2-acetyl-4,5,6,7-tetrahydrobenzofuran-4-one | 50626-09-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 2-acetyl-4,5,6,7-tetrahydrobenzofuran-4-one
• 英文别名: 2-acetyl-6,7-dihydrobenzofuran-4(5H)-one；2-acetyl-6,7-dihydro-5H-1-benzofuran-4-one
• CAS: 50626-09-0
• 化学式: C₁₀H₁₀O₃
• 分子量: 178.188
• InChiKey: DVOGZSGVBNFQAI-UHFFFAOYSA-N

物化性质

• 熔点：
  54-55 °C
• 沸点：
  341.2±42.0 °C(Predicted)
• 密度：
  1.211±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  47.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-acetyl-2,3,4,5,6,7-hexahydrobenzofuran-4-one 在 manganese(IV) oxide 作用下， 以 various solvent(s) 为溶剂， 反应 3.5h， 以67%的产率得到2-acetyl-4,5,6,7-tetrahydrobenzofuran-4-one
  参考文献：
  名称：

  Domino Michael–O-alkylation reaction: one-pot synthesis of 2,4-diacylhydrofuran derivatives and its application to antitumor naphthofuran synthesis

  摘要：

  在THF中，使用DBU作为催化剂，1,3-二羰基化合物的烯醇盐与α-卤代-α,β-不饱和羰基化合物的反应生成2,4-二酰基二氢呋喃衍生物。通过化学二氧化锰氧化这些二氢呋喃，可以得到2,4-二酰基呋喃衍生物。这一方法的应用使得抗肿瘤的萘呋喃天然产物能够通过简短的步骤合成。

  DOI：

  10.1039/b107180g

文献信息

• Regioselective Synthesis of Highly Functionalized Furans Through the Ru^II-Catalyzed [3+2] Cycloaddition of Diazodicarbonyl Compounds
  作者：Likai Xia、Yong Rok Lee

  DOI：10.1002/ejoc.201402067

  日期：2014.6

  A novel method for the RuII-catalyzed regioselective synthesis of highly functionalized furans from readily available cyclic and acyclic diazodicarbonyl compounds and terminal alkynes is described. The devised protocol offers a straightforward means to the construction of a variety of diverse furan derivatives through powerful cascade processes, including the formation of ruthenium carbenoid, cyclopropenation

  描述了一种从容易获得的环状和非环状重氮二羰基化合物和末端炔烃中 RuII 催化区域选择性合成高度官能化呋喃的新方法。设计的协议为通过强大的级联过程构建各种不同的呋喃衍生物提供了一种直接的方法，包括钌卡宾的形成、环丙烯化、开环复分解和环化。
• Chemical, photochemical and enzymatic approach to furylhydroperoxides
  作者：Arrigo Scettri、Francesco Bonadies、Alessandra Lattanzi、Laura Palombi、Silvia Pesci

  DOI：10.1016/s0040-4020(97)10135-1

  日期：1997.12

  Furylhydroperoxides are accessible by three different methodologies. In the enzymatic approach, lypoxygenase is employed on non lipid-like substrates. Transition metal catalyzed epoxidation of allylic alcohols is strongly dependent on the structure of the involved hydroperoxide.

  呋喃基氢过氧化物可通过三种不同的方法获得。在酶促方法中，在非脂质样底物上使用了加氧合酶。过渡金属催化的烯丙基醇的环氧化强烈依赖于所涉及的氢过氧化物的结构。
• Tandem Nucleophilic Reaction Leading to Hydrofurans: Application to One-Pot Synthesis of Antitumor Naphthofuran Natural Product
  作者：Hisahiro Hagiwara、Kouji Sato、Toshio Suzuki、Masayoshi Ando

  DOI：10.3987/com-98-8430

  日期：——

  The reaction of enolates of 1,3-dicarbonyl compounds (1) with 3,4-dibromo-2-butanone (2) afforded hydrofuran derivatives (4) or (5) in the presence of DBU in THF and the reaction was applied to the one-pot synthesis of antitumor naphthofuran natural products (29).
• Rhodium(II)‐Catalyzed Reaction of Iodonium Ylides with Electron‐Deficient and Conjugated Alkynes: Efficient Synthesis of Substituted Furans
  作者：Yong Rok Lee、Sang Heum Yoon

  DOI：10.1080/00397910600631957

  日期：2006.6

  The rhodium(II)-catalyzed reactions of iodonium ylides with electron-deficient and conjugated alkynes have been examined. These reactions provide a rapid route to the preparation of furan derivatives with a variety of substituents on the furan ring.
• Dipolar cycloaddition of cyclic rhodium carbenoids to digonal carbon. Synthesis of isoeuparin
  作者：Michael C. Pirrung、Jiancun Zhang、Andrew T. Morehead

  DOI：10.1016/s0040-4039(00)73398-3

  日期：1994.8

  Diazocyclohexanediones undergo dipolar cycloadditions with substituted acetylenes to provide 2-substituted tetrahydrobenzofuran-4-ones and with allenes to provide 2(H)-3-methylenedihydrofuranones.