4-(6-bromohexyloxymethyl)-2,2'-bi[1,3]dithiolylidene | 627099-77-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二硫醇
• 英文名称: 4-(6-bromohexyloxymethyl)-2,2'-bi[1,3]dithiolylidene
• 英文别名: 4-(6-Bromohexoxymethyl)-2-(1,3-dithiol-2-ylidene)-1,3-dithiole
• CAS: 627099-77-8
• 化学式: C₁₃H₁₇BrOS₄
• 分子量: 397.445
• InChiKey: OPUSGNCGVGARSK-UHFFFAOYSA-N

物化性质

• 沸点：
  413.5±45.0 °C(Predicted)
• 密度：
  1.514±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  110
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(6-bromohexyloxymethyl)-2,2'-bi[1,3]dithiolylidene 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 26.0h， 生成 di[6-([2,2]'-bi[[1,3]dithiolylidene]-4-ylmethoxy)hexyl] disulfide
  参考文献：
  名称：

  Synthesis, Electrochemistry and Self-Assembled Monolayers of Novel Tetrathiafulvalene (TTF) and π-Extended TTF (exTTF) Disulfides

  摘要：

  The synthesis of a new series of tetrathiafalvalene (TTF) and pi-extended TTF (exTTF) disulfides and the electrochemical properties of self-assembled monolayers derived from these compounds are described. When the intermediate bromides 3 and 7 were reacted with thiourea, followed by basic hydrolysis, the expected thiol formation was not observed and only disulfides were obtained. A mechanism is proposed to explain the self-oxidation process of these compounds. For the first time SAMs of exTTF derivatives were prepared. Electrochemical data for SAMS of 6 and 8 reveal a single two-electron chemically reversible oxidation process to form a dicationic state, typical of the exTTF system. The SAMS are stable over extended periods of time and show electrochemical stability upon repeated potential scans.

  DOI：

  10.1021/jo034894s
• 作为产物：
  描述：

  1,6-二溴己烷 、 4-(hydroxymethyl)tetrathiafulvalene 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以43%的产率得到4-(6-bromohexyloxymethyl)-2,2'-bi[1,3]dithiolylidene
  参考文献：
  名称：

  Synthesis, Electrochemistry and Self-Assembled Monolayers of Novel Tetrathiafulvalene (TTF) and π-Extended TTF (exTTF) Disulfides

  摘要：

  The synthesis of a new series of tetrathiafalvalene (TTF) and pi-extended TTF (exTTF) disulfides and the electrochemical properties of self-assembled monolayers derived from these compounds are described. When the intermediate bromides 3 and 7 were reacted with thiourea, followed by basic hydrolysis, the expected thiol formation was not observed and only disulfides were obtained. A mechanism is proposed to explain the self-oxidation process of these compounds. For the first time SAMs of exTTF derivatives were prepared. Electrochemical data for SAMS of 6 and 8 reveal a single two-electron chemically reversible oxidation process to form a dicationic state, typical of the exTTF system. The SAMS are stable over extended periods of time and show electrochemical stability upon repeated potential scans.

  DOI：

  10.1021/jo034894s

文献信息

• Synthesis, Electrochemistry and Self-Assembled Monolayers of Novel Tetrathiafulvalene (TTF) and π-Extended TTF (<i>e</i><i>x</i>TTF) Disulfides
  作者：M. Ángeles Herranz、Lei Yu、Nazario Martín、Luis Echegoyen

  DOI：10.1021/jo034894s

  日期：2003.10.1

  The synthesis of a new series of tetrathiafalvalene (TTF) and pi-extended TTF (exTTF) disulfides and the electrochemical properties of self-assembled monolayers derived from these compounds are described. When the intermediate bromides 3 and 7 were reacted with thiourea, followed by basic hydrolysis, the expected thiol formation was not observed and only disulfides were obtained. A mechanism is proposed to explain the self-oxidation process of these compounds. For the first time SAMs of exTTF derivatives were prepared. Electrochemical data for SAMS of 6 and 8 reveal a single two-electron chemically reversible oxidation process to form a dicationic state, typical of the exTTF system. The SAMS are stable over extended periods of time and show electrochemical stability upon repeated potential scans.