benzo[b]thiophen-3-yl propionate | 849193-34-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: benzo[b]thiophen-3-yl propionate
• 英文别名: propionic acid benzo[b]thiophen-3-yl ester；Propionsaeure-benzo[b]thiophen-3-ylester；1-Benzothiophen-3-yl propanoate
• CAS: 849193-34-6
• 化学式: C₁₁H₁₀O₂S
• 分子量: 206.265
• InChiKey: NXGKDBACFVFWGY-UHFFFAOYSA-N

物化性质

• 沸点：
  324.3±15.0 °C(Predicted)
• 密度：
  1.233±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  benzo[b]thiophen-3-yl propionate 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 以73%的产率得到1-(3-hydroxybenzo[b]thiophen-2-yl)propan-1-one
  参考文献：
  名称：

  定向金属化在合成中的应用。第7部分：适当官能化的苯并[ b ]噻吩的合成作为苯并噻吩并吡喃酮合成中的关键中间体

  摘要：

  一锅合成由邻甲基硫烷基芳基N，N-二乙基酰胺与1-（3-羟基苯并[ b ]噻吩-2-基）乙酮和1合成（3-羟基苯并[ b ]噻吩-2-基）芳基甲酮描述了经由阴离子邻-Fries重排的-（3-羟基苯并[ b ]噻吩-2-基）丙-1-酮。羟基酮用作苯并噻吩并吡喃酮合成中的关键中间体。

  DOI：

  10.1016/j.tetlet.2005.01.038
• 作为产物：
  描述：

  N,N-二乙基苯甲酰胺 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 benzo[b]thiophen-3-yl propionate
  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

• McClelland et al., Journal of the Chemical Society, 1948, p. 81,84
  作者：McClelland et al.

  DOI：——

  日期：——
• 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
  作者：Tarun Kanti Pradhan、Asish De、Jacques Mortier

  DOI：10.1016/j.tet.2005.07.050

  日期：2005.9

  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.
• Application of directed metalation in synthesis. Part 7: Synthesis of suitably functionalised benzo[b]thiophenes as key intermediates in the synthesis of benzothienopyranones
  作者：Tarun Kanti Pradhan、Asish De

  DOI：10.1016/j.tetlet.2005.01.038

  日期：2005.2

  1-(3-hydroxybenzo[b]thiophen-2-yl)ethanone and 1-(3-hydroxybenzo[b]thiophen-2-yl)propan-1-one via an anionic ortho-Fries rearrangement are described. The hydroxy ketones were used as key intermediates in the synthesis of benzothienopyranones.

  一锅合成由邻甲基硫烷基芳基N，N-二乙基酰胺与1-（3-羟基苯并[ b ]噻吩-2-基）乙酮和1合成（3-羟基苯并[ b ]噻吩-2-基）芳基甲酮描述了经由阴离子邻-Fries重排的-（3-羟基苯并[ b ]噻吩-2-基）丙-1-酮。羟基酮用作苯并噻吩并吡喃酮合成中的关键中间体。