2-bromo-5-(3,4,5-trioctyloxybenzoyl)thiophene

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-bromo-5-(3,4,5-trioctyloxybenzoyl)thiophene
• 英文别名: (5-Bromothiophen-2-yl)-(3,4,5-trioctoxyphenyl)methanone；(5-bromothiophen-2-yl)-(3,4,5-trioctoxyphenyl)methanone
• 化学式: C₃₅H₅₅BrO₄S
• 分子量: 651.789
• InChiKey: XWKFVDZHDRBSGP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.5
• 重原子数：
  41
• 可旋转键数：
  26
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  73
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-bromo-5-(3,4,5-trioctyloxybenzoyl)thiophene 、 1,6-diethynylpyrene 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 二乙胺 作用下， 以 甲苯 为溶剂， 反应 20.0h， 以38.5%的产率得到1,6-bis{2-[5-(3,4,5-trioctyloxybenzoyl)thien-2-yl]ethynyl}pyrene
  参考文献：
  名称：

  Effect of alkoxy terminal chain length on mesomorphism of 1,6-disubstituted pyrene-based hexacatenar liquid crystals: columnar phase control

  摘要：

  Synthesis and mesophase-transition behaviors of six 1,6-disubstituted pyrene-based hexacatenar liquid crystals 1(n) (n=8-18) are reported here. They were synthesized by the Sonogashira coupling between 1,6-diethynylpyrene and 2-bromothiophene bearing a trialkoxybenzoyl group. The phase-transition behavior was studied by differential scanning calorimetry and polarized optical microscopy; a few mesophase progressions, I-Col/I-X-Col and Col-Sm, were observed, where X was an optically isotropic but un-identified phase. The structures of Col(r), Col(h), and Sm phases were analyzed by the X-ray crystallography, and the effect of the terminal alkoxy chain length on the mesomorphism was evaluated. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.05.111
• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲酸甲酯 在 aluminum (III) chloride 、 氯化亚砜 、 三溴化硼 、 potassium carbonate 、 sodium iodide 、 potassium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 136.0h， 生成 2-bromo-5-(3,4,5-trioctyloxybenzoyl)thiophene
  参考文献：
  名称：

  Effect of alkoxy terminal chain length on mesomorphism of 1,6-disubstituted pyrene-based hexacatenar liquid crystals: columnar phase control

  摘要：

  Synthesis and mesophase-transition behaviors of six 1,6-disubstituted pyrene-based hexacatenar liquid crystals 1(n) (n=8-18) are reported here. They were synthesized by the Sonogashira coupling between 1,6-diethynylpyrene and 2-bromothiophene bearing a trialkoxybenzoyl group. The phase-transition behavior was studied by differential scanning calorimetry and polarized optical microscopy; a few mesophase progressions, I-Col/I-X-Col and Col-Sm, were observed, where X was an optically isotropic but un-identified phase. The structures of Col(r), Col(h), and Sm phases were analyzed by the X-ray crystallography, and the effect of the terminal alkoxy chain length on the mesomorphism was evaluated. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.05.111

文献信息

• Effect of alkoxy terminal chain length on mesomorphism of 1,6-disubstituted pyrene-based hexacatenar liquid crystals: columnar phase control
  作者：Takuji Hirose、Hiroaki Takai、Mizuki Watabe、Hiroyuki Minamikawa、Tatsuya Tachikawa、Koichi Kodama、Mikio Yasutake

  DOI：10.1016/j.tet.2014.05.111

  日期：2014.8

  Synthesis and mesophase-transition behaviors of six 1,6-disubstituted pyrene-based hexacatenar liquid crystals 1(n) (n=8-18) are reported here. They were synthesized by the Sonogashira coupling between 1,6-diethynylpyrene and 2-bromothiophene bearing a trialkoxybenzoyl group. The phase-transition behavior was studied by differential scanning calorimetry and polarized optical microscopy; a few mesophase progressions, I-Col/I-X-Col and Col-Sm, were observed, where X was an optically isotropic but un-identified phase. The structures of Col(r), Col(h), and Sm phases were analyzed by the X-ray crystallography, and the effect of the terminal alkoxy chain length on the mesomorphism was evaluated. (C) 2014 Elsevier Ltd. All rights reserved.