(naphtho[2,1-b]thiophen-1-yl) acetate | 866784-19-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (naphtho[2,1-b]thiophen-1-yl) acetate
• 英文别名: 1-acetoxy-naphtho[2,1-b]thiophene；1-Acetoxy-naphtho[2,1-b]thiophen；benzo[e][1]benzothiol-1-yl acetate
• CAS: 866784-19-2
• 化学式: C₁₄H₁₀O₂S
• 分子量: 242.298
• InChiKey: OULKGKOUYDFXOY-UHFFFAOYSA-N

物化性质

• 沸点：
  413.9±18.0 °C(Predicted)
• 密度：
  1.311±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.98
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (naphtho[2,1-b]thiophen-1-yl) acetate 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 以55%的产率得到1-(1-hydroxynaphtho[2,1-b]thiophen-2-yl)ethan-1-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
• 作为产物：
  描述：

  N,N-二乙基-1-萘羧酰胺 在 四甲基乙二胺 、 仲丁基锂 、 sodium hydride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 生成 (naphtho[2,1-b]thiophen-1-yl) acetate
  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

文献信息

• DE439290
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  公开号：——

  公开（公告）日：——