2-butylnaphtho[2,3-b]furan-4,9-dione | 62452-68-0

• 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-butylnaphtho[2,3-b]furan-4,9-dione
• 英文别名: 2-butyl-naphtho[2,3-b]furan-4,9-dione；Naphtho[2,3-b]furan-4,9-dione, 2-butyl-；2-butylbenzo[f][1]benzofuran-4,9-dione
• CAS: 62452-68-0
• 化学式: C₁₆H₁₄O₃
• 分子量: 254.285
• InChiKey: QMJCSBGORWODMQ-UHFFFAOYSA-N

物化性质

• 熔点：
  160 °C
• 沸点：
  417.2±34.0 °C(Predicted)
• 密度：
  1.224±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  47.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-hydroxy-3(1'-hexenyl)-1,4-naphthoquinone 在 mercury(II) diacetate 、 溶剂黄146 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 以39.2%的产率得到2-butylnaphtho[2,3-b]furan-4,9-dione
  参考文献：
  名称：

  萘醌衍生物作为潜在的抗结直肠癌药物的合成，抗增殖活性评估和3D-QSAR研究。

  摘要：

  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

  DOI：

  10.3390/molecules23010186

文献信息

• A Complete and Unambiguous 1H and 13C NMR Signals Assignment of para- Naphthoquinones, ortho- and para-Furanonaphthoquinones
  作者：Tatiane Borgati、José de Souza、Alaíde de Oliveira

  DOI：10.21577/0103-5053.20190009

  日期：——

  A complete and unambiguous assignment of H and C nuclear magnetic resonance (NMR) signals of 29 naphthoquinones is reported on the basis of oneand two-dimensional NMR techniques (H, C, H-H correlated spectroscopy (COSY) and H-C heteronuclear multiple-bond correlation (HMBC)). This is the first report distinguishing data between para-naphthoquinones, orthoand para-furanonaphthoquinones isomers.

  基于一维和二维NMR技术（H，C，HH相关光谱（COSY）和HC异核多键相关（ HMBC））。这是第一份区分对萘醌，邻和对呋喃萘甲醌异构体的数据的报告。
• NOVEL PREPARATION OF ANTICANCER-ACTIVE TRICYCLIC COMPOUNDS VIA ALKYNE COUPLING REACTION
  申请人：IIDA Akira

  公开号：US20120077986A1

  公开（公告）日：2012-03-29

  The present invention is directed to provide a novel preparation of anticancer-active tricyclic compounds via alkyne coupling reaction. The present invention provides a process for preparing a compound of formula (Ia) or (Ib): wherein R 1 is optionally substituted C 1-6 alkyl, etc.; W is O, S or NR 2 ; R 2 is hydrogen atom, etc., which comprises Step (a) in which a compound of formula (II): wherein R 1 is the same as defined above, and a compound of formula (III) or (IV): wherein R 2 is the same as defined above; R 3 is hydrogen atom, etc.; X is halogen atom, etc., are reacted in the presence of a base, a copper catalyst and a palladium catalyst in an aprotic polar solvent.

  本发明旨在通过炔烃偶联反应提供一种新型抗癌活性三环化合物的制备方法。本发明提供了一种制备式(Ia)或(Ib)的化合物的方法：其中R1为可选择的取代的C1-6烷基等；W为O、S或NR2；R2为氢原子等；其中包括步骤(a)，其中式(II)的化合物：其中R1与上述定义相同，和式(III)或(IV)的化合物：其中R2与上述定义相同；R3为氢原子等；X为卤原子等，在无水极性溶剂中，在碱、铜催化剂和钯催化剂的存在下反应。
• One-pot synthesis of naphtho[2,3-b]furan-4,9-diones by sequential coupling/ring closure reactions
  作者：Kazuhiro Kobayashi、Tomokazu Uneda、Masataka Kawakita、Osamu Morikawa、Hisatoshi Konishi

  DOI：10.1016/s0040-4039(96)02462-8

  日期：1997.2

  or cuprous oxide in N-methylpiperidine or pyridine, respectively, furnished the corresponding 2-substituted naphtho[2,3-b]furan-4,9-diones in moderate to good yields. The utility of this method was demonstrated in the synthesis of a cytotoxic natural product, 2-(1-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione.

  在双（三苯基膦）氯化钯-碘化亚铜催化剂或氧化亚铜在N-甲基哌啶或吡啶中存在的情况下，用末端乙炔处理3-苯基碘碘-1,2,4-三氧-1,2,3,4-四氢萘分别以中等至良好的产率提供了相应的2-取代的萘并[2,3 - b ]呋喃-4,9-二酮。在合成细胞毒性天然产物2-（1-羟乙基）萘并[2,3 - b ]呋喃-4,9-二酮中证明了该方法的实用性。
• 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.
• THE DDQ MEDIATED CYCLIZATION PRODUCTS OF SOME 2-HYDROXY-3-(1?-ALKENYL)-1,4-NAPHTHOQUINONES
  作者：Farouk Ameer、Robin Giles、Ivan Green、Kyatanahalli Nagabhushana

  DOI：10.1081/scc-120002120

  日期：——

  The DDQ mediated cyclisation products derived from 2-hydroxy-3-(1'-alkenyl)-1,4-napthoquinones viz. (17) under bar were found to be temperature dependent. At 60degreesC the naphthofuranquinone (19) under bar was the predominant isomer whereas at 8degreesC, the naphthopyranquinone (18) under bar was exclusively formed.