2,2,3,3-tetramethyl-2,3-dihydronaphtho[1,2-b]furan-4,5-dione | 178931-47-0

• 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: 2,2,3,3-tetramethyl-2,3-dihydronaphtho[1,2-b]furan-4,5-dione
• 英文别名: 2,2,3,3-Tetramethylbenzo[g][1]benzofuran-4,5-dione
• CAS: 178931-47-0
• 化学式: C₁₆H₁₆O₃
• 分子量: 256.301
• InChiKey: UYKFRXJJCKUXQO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  对硝基甲苯 、 2,2,3,3-tetramethyl-2,3-dihydronaphtho[1,2-b]furan-4,5-dione 生成 2,3-Dihydro-2,2,3,3-tetramethylnaphtho<2,3-b>furan-4,9-dione
  参考文献：
  名称：

  Cooke; Somers, Australian Journal of Scientific Research, Series A: Physical Sciences, 1950, vol. 3, p. 466,477

  摘要：

  DOI：
• 作为产物：
  描述：

  2-hydroxy-3-(1,1,2-trimethyl-allyl)-[1,4]naphthoquinone 在 硫酸 作用下， 生成 2,2,3,3-tetramethyl-2,3-dihydronaphtho[1,2-b]furan-4,5-dione
  参考文献：
  名称：

  Cooke; Somers, Australian Journal of Scientific Research, Series A: Physical Sciences, 1950, vol. 3, p. 466,477

  摘要：

  DOI：

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。
• Synthesis, Anti-Proliferative Activity Evaluation and 3D-QSAR Study of Naphthoquinone Derivatives as Potential Anti-Colorectal Cancer Agents
  作者：Julio Acuña、Jhoan Piermattey、Daneiva Caro、Sven Bannwitz、Luis Barrios、Jairo López、Yanet Ocampo、Ricardo Vivas-Reyes、Fabio Aristizábal、Ricardo Gaitán、Klaus Müller、Luis Franco

  DOI：10.3390/molecules23010186

  日期：——

  active (1.73 < IC50 < 18.11 μM). The naphtho[2,3-b]thiophene-4,9-dione analogs showed potent cytotoxicity, 8-hydroxy-2-(thiophen-2-ylcarbonyl)naphtho[2,3-b]thiophene-4,9-dione being the compound with the highest potency and selectivity. Our results suggest that the toxicity is improved in molecules with tricyclic naphtho[2,3-b]furan-4,9-dione and naphtho[2,3-b]thiophene-4,9-dione systems 2-substituted

  大肠癌（CRC）是一种高发病率和高死亡率的疾病，是全世界癌症死亡的第四大最常见原因。萘醌由于其生物学和结构特性而成为有吸引力的化合物。在这项工作中，合成了36种萘醌衍生物，并评估了它们对HT-29细胞的活性。总体而言，在该系列的大多数成员中均观察到了高到中度的抗增殖活性，其中15种化合物被归类为有活性的（1.73
• 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。
• COMPOUND FOR TREATMENT OR PREVENTION OF PROSTATE-RELATED DISEASES AND PHARMACEUTICAL COMPOSITION OF COLON DELIVERY SYSTEM CONTAINING THE SAME
  申请人：Kwak Taehwan

  公开号：US20100239685A1

  公开（公告）日：2010-09-23

  Provided is a naphthoquinone-based compound represented by Formula 1 or 2 having therapeutic effect on the treatment and/or prevention of prostate and/or testicle (seminal glands)-related diseases, and to a pharmaceutical composition of intestinal delivery system containing the same.
• [EN] COMPOUND FOR TREATMENT OR PREVENTION OF PROSTATE-RELATED DISEASES AND PHARMACEUTICAL COMPOSITION OF COLON DELIVERY SYSTEM CONTAINING THE SAME<br/>[FR] COMPOSÉ POUR LE TRAITEMENT OU LA PRÉVENTION DE MALADIES EN RELATION AVEC LA PROSTATE ET COMPOSITIONS PHARMACEUTIQUES DE SYSTÈME D'ADMINISTRATION PAR LE COLON CONTENANT CE COMPOSÉ
  申请人：MD BIOALPHA CO LTD

  公开号：WO2008066298A1

  公开（公告）日：2008-06-05

  [EN] Provided is a naphthoquinone-based compound represented by Formula 1 or 2 having therapeutic effect on the treatment and/or prevention of prostate and/or testicle (seminal glands)-related diseases, and to a pharmaceutical composition of intestinal delivery system containing the same.
  [FR] La présente invention concerne un composé à base de naphtoquinone représenté par la formule (I) ou (II) présentant un effet thérapeutique pour le traitement et/ou la prévention de maladies se rapportant à la prostate et/ou aux testicules. L'invention concerne également une composition pharmaceutique de système d'administration par le colon contenant ce composé.