bis(2-[1,3]-dioxolan-2-yl-benzo[b]thiophen-3-yl)-dimethylgermane | 1042734-09-7

• 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: bis(2-[1,3]-dioxolan-2-yl-benzo[b]thiophen-3-yl)-dimethylgermane
• CAS: 1042734-09-7
• 化学式: C₂₄H₂₄GeO₄S₂
• 分子量: 513.174
• InChiKey: VNIHDNFVOOJHHT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.03
• 重原子数：
  31.0
• 可旋转键数：
  4.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  bis(2-[1,3]-dioxolan-2-yl-benzo[b]thiophen-3-yl)-dimethylgermane 在 高氯酸 作用下， 以 水 、 丙酮 为溶剂， 以97%的产率得到bis(2-formylbenzo[b]thiophen-3-yl)dimethylgermane
  参考文献：
  名称：

  Synthesis of Fused 1-Sila-, 1-Germa-, and 1-Selenacyclohepta-2,4,6-trienes

  摘要：

  A concise route to I-sila-, 1-germa-, and I-selenacyclohepta-2,4,6-trienes containing two fused benzo[b]thiophene units is described. Metalation of the ethylene acetal of 3-bromobenzo[b]thiophene2-carboxaldehyde and subsequent quenching with Me2SiCI2, Me2GeCI2, or (PhS02)2Se gave the corresponding bis(benzo[b]thiophen-3-yl)silane, -germane, or -selenide, respectively, which were subjected to deprotection, followed by McMurry coupling, eventually affording the target compounds in good overall yields. It was also concluded that application of this approach to synthesis of related benzo-fused metallacyclohepta-2,4,6-trienes is limited to electron-deficient targets, as attempts involving electronrich substrates faile d or gave only low yields at the final McMurry coupling stage.

  DOI：

  10.1021/om8003114
• 作为产物：
  描述：

  2-(3-bromobenzo[b]thiophen-2-yl)-1,3-dioxolane 、 二氯二甲基锗 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以73%的产率得到bis(2-[1,3]-dioxolan-2-yl-benzo[b]thiophen-3-yl)-dimethylgermane
  参考文献：
  名称：

  Synthesis of Fused 1-Sila-, 1-Germa-, and 1-Selenacyclohepta-2,4,6-trienes

  摘要：

  A concise route to I-sila-, 1-germa-, and I-selenacyclohepta-2,4,6-trienes containing two fused benzo[b]thiophene units is described. Metalation of the ethylene acetal of 3-bromobenzo[b]thiophene2-carboxaldehyde and subsequent quenching with Me2SiCI2, Me2GeCI2, or (PhS02)2Se gave the corresponding bis(benzo[b]thiophen-3-yl)silane, -germane, or -selenide, respectively, which were subjected to deprotection, followed by McMurry coupling, eventually affording the target compounds in good overall yields. It was also concluded that application of this approach to synthesis of related benzo-fused metallacyclohepta-2,4,6-trienes is limited to electron-deficient targets, as attempts involving electronrich substrates faile d or gave only low yields at the final McMurry coupling stage.

  DOI：

  10.1021/om8003114