3,5-二甲基萘并[2,3-b]呋喃-4,9-二酮 | 22985-02-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: 3,5-二甲基萘并[2,3-b]呋喃-4,9-二酮
• 英文名称: maturinone
• 英文别名: Naphtho(2,3-b)furan-4,9-dione, 3,5-dimethyl-；3,5-dimethylbenzo[f][1]benzofuran-4,9-dione
• CAS: 22985-02-0
• 化学式: C₁₄H₁₀O₃
• 分子量: 226.232
• InChiKey: CPZYZLPKCIMJGW-UHFFFAOYSA-N

物化性质

• 熔点：
  163-166 °C
• 沸点：
  403.5±45.0 °C(Predicted)
• 密度：
  1.297±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  47.3
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2932999099

反应信息

• 作为产物：
  描述：

  [(2R,3R)-3,5-dimethyl-4,9-dioxo-2,3-dihydrobenzo[f][1]benzofuran-2-yl] acetate 生成 3,5-二甲基萘并[2,3-b]呋喃-4,9-二酮
  参考文献：
  名称：

  KOBAYASHI, KAZUHIRO;SHIMIZU, HIDEKI;SASAKI, AKIYOSHI;SUGINOME, HIROSHI, J. ORG. CHEM., 56,(1991) N, C. 3204-3205

  摘要：

  DOI：

文献信息

• Total Synthesis of Maturinone through a Regioselective Diels-Alder Reaction of 5-Brominated Benzofurandione.
  作者：Omar CHERKAOUI、Pascal NEBOIS、Houda FILLION

  DOI：10.1248/cpb.45.457

  日期：——

  Maturinone was efficiently prepared by means of a regiocontrolled Diels-Alder reaction between 5-bromo-2-ethoxycarbonyl-3-methylbenzo[b]furan-4, 7-dione 8 and penta-1, 3-diene.

  通过5-溴-2-乙氧基羰基-3-甲基苯并[b]呋喃-4,7-二酮8和五-1,3-二烯之间的区域控制Diels-Alder反应，有效地制备了马图里酮。
• 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.
• Photoinduced molecular transformations. Part 120. New one-step general synthesis of 2,3-dihydronaphtho[2,3-b]-furan-4,9-diones by regioselective photoaddition of 2-hydroxy-1,4-naphthoquinones with various alkenes and its application to a two-step synthesis of maturinone
  作者：Kazuhiro Kobayashi、Hideki Shimizu、Akiyoshi Sasaki、Hiroshi Suginome

  DOI：10.1021/jo00010a003

  日期：1991.5

  A one-step formation of 2,3-dihydronaphtho-[2,3-b]furan-4,9-diones in 41-83% by a new 2 + 3 type regioselective photoaddition of 2-hydroxy-1,4-naphthoquinones with a variety of alkenes is reported. The dihydronaphthofurandiones can readily be transformed into naphtho[2,3-b]furan-4,9-diones including a natural quinone, maurinone.