tri-O-methylkinafluorenone | 133129-36-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: tri-O-methylkinafluorenone
• 英文别名: 11H-Benzo[b]fluoren-11-one, 4,5,9,10-tetramethoxy-2-methyl-；4,5,9,10-tetramethoxy-2-methylbenzo[b]fluoren-11-one
• CAS: 133129-36-9
• 化学式: C₂₂H₂₀O₅
• 分子量: 364.398
• InChiKey: CVKOPWHRZFOXAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tri-O-methylkinafluorenone 在 吡啶 、 吡啶-2,6-二羧酸 n-氧化物 、 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 ammonium cerium(IV) nitrate 、 sodium acetate 、 calcium carbonate 、 过氧化苯甲酰 作用下， 以 1,4-二氧六环 、 甲醇 、 四氯化碳 、 水 、 乙腈 为溶剂， 反应 69.36h， 生成 Acetic acid 11-[(E)-benzyloxyimino]-4,9-dimethoxy-5,10-dioxo-10,11-dihydro-5H-benzo[b]fluoren-2-ylmethyl ester
  参考文献：
  名称：

  Koyama, Hiroya; Kamikawa, Tadao, Journal of the Chemical Society. Perkin transactions I, 1998, # 2, p. 203 - 209

  摘要：

  DOI：
• 作为产物：
  描述：

  2-碘-3-甲氧基-5-甲基苯甲醛 在 bis-triphenylphosphine-palladium(II) chloride 叔丁基锂 、 sodium acetate 、 pyridinium chlorochromate 作用下， 以 乙醚 、 二氯甲烷 、 N,N-二甲基乙酰胺 为溶剂， 反应 0.02h， 生成 tri-O-methylkinafluorenone
  参考文献：
  名称：

  An intramolecular arylation route to the kinafluorenones

  摘要：

  Intramolecular palladium-mediated arylation approaches to benzo[b]fluorenes have been investigated. The methodology has been applied in a short synthesis of kinafluorenone 2, providing an effective alternative to Friedel-Crafts-based approaches. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00848-0

文献信息

• Kinamycin Biosynthesis. Synthesis, Isolation, and Incorporation of Stealthin C, an Aminobenzo[<i>b</i>]fluorene
  作者：Steven J. Gould、Chris R. Melville、Martha C. Cone、Jiong Chen、John R. Carney

  DOI：10.1021/jo961486y

  日期：1997.1.1

  biosynthesis of the benzo[b]fluorene antibiotic, kinamycin D, has been identified. 11-Amino-4,5,9-trihydroxy-2-methyl-10H-benzo[b]fluoren-10-one was synthesized and shown to be present in extracts of Streptomyces murayamaensisfermentations. A deuterated sample was prepared and shown to be specifically incorporated into kinamycin D. This new intermediate, now named stealthin C, is also the probable hydroxylation

  已经确定了苯并[b]芴类抗生素生物合成中的一种新中间体，金霉素（Kinamycin D）。合成了11-氨基-4,5,9-三羟基-2-甲基-10H-苯并[b]芴-10-酮，并证明其存在于村山链霉菌发酵提取物中。制备了氘代样品，并显示已明确掺入到金那霉素D中。这种新的中间体（现称为隐身蛋白C）也是病毒链球菌产色隐藻毒素A生物合成隐身蛋白A的可能的羟基化底物。
• Annulation Strategies for Benzo[<i>b</i>]fluorene Synthesis:  Efficient Routes to the Kinafluorenone and WS-5995 Antibiotics
  作者：Ghassan Qabaja、Graham B. Jones

  DOI：10.1021/jo0056186

  日期：2000.10.1

  Intramolecular palladium-mediated arylation approaches to benzo[b]fluorenes have been investigated. The methodology has been applied in a short synthesis of tri-O-methylkinafluorenone, providing an effective alternative td Friedel-Crafts-based approaches. During the course of this work, an acid-promoted quinolactonization of naphthoquinones was also developed, providing direct access to either ortho or para isomers as desired. Application of this methodology in syntheses of the antibiotics WS-5995A, WS-5995C, and functional analogues was demonstrated, and antitumoral activity of this class was determined.
• Total synthesis of phenanthroviridin aglycon: the first naturally-occurring benzo[b]phenanthridine
  作者：Makarand P. Gore、Steven J. Gould、Dwight D. Weller

  DOI：10.1021/jo00007a009

  日期：1991.3

  The first synthesis of a naturally occurring benzo[b]phenanthridine has been accomplished via coupling of a cyanophthalide and a substituted bromocinnamate and subsequent transformation of the resulting aryl naphthoquinone carboxylate via formylation, Hoffmann rearrangement, cyclization, and deprotection steps.
• Synthesis of putative intermediates in the biosynthesis of the kinamycin antibiotics: total synthesis of phenanthroviridin aglycon and related compounds
  作者：Makarand P. Gore、Steven J. Gould、Dwight D. Weller

  DOI：10.1021/jo00036a005

  日期：1992.5

  Phenanthroviridin aglycon, 14, recently isolated from Streptomyces viridiochromogenes DSM 3972, and the corresponding pyridone 10 have been synthesized from the common intermediate (bromoaryl)naphthamide 42. This was prepared by condensation of a (trimethylsilyl)ethyl (bromoaryl)cinnamate 36 and a methoxy-substituted cyanophthalide anion 15, providing the ABD rings of the target benzo[b]phenanthridine skeleton. The aglycon 14 was obtained by a sequence of metal-halogen exchange and formylation, Hofmann rearrangement, cyclization, and deprotection. The pyridone was obtained by Hofmann rearrangement, metal-halogen exchange, cyclization, and deprotection. In addition, a route to cinnamate 36 via coumarin 49 was developed which would allow selective protection of the 1-hydroxyl group for synthesis of glycosidic analogues of phenanthroviridin, 13. The methodology developed is useful for preparation of 10, 14, and analogues specifically labeled at C-5 for study of biosynthesis of the kinamycin antibiotics.
• Total syntheses of O-dimethyl stealthins A and C
  作者：Hiroya Koyama、Tadao Kamikawa

  DOI：10.1016/s0040-4039(97)00793-4

  日期：1997.6

  O-4,O-9-Dimethylstealthin A (11-amino-5-hydroxy-2-hydroxymethyl-4,9-dimethoxy-benzo[b]fluoren-10-one) and O-4,O-9-dimethylstealthin C (11-amino-5-hydroxy-4,9-dimethoxy-2-methyl-benzo[b]fluoren-10-one), methylated derivatives of radical scavengers produced by Stereptomyces viridochromogenes, were synthesized using the Suzuki coupling reaction as a key step. (C) 1997 Elsevier Science Ltd.