9-fluorodibenzo[b,d]thiophen-1-ol | 1459190-76-1

• 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: 9-fluorodibenzo[b,d]thiophen-1-ol
• 英文别名: 9-Fluorodibenzothiophen-1-ol；9-fluorodibenzothiophen-1-ol
• CAS: 1459190-76-1
• 化学式: C₁₂H₇FOS
• 分子量: 218.251
• InChiKey: ZZZLQAYSLRKRMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  48.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  O-(2',6-difluoro-6'-hydroxy-[1,1'-biphenyl]-2-yl) dimethylcarbamothioate 以 N-甲基吡咯烷酮 为溶剂， 反应 4.0h， 以29%的产率得到9-fluorodibenzo[b,d]thiophen-1-ol
  参考文献：
  名称：

  Dibenzo[bc,fg][1,4]oxathiapentalene: an elusive molecule?

  摘要：

  Dibenzo[bc,fg][1,4]dithiapentalene (1) has previously been prepared by an intramolecular nucleophilic aromatic substitution (SNAr) reaction of 9-fluorodibenzo[b,d]thiophen-1-thiol (X, Y = S). Instead, subjecting 9-fluorodibenzo[b,d]benzofuran-1-ol (X, Y = O) to similar reaction conditions provided a macrocycle (5), as a result of an intermolecular SNAr cyclization, rather than dibenzo[bc,fg][1,4]dioxapentalene (3). To shed further light on this reaction type, we here present an attempt to prepare the mixed (O,S) compound dibenzo[bc,fg][1,4]oxathiapentalene (7) from 9-fluorodibenzo[b,d]thiophen-1-ol (11, X = S, Y = O). However, like a previous strategy to make this molecule, the attempt failed. We rationalize the results by a computational study of the reaction energetics and profiles of the SNAr reactions.[GRAPHICS].

  DOI：

  10.1080/17415993.2013.789515

文献信息

• Dibenzo[<i>bc,fg</i>][1,4]oxathiapentalene: an elusive molecule?
  作者：Virginia Mazzanti、Eduardo Antonio Della Pia、Martyn Jevric、Tue Heesgaard Jepsen、Anders Kadziola、Ole Hammerich、Mogens Brøndsted Nielsen

  DOI：10.1080/17415993.2013.789515

  日期：2013.12.1

  Dibenzo[bc,fg][1,4]dithiapentalene (1) has previously been prepared by an intramolecular nucleophilic aromatic substitution (SNAr) reaction of 9-fluorodibenzo[b,d]thiophen-1-thiol (X, Y = S). Instead, subjecting 9-fluorodibenzo[b,d]benzofuran-1-ol (X, Y = O) to similar reaction conditions provided a macrocycle (5), as a result of an intermolecular SNAr cyclization, rather than dibenzo[bc,fg][1,4]dioxapentalene (3). To shed further light on this reaction type, we here present an attempt to prepare the mixed (O,S) compound dibenzo[bc,fg][1,4]oxathiapentalene (7) from 9-fluorodibenzo[b,d]thiophen-1-ol (11, X = S, Y = O). However, like a previous strategy to make this molecule, the attempt failed. We rationalize the results by a computational study of the reaction energetics and profiles of the SNAr reactions.[GRAPHICS].