2-(3'-chlorobenzylidene)-4-allyloxy-7-piperidinocarbonyloxy-2,3-dihydro-benzo[b]thiophen-3-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 2-(3'-chlorobenzylidene)-4-allyloxy-7-piperidinocarbonyloxy-2,3-dihydro-benzo[b]thiophen-3-one
• 英文别名: [(2Z)-2-[(3-chlorophenyl)methylidene]-3-oxo-4-prop-2-enoxy-1-benzothiophen-7-yl] piperidine-1-carboxylate
• 化学式: C₂₄H₂₂ClNO₄S
• 分子量: 455.962
• InChiKey: JOBMVHBBTMJFSZ-HKWRFOASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  81.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-acetyl-5-hydroxybenzo[1,3]oxathiol-2-one 在 potassium carbonate 、 二甲基亚砜 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 2-(3'-chlorobenzylidene)-4-allyloxy-7-piperidinocarbonyloxy-2,3-dihydro-benzo[b]thiophen-3-one
  参考文献：
  名称：

  New domino reaction. One pot synthesis of 4,7-dihydroxythioaurone derivatives from benzaldehydes and 4-acetyl-2-oxo-benz[1,3]oxathiole

  摘要：

  A convenient synthesis of 4,7-dihydroxythioaurone derivatives by a one pot reaction of benzaldehydes with 4-acetyl-2-oxobenz[1,3]oxathioles and piperidine acetate in DMSO is described. The structures of the compounds, including double bond geometry were proved unequivocally by NMR methods. The thioaurone ring system seems to be formed by three consecutive reactions: opening of the oxathiolone ring with piperidine, oxidation of the formed mercapto group with DMSO or/and air to disulfide, and condensation with aldehyde. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.06.107

文献信息

• New domino reaction. One pot synthesis of 4,7-dihydroxythioaurone derivatives from benzaldehydes and 4-acetyl-2-oxo-benz[1,3]oxathiole
  作者：Marek T. Konieczny、Wojciech Konieczny、Stefan Wolniewicz、Konstanty Wierzba、Yoshimitsu Suda、Paweł Sowiński

  DOI：10.1016/j.tet.2005.06.107

  日期：2005.9

  A convenient synthesis of 4,7-dihydroxythioaurone derivatives by a one pot reaction of benzaldehydes with 4-acetyl-2-oxobenz[1,3]oxathioles and piperidine acetate in DMSO is described. The structures of the compounds, including double bond geometry were proved unequivocally by NMR methods. The thioaurone ring system seems to be formed by three consecutive reactions: opening of the oxathiolone ring with piperidine, oxidation of the formed mercapto group with DMSO or/and air to disulfide, and condensation with aldehyde. (c) 2005 Elsevier Ltd. All rights reserved.