4-Methoxyspiro[7H-furo[3,2-g][1]benzopyran-7,1'-cyclohexan]-5(6H)-one | 187242-01-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 4-Methoxyspiro[7H-furo[3,2-g][1]benzopyran-7,1'-cyclohexan]-5(6H)-one
• 英文别名: 4-methoxyspiro[6H-furo[3,2-g]chromene-7,1'-cyclohexane]-5-one
• CAS: 187242-01-9
• 化学式: C₁₇H₁₈O₄
• 分子量: 286.328
• InChiKey: IAYAMFSSUCAZET-UHFFFAOYSA-N

物化性质

• 沸点：
  466.3±45.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  48.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-Methoxyspiro[7H-furo[3,2-g][1]benzopyran-7,1'-cyclohexan]-5(6H)-one 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以88%的产率得到4-methoxy-7-pentamethylenefuro[3,2-g]chroman-5-ol
  参考文献：
  名称：

  某些新的取代的呋喃呋喃二氢醌衍生物的合成与反应

  摘要：

  用visnaginone 1a和khellinone 1b缩合不同的环状酮，可得到spirofurochromanone衍生物2a-f。化合物2a和2b易于脱甲基，得到化合物3a和3b。硝化2b和2e分别得到硝基呋喃酮和醌衍生物4和5。苯并二氢吡喃-4-醇衍生物6A和图6B是从还原得到图2b和2e中，其直接脱水制得化合物7a中和7b分别。另外，制备了酰胺6c，其在酸水解时不能提供6d。色烯7a的溴化得到相应的9-溴衍生物7c，而未能得到化合物8。用NBS处理2b得到相应的2,9-二溴衍生物10。的二氢吡喃2B和2E分别用羟胺，苯肼，苯胺和多聚甲醛反应，得到的产品11A-E和12A，12B。

  DOI：

  10.1016/s0040-4020(97)10032-1
• 作为产物：
  描述：

  1-(6-羟基-4-甲氧基-1-苯并呋喃-5-基)乙酮 、 环己酮 在 哌啶 作用下， 以 甲苯 为溶剂， 以95%的产率得到4-Methoxyspiro[7H-furo[3,2-g][1]benzopyran-7,1'-cyclohexan]-5(6H)-one
  参考文献：
  名称：

  某些新的取代的呋喃呋喃二氢醌衍生物的合成与反应

  摘要：

  用visnaginone 1a和khellinone 1b缩合不同的环状酮，可得到spirofurochromanone衍生物2a-f。化合物2a和2b易于脱甲基，得到化合物3a和3b。硝化2b和2e分别得到硝基呋喃酮和醌衍生物4和5。苯并二氢吡喃-4-醇衍生物6A和图6B是从还原得到图2b和2e中，其直接脱水制得化合物7a中和7b分别。另外，制备了酰胺6c，其在酸水解时不能提供6d。色烯7a的溴化得到相应的9-溴衍生物7c，而未能得到化合物8。用NBS处理2b得到相应的2,9-二溴衍生物10。的二氢吡喃2B和2E分别用羟胺，苯肼，苯胺和多聚甲醛反应，得到的产品11A-E和12A，12B。

  DOI：

  10.1016/s0040-4020(97)10032-1

文献信息

• Synthesis of Some Chromanone Derivatives and the Use of DNA in Evaluation of their Biological Activity
  作者：El-Sayed I. El-Desoky、Emad. M. El-Telbani、Mahmoud A. Hammad

  DOI：10.1515/znb-1998-0823

  日期：1998.8.1

  6-Formyl-7-hydroxy-5-methoxy-2-pentamethylenechromanone (2) was prepared from the naturally occurring “Visnagin” and condensed with benzil, o-phenylenediamine and 3,4-diaminobenzophenone to give the corresponding imidazolylchromanone derivatives 3-5. Knoevenagel reaction of compound 2 with different active methylene compounds afforded benzodipyranone derivatives 12a - c which may be considered as analogues to the naturally occurring “Xanthyletin and Graveolone Compounds”. The structural formula of the new compounds were established by using different methods for their preparation in addition to the instrumental analyses. Some compounds in this study were biologically evaluated for their ability to bind to DNA.

