1-苯基-1-戊炔-3,4-二酮 | 21772-15-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-苯基-1-戊炔-3,4-二酮
• 英文名称: 1-Phenyl-1-pentyne-3,4-dione
• 英文别名: 5-phenyl-4-pentyne-2,3-dione；1-Phenylpent-1-in-3,4-dion；5-Phenylpent-4-yne-2,3-dione
• CAS: 21772-15-6
• 化学式: C₁₁H₈O₂
• 分子量: 172.183
• InChiKey: WXSGRKRPDGYPSC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-苯基-1-戊炔-3,4-二酮 在 caesium carbonate 、 1,3-双(2,4,6-三甲基苯基)氯化咪唑 作用下， 以 四氢呋喃 为溶剂， 以65%的产率得到6-methyl-2-oxo-4-phenyl-5-(phenylethynyl)-2H-pyran-3-yl acetate
  参考文献：
  名称：

  N-杂环碳烯催化的炔基1,2-二酮

  摘要：

  首次通过N杂环卡宾（NHC）催化实现炔基1,2-二酮的酯化反应，从而可以在非常温和的条件下快速获得多种合成和药学上重要的α-吡喃酮。提出了一种全新的NHC催化的mpolung模式，其中包含O-酰化的烯丙基酯作为关键中间体。此外，据推测，以一系列的基团迁移和新的键形成为特征的空前反应路径证明了产物的形成。

  DOI：

  10.1002/adsc.201700700
• 作为产物：
  描述：

  3-(Benzotriazol-1-yl)-3-ethoxy-1-phenyl-1-pentyn-4-one 在 盐酸 作用下， 以 丙酮 为溶剂， 反应 0.33h， 以92%的产率得到1-苯基-1-戊炔-3,4-二酮
  参考文献：
  名称：

  Novel and Convenient Routes to Functionalized Alkynyl Ketones from 1-(Benzotriazol-1-yl)propargyl Ethyl Ethers

  摘要：

  1-(Benzotriazol-1-yl)propargyl ethyl ethers, readily accessible from propargyl aldehyde diethyl acetals and benzotriazole, undergo smooth Lithiation at the methine carbon and subsequent reactions with alkyl halides, aldehydes, ketones, imines, esters, trialkylsilyl chlorides, dialkyl carbonates, and isocyanates to yield the corresponding substituted ethers. Hydrolysis of these intermediates under acidic conditions affords a wide variety of alkynyl ketones bearing hydroxy, amino, acyl, trimethylsilyl, alkoxycarbonyl, and (alkylamino)carbonyl substituents at the alpha-position in good to excellent overall yields.

  DOI：

  10.1021/jo00128a038

文献信息

• Tetrasubstituted furans from novel [3 + 2] photocycloaddition of conjugated acetylenic α-diketones with alkenes
  作者：Ashis K. Mukherjee、William C. Agosta

  DOI：10.1039/c39940001821

  日期：——

  Photocycloaddition of ketones 1a–c with tetramethylethylene 2 furnishes tetrasubstituted furans 3a–c in isolated yields of ≈85%; a suggested mechanism for formation of 3a involves [3 + 2] cycloaddition by way of an initial biradical 5 to form an intermediate carbene 6, followed by cyclization to the furan.

  酮的光环1A - c ^与四甲基2种配料四取代的呋喃3A - Ç中的≈85％分离产率; 提出的形成3a的机制包括通过初始双自由基5形成[3 + 2]环加成反应，形成中间体卡宾6，然后环化成呋喃。
• Gold-Catalyzed Highly Efficient Access to 3(<i>2H</i>)-Furanones from 2-Oxo-3-butynoates and Related Compounds
  作者：Yuanhong Liu、Meina Liu、Shenghai Guo、Huamin Tu、Yebing Zhou、Hongjun Gao

  DOI：10.1021/ol061059z

  日期：2006.8.1

  gold-catalyzed cyclization reactions of 2-oxo-3-butynoic esters or disubstituted-1,2-diones with a variety of nucleophiles are described, which offer an efficient and straightforward route to substituted 3(2H)-furanones under mild reaction conditions. The Au(III) catalysts are also highly effective in the hydration of these activated alkynes.

  [反应：参见文本]描述了2-氧代-3-丁酸酯或双取代的1,2-二酮与各种亲核试剂的金催化环化反应，它们为取代的3（2H）提供了一种有效而直接的途径-呋喃酮在温和的反应条件下。Au（III）催化剂在这些活化炔烃的水合作用中也非常有效。
• Photoaddition of Alkenes to Conjugated α-Diketones:  Tandem Cyclizations Leading to Tetrasubstituted Furans¹^a
  作者：Ashis K. Mukherjee、Paul Margaretha、William C. Agosta

  DOI：10.1021/jo952079+

  日期：1996.1.1

  Photocycloaddition of 9a-c with 2 leads cleanly to tetrasubstituted furans 12a-c, respectively, in yields of similar to 85%. The reactive triplet is efficiently sensitized by 2-benzoylnaphthalene and quenched by anthracene, indicating that E(T) is in the range 43-58 kcal/mol. A mechanism is proposed involving an alkyl propargyl biradical (as 10) that closes first to a vinyl carbene (as 11) and then to product. Reaction of 9c with 20 furnishes only 22, and this result rules out an alternative mechanism in which the order of steps leading to the carbene is reversed.
• Yashina,O.G. et al., Journal of Organic Chemistry USSR (English Translation), 1968, vol. 4, p. 2032 - 2034
  作者：Yashina,O.G. et al.

  DOI：——

  日期：——
• Mukherjee Ashis K., Agosta William C., J. Chem. Soc. Chem. Commun, (1994) N 16, S 1821-1822
  作者：Mukherjee Ashis K., Agosta William C.

  DOI：——

  日期：——