trans-2,3-Dihydro-2-butyl-3-methylnaphtho<2,3-b>furan-4,9-dione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: trans-2,3-Dihydro-2-butyl-3-methylnaphtho<2,3-b>furan-4,9-dione
• 英文别名: trans-2,3-Dihydro-2-butyl-3-methylnaphtho[2,3-b]furan-4,9-dione；(2R,3S)-2-butyl-3-methyl-2,3-dihydrobenzo[f][1]benzofuran-4,9-dione
• 化学式: C₁₇H₁₈O₃
• 分子量: 270.328
• InChiKey: ARWSWKNEARWCOD-ZWNOBZJWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-羟基-1,4-萘醌 、 2-庚烯 以 丙酮 为溶剂， 反应 20.0h， 生成 trans-2,3-Dihydro-2-methyl-3-butylnaphtho<2,3-b>furan-4,9-dione 、 trans-2,3-Dihydro-2-butyl-3-methylnaphtho<2,3-b>furan-4,9-dione
  参考文献：
  名称：

  Photoinduced molecular transformations. 140. New one-step general synthesis of naphtho[2,3-b]furan-4,9-diones and their 2,3-dihydro derivatives by the regioselective [3 + 2] photoaddition of 2-hydroxy-1,4-naphthoquinones with various alkynes and alkenes: application of the photoaddition to a two-step synthesis of maturinone

  摘要：

  2,3-Dihydronaphtho[2,3-b]furan-4,9-diones can now be produced in one step in 41-83% yields by an unprecedented regioselective [3 + 2] photoaddition of 2-hydroxy-1,4-naphthoquinones with a variety of alkenes. The dihydronaphthofurandiones can be readily transformed into naphtho[2,3-b]furan-4,9-diones. This new photoaddition reaction has been successfully applied to a two-step synthesis of maturinone, a constituent of Cacalia decomposita A Gray. Naphtho[2,3-b]furan-4,9-diones can also be obtained directly by a new [3 + 2] photoaddition of 2-hydroxy-1,4-naphthoquinone with various alkynes in acetone. The photoaddition between 2-hydroxy-1,4-naphthoquinones and alkenes in acetone involves an initial formation of furanohydroquinones, which are oxidized to furanoquinones. A quenching experiment together with the regioselective nature of photoaddition indicate that the photoaddition is a two-step process from a triplet of excited quinones and involves more stabilized polar biradicals or ionic intermediates generated from them by an intramolecular electron transfer from which the furanohydroquinones are formed.

  DOI：

  10.1021/jo00069a023

文献信息

• Photoinduced molecular transformations. 140. New one-step general synthesis of naphtho[2,3-b]furan-4,9-diones and their 2,3-dihydro derivatives by the regioselective [3 + 2] photoaddition of 2-hydroxy-1,4-naphthoquinones with various alkynes and alkenes: application of the photoaddition to a two-step synthesis of maturinone
  作者：Kazuhiro Kobayashi、Hideki Shimizu、Akiyoshi Sasaki、Hiroshi Suginome

  DOI：10.1021/jo00069a023

  日期：1993.8

  2,3-Dihydronaphtho[2,3-b]furan-4,9-diones can now be produced in one step in 41-83% yields by an unprecedented regioselective [3 + 2] photoaddition of 2-hydroxy-1,4-naphthoquinones with a variety of alkenes. The dihydronaphthofurandiones can be readily transformed into naphtho[2,3-b]furan-4,9-diones. This new photoaddition reaction has been successfully applied to a two-step synthesis of maturinone, a constituent of Cacalia decomposita A Gray. Naphtho[2,3-b]furan-4,9-diones can also be obtained directly by a new [3 + 2] photoaddition of 2-hydroxy-1,4-naphthoquinone with various alkynes in acetone. The photoaddition between 2-hydroxy-1,4-naphthoquinones and alkenes in acetone involves an initial formation of furanohydroquinones, which are oxidized to furanoquinones. A quenching experiment together with the regioselective nature of photoaddition indicate that the photoaddition is a two-step process from a triplet of excited quinones and involves more stabilized polar biradicals or ionic intermediates generated from them by an intramolecular electron transfer from which the furanohydroquinones are formed.