 °C1.019 g/mL at 20 °C(lit.) |
| 蒸気圧 | 0.05 [mmHg]5.3 [mm Hg] @37.700000000000003 °C5.3 mm Hg ( 37.7 °C) |
| Physical Description | LiquidDry PowderLight yellow liquid with unpleasant odor[MSDSonline] |
| Ionization Efficiency | Positive4.242.7Agilent XCTElectrospray ionizationformic acid (5.3nM) |
| 融点 | -70 °C |
| 沸点 | 80-83 °C0.6 mm Hg(lit.) |
| 屈折率 | n20/D 1.523 |
| 引火点 | >230 °F |
| 貯蔵条件 | Store below +30°C. |
| 溶解度 | 溶ける |
| pKa（酸解離定数） | 13.28±0.20(Predicted) |
| 外観・状態 | 液体 |
| 色 | 無色透明～薄黄色 |
| 臭い | 不快 |
| pH | 12.8 (10g/l, H2O, 20℃) |
| 爆発限界 | 1.1-6.5%(V) |
| BRN | 508906 |
| 安定性 | 安定。強酸化剤、酸、酸塩化物、酸無水物とは相容れない。 |
| InChI | 1S/C9H16N2/c1-2-5-9-10-6-4-8-11(9)7-3-1/h1-8H2 |
| InChIKey | GQHTUMJGOHRCHB-UHFFFAOYSA-N |
| SMILES | C1CCN2CCCN=C2CC1 |
| CAS データベース | 6674-22-2(CAS DataBase Reference) |
| NISTの化学物質情報 | 1,8-diazabicyclo [5.4.0]undec-7-ene(6674-22-2) |
| EPAの化学物質情報 | Pyrimido[1,2-a]azepine, 2,3,4,6,7,8,9,10-octahydro- (6674-22-2) |
化学的特性
Colorless to yellow liquid
安全性と法規制
| GHS 分類 | This chemical does not meet GHS hazard criteria for 6.2% (48 of 776) of reports.DangerH290 (18.3%): May be corrosive to metals [Warning Corrosive to Metals]P234, P260, P264, P264+P265, P270, P273, P280, P301+P316, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P330, P362+P364, P363, P390, P405, P406, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 776 reports by companies from 26 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 規制情報 | Chemical: Pyrimido[1,2-a]azepine, 2,3,4,6,7,8,9,10-octahydro-Pyrimido[1,2-a]azepine, 2,3,4,6,7,8,9,10-octahydro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Pyrimido[1,2-a]azepine, 2,3,4,6,7,8,9,10-octahydro- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 19-03-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/102511,8-Diazabicyclo[5.4.0]undec-7-ene: Does not have an individual approval but may be used under an appropriate group standard |
| 有害性の概要 | Harmful after ingestionCorrosive to skinCan cause chemical pneumonitis[MSDSonline] |
| Hazard Classes and Categories | Met. Corr. 1 (18.3%) |
| Protective Action Criteria (PAC) | 1.2 [mg/m3]13 [mg/m3]79 [mg/m3] |
| 有害作用 | Dermatotoxin - Skin burns. |
| F | 34 |
| 水環境危害等級（WGK） | 2 |
| TSCA 収載状態 | TSCA listed |
| 輸送番号（UN） | UN 3267 8/PG 2 |
| 毒性 | LD50 orally in Rabbit: 215 - 681 mg/kg |
| 税関コード | 29339930 |
| 危険文句（R） | 22-34-52/53-35-40-37-19-11-67 |
| 化審法 | (5)-1117 |
| 消防法 | 危-4-3-III |
| 危険表示 | C,F |
| 安全措置（S） | 26-36/37/39-45-61-27-16 |
| 危険等級 | 8Acute Tox. 3 OralAquatic Chronic 3Eye Dam. 1Met. Corr. 1Skin Corr. 1B |
| 包装等級 | II |
| 自然発火温度 | 260 °C |
| 貯蔵分類 | 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials |
用途
解説
1,8-ジアザビシクロ[5.4.0]-7-ウンデセンジアザビシクロウンデセン．略称DBU．ε-カプロラクタムとアクリロニトリルとの反応により生成する．沸点80～83 ℃(80 Pa)．1.018．1.5219．ハロゲン化アルカンに等モル量のDBUを加えると脱ハロゲン化水素が起こりアルケンが生成する．この反応の収率は，類似の1,5-ジアザビシクロ[4.3.0]-5-ノネン(DBN)を用いた場合より高く，ピリジン，キノリンなどの通常の第三級アミンでは満足な結果は得にくい．DBUは活性C-Hをもつ化合物のハロゲン化アルキルによるジアルキル化反応や，クネベナーゲル反応に用いられる．
用途
有機合成(和光試薬時報Vol.63 No.2,p.26(1995))。
説明
DBU is a bicyclic amidine base. It is non-nucleophilic, sterically hindered, tertiary amine base in organic chemistry. It is reported to be superior to amine catalyst in Baylis-Hillman reaction.It promotes the methylation reaction of phenols, indoles and benzimidazoles with dimethyl carbonate under mild conditions.
天然物の起源
Although all commercially available DBU is produced synthetically, it may also be isolated from the sea sponge Niphates digitalis.The biosynthesis of DBU has been proposed to begin with 1,6-hexanedial and 1,3-diaminopropane.
使用
DBU may be used:as catalyst for carboxylic acid esterification with dimethyl carbonatein the synthesis of duocarmycin and CC-1065 analogsas catalyst in aza-Michael addition and Knovenegal condensation reactionas base for dehalogenation of halogenated Diels-Alder adducts and the resulting activated 2,4-dienones were subjected to regio- and stereo-directed Michael additions, using Yamamoto′s reagent (CH3Cu · BF3)in a new synthesis of the ABCD ring system of CamptothecinDBU may be used as an catalyst for the dissolution and activation of cellulose by a reversible reaction of its hydroxyl groups with carbon dioxide. This dissolved cellulose system can be derivatized to form cellulose mixed esters.Used in a new synthesis of the ABCD ring system of Camptothecin.
一般的な説明
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製法・合成法
純化方法
Fractionally distil DBU under vacuum. Also purify it by chromatography on Kieselgel and eluting with CHCl3/EtOH/25% aqueous NH3 (15:5:2) and checking by IR and MS. [Oediger et al. Chem Ber 99 2012 1962, Angew Chem, Int Ed Engl 6 76 1967, Guggisberg et al. Helv Chim Acta 61 1057 1978, Beilstein 23/5 V 271.]