2-benzyloxy(diisopropyl)silyl-5-bromothiophene | 1379771-69-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 2-benzyloxy(diisopropyl)silyl-5-bromothiophene
• 英文别名: (5-Bromothiophen-2-yl)-phenylmethoxy-di(propan-2-yl)silane；(5-bromothiophen-2-yl)-phenylmethoxy-di(propan-2-yl)silane
• CAS: 1379771-69-3
• 化学式: C₁₇H₂₃BrOSSi
• 分子量: 383.425
• InChiKey: HCXLTTWIVGHPDY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  37.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [2,2'-bithiophen]-5-yldiisopropylsilanol 、 2-benzyloxy(diisopropyl)silyl-5-bromothiophene 在 bis(η3-allyl-μ-chloropalladium(II)) 、 三苯胂 、 caesium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 24.0h， 生成 Phenylmethoxy-di(propan-2-yl)-[5-(5-thiophen-2-ylthiophen-2-yl)thiophen-2-yl]silane
  参考文献：
  名称：

  An iterative approach to the synthesis of thiophene-based organic dyes

  摘要：

  We developed an iterative synthetic method for oligo-aryl compounds using an organosilicon-based palladium-catalyzed cross-coupling reaction. Aryl compounds containing a benzyloxy(diisopropyl)silyl group (masked Si group) had sufficient chemical stability, and the unmasking step proceeded in a high yield under mild conditions. Both of the key unmasking/coupling steps required no strict anhydrous or degassed conditions. The developed procedure was used for the synthesis of thiophene-based organic dyes for dye-sensitized solar cells. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.04.059
• 作为产物：
  描述：

  2-benzyloxy(diisopropyl)silyl-thiophene 在 N-溴代丁二酰亚胺(NBS) 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以85%的产率得到2-benzyloxy(diisopropyl)silyl-5-bromothiophene
  参考文献：
  名称：

  An iterative approach to the synthesis of thiophene-based organic dyes

  摘要：

  We developed an iterative synthetic method for oligo-aryl compounds using an organosilicon-based palladium-catalyzed cross-coupling reaction. Aryl compounds containing a benzyloxy(diisopropyl)silyl group (masked Si group) had sufficient chemical stability, and the unmasking step proceeded in a high yield under mild conditions. Both of the key unmasking/coupling steps required no strict anhydrous or degassed conditions. The developed procedure was used for the synthesis of thiophene-based organic dyes for dye-sensitized solar cells. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.04.059

文献信息

• An iterative approach to the synthesis of thiophene-based organic dyes
  作者：Shinichiro Fuse、Hayato Yoshida、Takashi Takahashi

  DOI：10.1016/j.tetlet.2012.04.059

  日期：2012.6

  We developed an iterative synthetic method for oligo-aryl compounds using an organosilicon-based palladium-catalyzed cross-coupling reaction. Aryl compounds containing a benzyloxy(diisopropyl)silyl group (masked Si group) had sufficient chemical stability, and the unmasking step proceeded in a high yield under mild conditions. Both of the key unmasking/coupling steps required no strict anhydrous or degassed conditions. The developed procedure was used for the synthesis of thiophene-based organic dyes for dye-sensitized solar cells. (C) 2012 Elsevier Ltd. All rights reserved.