2-Acetoxy-2,3-dihydronaphtho<2,3-b>furan-4,9-dione | 133700-93-3

• 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-Acetoxy-2,3-dihydronaphtho<2,3-b>furan-4,9-dione
• 英文别名: 2-acetoxy-2,3-dihydro-naphtho[2,3-b]furan-4,9-dione；2-acetoxy-2,3-dihydronaphtho[2,3-b]furan-4,9-dione；(4,9-Dioxo-2,3-dihydrobenzo[f][1]benzofuran-2-yl) acetate
• CAS: 133700-93-3
• 化学式: C₁₄H₁₀O₅
• 分子量: 258.23
• InChiKey: LDEYTNHPXUSVGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  乙酸乙烯酯 、 2-羟基-1,4-萘醌 以 丙酮 为溶剂， 反应 10.0h， 以53%的产率得到2-Acetoxy-2,3-dihydronaphtho<2,3-b>furan-4,9-dione
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1021/jo00010a003

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.
• Synthesis of Furanonaphthoquinones with Hydroxyamino Side Chains
  作者：Chongming Wu、Randall K. Johnson、Michael R. Mattern、Jackson C. Wong、David G. I. Kingston

  DOI：10.1021/np9900019

  日期：1999.7.1

  Several furanonaphthoquinones have shown useful activity in a yeast assay for DNA-damaging agents and cytotoxicity in mammalian cell culture assays. These results, together with the planar aromatic character of the furanonaphthoquinones, suggested that they might be acting as DNA intercalators. In an attempt to improve this activity, various analogues containing a hydroxyamino side chain have been synthesized. The analogues were prepared by standard methods, but some unexpected reactions were observed nonetheless. Thus, 8-formyl-5-methoxy-4,9-dihydronaphtho[2,3-b]furan-4,9-dione (24) showed an unusual reactivity toward reductive amination, with the reaction proceeding further to give one of two different cyclized products, depending on the amination reagent used. Bioassay results indicated that only simple furanonaphthoquines showed activity in a yeast assay for DNA-damaging agents; compounds with a substituted hydroxyamino side chain were uniformly inactive in this assay. Most of the compounds with a substituted hydroxyamino side chain on the furan ring did, however, show cytotoxicity, although none of them was any more active than the simple aldehyde 2-formyl-4,9-dihydronaphtho[2,3-b]furan-4,9-dione (14). This evidence tends to suggest that the furanonaphthoquinones do not serve primarily as DNA intercalators, because if this were the case, they would have been expected to show an increased activity on conversion to their hydroxyamino side chain derivatives.
• 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：——