10-phenyl-11-oxa-7-thiabenzo[c]fluoren-8-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 10-phenyl-11-oxa-7-thiabenzo[c]fluoren-8-one
• 英文别名: 15-Phenyl-16-oxa-11-thiatetracyclo[8.7.0.02,7.012,17]heptadeca-1(10),2,4,6,8,12(17),14-heptaen-13-one
• 化学式: C₂₁H₁₂O₂S
• 分子量: 328.391
• InChiKey: BRPAFVGUKHYDBW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N,N-二乙基-1-萘羧酰胺 在 selenium(IV) oxide 、 四甲基乙二胺 、 仲丁基锂 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 异戊醇 为溶剂， 反应 15.0h， 生成 10-phenyl-11-oxa-7-thiabenzo[c]fluoren-8-one
  参考文献：
  名称：

  Application of directed metalation in synthesis. Part 8: Interesting example of chemoselectivity in the synthesis of thioaurones and hydroxy ketones and a novel anionic ortho-Fries rearrangement used as a tool in the synthesis of thienopyranones and thiafluorenones

  摘要：

  Chemoselective synthesis of thioaurones or 3-hydroxy benzo[b]thiophen-2-aryl ketones, 1-hydroxy naphtho[2,1-b]thiophen-2aryl ketones and chalcones from N,N-diethyl-ortho-methyl sulfanyl aryl amides were described. (Benzo[b]thiophen-2-yl) alkylates and (naphtho[2, 1-b]thiophen-2-yl) alkylates undergo a novel anionic ortho-Fries rearrangement leading to (3-hydroxy benzo[b]thiophen-2-yl) and (1-hydroxy naphtho[2, 1 -b]thiophen-2-yl) alkyl ketones. The hydroxy ketones were used as intermediates in the synthesis of wide range of benzothienopyranones and thiafluorenones. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.07.050