2-ethoxy-2,3-dihydronaphtho[2,3-b]furan-4,9-dione | 133700-94-4

• 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: 2-ethoxy-2,3-dihydronaphtho[2,3-b]furan-4,9-dione
• 英文别名: 2-Ethoxy-2,3-dihydrobenzo[f][1]benzofuran-4,9-dione
• CAS: 133700-94-4
• 化学式: C₁₄H₁₂O₄
• 分子量: 244.247
• InChiKey: VDCYBKVTEOJCQZ-UHFFFAOYSA-N

物化性质

• 沸点：
  392.5±42.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-ethoxy-2,3-dihydronaphtho[2,3-b]furan-4,9-dione 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 4.0h， 以87%的产率得到萘并(2,3-b)呋喃-4,9-二酮
  参考文献：
  名称：

  FACILE SYNTHESIS OF AVICEQUINONE-B NATURAL PRODUCT

  摘要：

  An efficient synthesis of avicequinone-B (2) and furonaphthoquinone 4 has been carried out starting from 2-hydroxy-1,4-naphthoquinone (6) by CAN-mediated cycloaddition reaction.

  DOI：

  10.1081/scc-120013719
• 作为产物：
  描述：

  2-羟基-1,4-萘醌 、 乙烯基乙醚 在 ammonium cerium(IV) nitrate 、 碳酸氢钠 作用下， 以 乙腈 为溶剂， 以34%的产率得到2-ethoxy-2,3-dihydronaphtho[2,3-b]furan-4,9-dione
  参考文献：
  名称：

  Ceric Ammonium Nitrate Mediated Cycloaddition of Hydroxyquinones with Alkenes for the One-Step Construction of Furoquinone Derivatives

  摘要：

  通过硝酸铈铵介导的 [3+2] 型环加成反应，将 2-羟基-1,4-萘醌和 2-羟基-1,4-苯醌与烯烃或苯基乙炔一步合成呋喃[2,3-b]并萘烷-4,9-二酮、呋喃[1,2-b]并萘烷-4,5-二酮、苯并呋喃-4,7-二酮和苯并呋喃-4,5-二酮衍生物的方法被报道。

  DOI：

  10.1246/cl.1996.451

文献信息

• One-Step Synthesis of Naphthofurandione, Benzofurandione, and Phenalenofuranone Derivatives by the CAN-Mediated Cycloaddition
  作者：Kazuhiro Kobayashi、Tomokazu Uneda、Koujirou Tanaka、Masako Mori、Hideo Tanaka、Osamu Morikawa、Hisatoshi Konishi

  DOI：10.1246/bcsj.71.1691

  日期：1998.7

  The 3+2-type cycloaddition reaction of 2-hydroxy-1,4-naphthoquinones with various alkenes or phenylacetylene was mediated by ammonium cerium(IV) nitrate (CAN) to give the corresponding naphtho[2,3-b]furan-4,9-dione and naphtho[1,2-b]furan-4,5-dione derivatives. The reaction of 2-hydroxy-1,4-benzoquinones with alkenes in the presence of CAN similarly proceeded to give benzofuran-4,7-dione and benzofuran-4,5-dione derivatives. 3-Hydroxy-1H-phenalen-1-one also underwent the CAN-mediated cycloaddition with alkenes or phenylacetylene to give the corresponding 7H-phenaleno[1,2-b]furan-7-one derivatives.

  2-羟基-1,4-萘醌与各种烯烃或苯乙炔在硝酸铈铵（CAN）的催化下发生3+2型环加成反应，生成相应的萘并[2,3-b]呋喃-4,9-二酮和萘并[1,2-b]呋喃-4,5-二酮衍生物。2-羟基-1,4-苯醌与烯烃在CAN存在下同样发生反应，得到苯并呋喃-4,7-二酮和苯并呋喃-4,5-二酮衍生物。3-羟基-1H-菲兰烯-1-酮也能在CAN的催化下与烯烃或苯乙炔发生环加成反应，生成相应的7H-菲兰诺[1,2-b]呋喃-7-酮衍生物。
• 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.
• KOBAYASHI, KAZUHIRO;SHIMIZU, HIDEKI;SASAKI, AKIYOSHI;SUGINOME, HIROSHI, J. ORG. CHEM., 56,(1991) N, C. 3204-3205
  作者：KOBAYASHI, KAZUHIRO、SHIMIZU, HIDEKI、SASAKI, AKIYOSHI、SUGINOME, HIROSHI

  DOI：——

  日期：——
• Ceric Ammonium Nitrate Mediated Cycloaddition of Hydroxyquinones with Alkenes for the One-Step Construction of Furoquinone Derivatives
  作者：Kazuhiro Kobayashi、Masako Mori、Tomokazu Uneda、Osamu Morikawa、Hisatoshi Konishi

  DOI：10.1246/cl.1996.451

  日期：1996.6

  A one-step formation of furoquinones, such as naphtho[2,3-b]furan-4,9-dione, naphtho[1,2-b]furan-4,5-dione, benzofuran-4,7-dione, and benzofuran-4,5-dione derivatives, by the ceric ammonium nitrate mediated [3+2] type cycloaddition of 2-hydroxy-1,4-naphthoquinones and 2-hydroxy-1,4-benzoquinones with alkenes or phenylacetylene is described.

  通过硝酸铈铵介导的 [3+2] 型环加成反应，将 2-羟基-1,4-萘醌和 2-羟基-1,4-苯醌与烯烃或苯基乙炔一步合成呋喃[2,3-b]并萘烷-4,9-二酮、呋喃[1,2-b]并萘烷-4,5-二酮、苯并呋喃-4,7-二酮和苯并呋喃-4,5-二酮衍生物的方法被报道。