炔酮

在ざい有ゆう机つくえ化学かがく中ちゅう，炔酮（英語えいご：ynone）是ぜ指ゆび结构为 R¹C≡C‒C(=O)R² (其中R² ≠ H) 的てき化合かごう物ぶつ，其中C≡C三さん键位くらい于羰基(C=O)官能かんのう团的αあるふぁ和わβべーた位くらい^[1]，如茵しとね陈二に炔酮是ぜ天然てんねん存在そんざい的てき一いち种炔酮。

合成ごうせい[编辑]

合成ごうせい炔酮的てき一种方法是先将1-炔烃与あずか三甲さんこう基もと铝反はん应，生成せいせい二甲基铝代产物，再さい与あずか酰氯发生酰基取と代だい反はん应得到いた炔酮^[2]。

另一种方法ほう是ぜ1-炔烃与あずか酰氯在ざい纳米铜的催化下か发生反はん应^[3]

其他方法ほうほう包括ほうかつ氧化醛，之これ後ご在ざい有ゆう金きむ催化劑ざい的てき情況じょうきょう下和したお碘代炔反應おう。^[4]

另一いち個こ替かえ代がわ但ただし是ぜ反應はんのう步ふ驟較多た的てき製せい備方式しき涉わたる及利用りよう炔基鋰和一醛發生反應產生二に級きゅう醇あつし後ご，再さい進行しんこう斯文しぶん氧化反はん应。

亚类型がた[编辑]

二に炔酮（Diynone）：分子ぶんし结构中ちゅう存在そんざい两个三键链接一个羰基的てき化合かごう物ぶつ。其中两个三键位于羰基的一侧且共轭的称为共きょう轭二に炔酮（conjugated diynone，如茵しとね陈二に炔酮），两个三键位于羰基的两侧称为跳とべ跃二に炔酮（skipped diynone）；
双そう炔酮（Bis-ynone）：分子ぶんし结构中ちゅう存在そんざい两个炔酮基もと团的化合かごう物ぶつ，分ふん子中こなか的てき两个炔酮基もと团可发生分子ぶんし内ない的てき环加成なり反はん应，形成けいせい呋喃衍生物せいぶつ^[5]。

另见[编辑]

二に酮

参考さんこう文献ぶんけん[编辑]

^ CHEBI:51723 - ynone. ChEBI. ebi.ac.uk. [18 May 2017]. （原始げんし内容ないよう存そん档于2018-02-28）.
^ Wang, Baomin; Bonin, Martine; Micouin, Laurent. A Straightforward Synthesis of Ynones by Reaction of Dimethylalkynylaluminum Reagents with Acid Chlorides. J. Org. Chem. June 22, 2005, 70 (15): 6126–6128. PMID 16018717. doi:10.1021/jo050760y.
^ Weijiang, Sun; Wang, Yan; Wua, Xuan; Yao, Xiaoquan. Palladium-, ligand-, and solvent-free synthesis of ynones by the coupling of acyl chlorides and terminal alkynes in the presence of a reusable copper nanoparticle catalyst. Green Chemistry. 2013, 15 (9): 2356–2360 [18 May 2017]. （原始げんし内容ないよう存そん档于2019-02-16）.
^ Wang, Zhaofeng; Li, Li; Yong, Huang. A General Synthesis of Ynones from Aldehydes via Oxidative C–C bond Cleavage under Aerobic Conditions. J. Am. Chem. Soc. August 18, 2014, 136 (35): 12233–12236. PMID 25133731. doi:10.1021/ja506352b.
^ Wills, M.S.B.; Danheiser, R.L. Intramolecular [4 + 2] Cycloaddition Reactions of Conjugated Ynones. Formation of Polycyclic Furans via the Generation and Rearrangement of Strained Heterocyclic Allenes. J. Am. Chem. Soc. August 28, 1998, 120 (36): 9378–9379. doi:10.1021/ja9819209.

[1] CHEBI:51723 - ynone. ChEBI. ebi.ac.uk. [18 May 2017]. （原始げんし内容ないよう存そん档于2018-02-28）.

[2] Wang, Baomin; Bonin, Martine; Micouin, Laurent. A Straightforward Synthesis of Ynones by Reaction of Dimethylalkynylaluminum Reagents with Acid Chlorides. J. Org. Chem. June 22, 2005, 70 (15): 6126–6128. PMID 16018717. doi:10.1021/jo050760y.

[3] Weijiang, Sun; Wang, Yan; Wua, Xuan; Yao, Xiaoquan. Palladium-, ligand-, and solvent-free synthesis of ynones by the coupling of acyl chlorides and terminal alkynes in the presence of a reusable copper nanoparticle catalyst. Green Chemistry. 2013, 15 (9): 2356–2360 [18 May 2017]. （原始げんし内容ないよう存そん档于2019-02-16）.

[4] Wang, Zhaofeng; Li, Li; Yong, Huang. A General Synthesis of Ynones from Aldehydes via Oxidative C–C bond Cleavage under Aerobic Conditions. J. Am. Chem. Soc. August 18, 2014, 136 (35): 12233–12236. PMID 25133731. doi:10.1021/ja506352b.

[5] Wills, M.S.B.; Danheiser, R.L. Intramolecular [4 + 2] Cycloaddition Reactions of Conjugated Ynones. Formation of Polycyclic Furans via the Generation and Rearrangement of Strained Heterocyclic Allenes. J. Am. Chem. Soc. August 28, 1998, 120 (36): 9378–9379. doi:10.1021/ja9819209.

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