  摘要：从天然存在的“维斯纳金”制备了6-甲醛基-7-羟基-5-甲氧基-2-戊二亚甲基色酮(2)，并与苯二酮、邻苯二胺和3,4-二氨基苯基酮缩合，得到相应的咪唑基色酮衍生物3-5。化合物2与不同活性亚甲基化合物的Knoevenagel反应得到苯二吡喃酮衍生物12a-c，可视为天然存在的“黄酮类和格雷沃隆类化合物”的类似物。通过不同方法的制备和仪器分析，确定了新化合物的结构式。本研究中的一些化合物已经进行了生物学评估，以评估它们与DNA结合的能力。
• Synthesis and reactions of some new substituted spirofurochromanone derivatives
  作者：El-Sayed I. El-Desoky、Mahmoud A. Hammad、Nabil Grant、Emad M. El-Telbany、Abdel Rahman H. Abdel-Rahman

  DOI：10.1016/s0040-4020(97)10032-1

  日期：1997.11

  chroman-4-ol derivatives 6a and 6b were obtained from reduction of 2b and 2e which were directly dehydrated to give compounds 7a and 7b respectively. Also, amide 6c was prepared which failed to provide 6d on acid hydrolysis. Bromination of the chromene 7a gave the corresponding 9-bromo derivative 7c and failed to give compound 8. Treatment of 2b with NBS afforded the corresponding 2,9-dibromo derivative 10.

  用visnaginone 1a和khellinone 1b缩合不同的环状酮，可得到spirofurochromanone衍生物2a-f。化合物2a和2b易于脱甲基，得到化合物3a和3b。硝化2b和2e分别得到硝基呋喃酮和醌衍生物4和5。苯并二氢吡喃-4-醇衍生物6A和图6B是从还原得到图2b和2e中，其直接脱水制得化合物7a中和7b分别。另外，制备了酰胺6c，其在酸水解时不能提供6d。色烯7a的溴化得到相应的9-溴衍生物7c，而未能得到化合物8。用NBS处理2b得到相应的2,9-二溴衍生物10。的二氢吡喃2B和2E分别用羟胺，苯肼，苯胺和多聚甲醛反应，得到的产品11A-E和12A，12B。
• Preparation of new polycyclic compounds derived from benzofurans and furochromones. An approach to novel 1,2,3-thia-, and selena-diazolofurochromones of anticipated antitumor activities
  作者：Sanaa M.Sh. Atta、Dalia S. Farrag、Ayman M.K. Sweed、A.H. Abdel-Rahman

  DOI：10.1016/j.ejmech.2010.07.065

  日期：2010.11

  Base catalyzed condensation of enaminoketones (3a,b) with malononitrile yields the respective 7-imino-5[2(substituted)prop-1-enyl]furochromene-6-carbonitriles (4a-d) according to the nature of base used. Compounds (3a, b) condense also with indan-1,3-diketone (5) to give alpha, beta-unsaturated carbonyl compounds (6a) and (6b), respectively. Pyrrolidine-catalyzed condensation of visnaginone (2a) and khellinone (2b) with active methylenes yields the corresponding 1-[7,7-(substituted) furobenzodihydropyrone derivatives (7a-e) which condense with semicarbazide to give the respective semicarbazones (8a-e). Compounds (8b,e) react with thionyl chloride to give the respective 1,2,3-thiadiazoles (9a,b) meanwhile compounds (8a-e) react also with selenium dioxide to give 1,2,3-selenadiazoles (9c-g), respectively. Chalcones (11a,b) were obtained upon condensing (2a,b) with ferrocene-2-carboxaldehyde (10). Compatible elementary and spectroscopic measurements were in good accord with the structures postulated for the new compounds. The antitumor activities of certain selected new compounds were screened, in vitro, against a panel of four (breast: MCF-7, cervix: HELA, colon: HCT116 and liver: HEPG2) human solid tumor cell lines and the structure activity relationship (SAR) was discussed. (C) 2010 Elsevier Masson SAS. All rights reserved.