2,9-dibromo-4,5,6,7-tetrahydro-5S,6S-dioctyloxybenzothiophene | 462128-31-0

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 2,9-dibromo-4,5,6,7-tetrahydro-5S,6S-dioctyloxybenzothiophene
• 英文别名: (5S,6S)-1,3-dibromo-5,6-dioctoxy-4,5,6,7-tetrahydro-2-benzothiophene
• CAS: 462128-31-0
• 化学式: C₂₄H₄₀Br₂O₂S
• 分子量: 552.454
• InChiKey: ZLBTXDPNEQVSRY-VXKWHMMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.6
• 重原子数：
  29
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  46.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  9,9-二苯基芴-2-硼酸频哪醇酯 、 2,9-dibromo-4,5,6,7-tetrahydro-5S,6S-dioctyloxybenzothiophene 在 四(三苯基膦)钯 tri-tert-butylphosphine 、 potassium carbonate 作用下， 以 乙二醇二甲醚 为溶剂， 以75%的产率得到(5S,6S)-1,3-bis(9,9-diphenylfluoren-2-yl)-5,6-dioctoxy-4,5,6,7-tetrahydro-2-benzothiophene
  参考文献：
  名称：

  Zr-promoted cyclization of diynes bearing C2-chirality: synthesis and properties of new chiral conjugated molecules

  摘要：

  Conjugated oligomers bearing 4,5,6,7-tetrahydro-5S,6S-dioctyloxybenzothiophene as a central linkage were synthesized by Negishi's reagent (n-Bu2ZrCp2) promoted intramolecular cyclization of a diyne and subsequent Suzuki coupling reactions. The chirality in the central linkage originated from tartaric acid, which induced the conjugated backbone of oligomers to exhibit interesting optical activity. (C) Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00520-8
• 作为产物：
  描述：

  (4S,5S)-4,5-dioctoxyocta-1,7-diyne 在 二氯二茂锆 正丁基锂 、 溴 作用下， 以 四氢呋喃 、 四氯化碳 为溶剂， 生成 2,9-dibromo-4,5,6,7-tetrahydro-5S,6S-dioctyloxybenzothiophene
  参考文献：
  名称：

  Zr-promoted cyclization of diynes bearing C2-chirality: synthesis and properties of new chiral conjugated molecules

  摘要：

  Conjugated oligomers bearing 4,5,6,7-tetrahydro-5S,6S-dioctyloxybenzothiophene as a central linkage were synthesized by Negishi's reagent (n-Bu2ZrCp2) promoted intramolecular cyclization of a diyne and subsequent Suzuki coupling reactions. The chirality in the central linkage originated from tartaric acid, which induced the conjugated backbone of oligomers to exhibit interesting optical activity. (C) Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00520-8