(+/-)-2,2,3-trimethyl-2,3-dihydronaphtho<2,3-b>furan-4,9-quinone | 117560-08-4

• 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: (+/-)-2,2,3-trimethyl-2,3-dihydronaphtho<2,3-b>furan-4,9-quinone
• 英文别名: 2,3-Dihydro-2,2,3-trimethylnaphtho<2,3-b>furan-4,9-dione；2,2,3-trimethyl-2,3-dihydronaphtho[2,3-b]furan-4,9-dione；α-isodunnione；2,2,3-trimethyl-2,3-dihydro-naphtho[2,3-b]furan-4,9-quinone；2,2,3-Trimethyl-2,3-dihydro-naphtho[2,3-b]furan-4,9-chinon；2,2,3-trimethyl-3H-benzo[f][1]benzofuran-4,9-dione
• CAS: 117560-08-4
• 化学式: C₁₅H₁₄O₃
• 分子量: 242.274
• InChiKey: HWKJRSINESSYAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-2,2,3-trimethyl-2,3-dihydronaphtho<2,3-b>furan-4,9-quinone 、 硫酸 生成 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  278.邓尼翁。第二部分

  摘要：

  DOI：

  10.1039/jr9400001493
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 盐酸 作用下， 生成 (+/-)-2,2,3-trimethyl-2,3-dihydronaphtho<2,3-b>furan-4,9-quinone
  参考文献：
  名称：

  321.Dunnione。第一部分

  摘要：

  DOI：

  10.1039/jr9390001522

文献信息

• 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。
• 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。
• Chirogenic [3 + 2]-photocycloaddition reactions of 2-substituted naphthoquinones with cyclic alkenes
  作者：Christiane Müller、Andreas Bauer、Thorsten Bach

  DOI：10.1039/c1pp05049d

  日期：2011.9

  The formal [3 + 2]-photocycloaddition of 2-hydroxy- (2a) and 2-amino-1,4-naphthoquinone (2b) to olefins was studied in various solvents aiming at a possible enantioselective reaction course. The reaction conditions were optimised for irradiation at low temperature in a nonpolar solvent employing external fluorescent lamps as irradiation sources. Best yields for the reaction of 2-hydroxy-1,4-naphthoquinone

  正式的[3 + 2]-光环加成反应的2-羟基-（2a）和2-氨基-1,4-萘醌针对可能的对映选择性反应过程，在各种溶剂中研究了（2b）制烯烃。优化反应条件以在低温下在非极性溶剂中采用外部荧光灯作为辐照源进行辐照。反应的最佳收率2-羟基-1,4-萘醌（2a）与1-甲基-2-丁烯 当使用大量过量的烯烃（200当量）时获得 甲苯在λ＝ 419nm的照射波长下作为溶剂。在这些条件下，各种环状烯烃（环戊烯， 环己烯， 二氢吡喃， 1-甲基环己-1-烯）进行了光环加成，收率为22–84％。的反应2-羟基-1,4-萘醌（2a）可以在-60°C的条件下对映体进行甲苯作为溶剂，采用手性氢键合模板。然而，对映体过量（≤11％）仍然很低。讨论了这种缺乏选择性的可能原因。
• 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.
• Hatzigrigoriou, Evangelia; Spyroudis, Spyros; Varvoglis, Anastasios, Liebigs Annalen der Chemie, 1989, p. 167 - 170
  作者：Hatzigrigoriou, Evangelia、Spyroudis, Spyros、Varvoglis, Anastasios

  DOI：——

  日期：——