キヌクリジン

キヌクリジン[1]
優先IUPAC名
1-Azabicyclo[2.2.2]octane[2]
別称
Quinuclidine[2]
識別情報
CAS登録番号 100-76-5 チェック
PubChem 7527
ChemSpider 7246 チェック
UNII XFX99FC5VI ×
EC番号 202-887-1
ChEBI
ChEMBL CHEMBL1209648 チェック
バイルシュタイン 103111
Gmelin参照 26726
特性
化学式 C7H13N
モル質量 111.18 g mol−1
密度 0.97 g/cm3
融点

157 - 160 °C, 270 K, -99 °F

沸点

149.5 °C, 423 K, 301 °F (760 mmHg)

酸解離定数 pKa 11.0（共役酸）
危険性
GHSピクトグラム 腐食性物質急性毒性(高毒性)急性毒性（低毒性）
GHSシグナルワード 危険(DANGER)
Hフレーズ H301, H310, H315, H318
Pフレーズ P262, P264, P264+265, P270, P280, P301+316, P302+352, P305+354+338, P316, P317, P321, P330, P332+317, P361+364
引火点 36.5 °C (97.7 °F; 309.6 K)
特記なき場合、データは常温 (25 °C)・常圧 (100 kPa) におけるものである。

キヌクリジン (quinuclidine) は複素環式アミンの一種である。分子式 C7H13N、分子量 111.18、CAS登録番号は100-76-5、IUPAC名は1-アザビシクロ[2.2.2]オクタン 1-azabicyclo[2.2.2]octane である。ピペリジンの架橋体とも言える構造を有している。1,4-エタノピペリジン、1,4-エチレンピペリジンと呼ばれることもある。

天然物としてはキニーネの骨格に含まれている。「キヌクリジン」という名も、「quinine」＋「nuclear」（核）から命名されたものである。合成医薬としては、頻尿治療剤ソリフェナシンなどがこの構造を含む。

性質・用途

DABCOなどと同様に、環構造によってアルキル基が後ろ手に縛られた構造をとっているために窒素上の非共有電子対まわりの立体障害が小さく、鎖状のアミンと比較すると求核性が著しく高いことが特徴である。これを生かし、森田・ベイリス・ヒルマン反応の触媒などとして用いられることが多い。

キヌクリジンの2位がカルボニル基に置換されたキヌクリドン (quinuclidone) は、アミドでありながら加水分解しやすく、酸と塩を作るなど、通常のアミドとは違った性質を示す[3]。

参考文献

  1. ^ Quinuclidine Archived October 15, 2007, at the Wayback Machine. at Sigma-Aldrich
  2. ^ a b Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. (2014). p. 169. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4. "The name quinuclidine is retained for general nomenclature only (see Table 2.6)." 
  3. ^ Tani, K.; Stoltz, BM. (2006). "Synthesis and structural analysis of 2-quinuclidonium tetrafluoroborate." Nature 441 (7094): 731–734. doi:10.1038/nature04842. PMID 16760973.

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