1,3-二氯-5-(1-辛炔基)苯 | 1034710-62-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1,3-二氯-5-(1-辛炔基)苯
• 英文名称: 1,3-dichloro-5-(1-octynyl)benzene
• 英文别名: 1,3-Dichloro-5-oct-1-ynylbenzene；1,3-dichloro-5-oct-1-ynylbenzene
• CAS: 1034710-62-7
• 化学式: C₁₄H₁₆Cl₂
• 分子量: 255.187
• InChiKey: RRVAGNDHLSHVFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1,3-二氯-5-(1-辛炔基)苯 、 二氧化碳 、 4-(trimethylsilylethynyl)phenylmagnesium bromide 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 21.5h， 以25%的产率得到2'-carboxy-4,4''-bis(trimethylsilylethynyl)-5'-(1-octynyl)-1,1':3',1''-terphenyl
  参考文献：
  名称：

  Double-Stranded Helical Polymers Consisting of Complementary Homopolymers

  摘要：

  Two complementary homopolymers of chiral amidines and achiral carboxylic acids with m-terphenyl-based backbones were synthesized by the copolymerization of a p-diiodobenzene derivative with the diethynyl monomers bearing a chiral amidine group and a carboxyl group using the Sonogashira reaction, respectively. Upon mixing in THF, the homopolymer strands assembled into a preferred-handed double helix through interstrand amidinium-carboxylate salt bridges, as evidenced by its absorption, circular dichroism, and IR spectra. In contrast, when mixed in less polar solvents, such as chloroform, the complementary strands kinetically formed an interpolymer complex with an imperfect double helical structure containing a randomly hybridized cross-linked structure, probably because of strong salt bridge formations. This primary complex was rearranged into the fully double helical structure by treatment with a strong acid followed by neutralization with an amine. High-resolution atomic force microscopy revealed the double-stranded helical structure and enabled the determination of the helical sense.

  DOI：

  10.1021/ja711447s
• 作为产物：
  描述：

  1-辛炔 、 3,5-二氯-1-溴苯 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 反应 24.0h， 以87%的产率得到1,3-二氯-5-(1-辛炔基)苯
  参考文献：
  名称：

  Double-Stranded Helical Polymers Consisting of Complementary Homopolymers

  摘要：

  Two complementary homopolymers of chiral amidines and achiral carboxylic acids with m-terphenyl-based backbones were synthesized by the copolymerization of a p-diiodobenzene derivative with the diethynyl monomers bearing a chiral amidine group and a carboxyl group using the Sonogashira reaction, respectively. Upon mixing in THF, the homopolymer strands assembled into a preferred-handed double helix through interstrand amidinium-carboxylate salt bridges, as evidenced by its absorption, circular dichroism, and IR spectra. In contrast, when mixed in less polar solvents, such as chloroform, the complementary strands kinetically formed an interpolymer complex with an imperfect double helical structure containing a randomly hybridized cross-linked structure, probably because of strong salt bridge formations. This primary complex was rearranged into the fully double helical structure by treatment with a strong acid followed by neutralization with an amine. High-resolution atomic force microscopy revealed the double-stranded helical structure and enabled the determination of the helical sense.

  DOI：

  10.1021/ja711447s

文献信息

• Double-Stranded Helical Polymers Consisting of Complementary Homopolymers
  作者：Takeshi Maeda、Yoshio Furusho、Shin-Ichiro Sakurai、Jiro Kumaki、Kento Okoshi、Eiji Yashima

  DOI：10.1021/ja711447s

  日期：2008.6.1

  Two complementary homopolymers of chiral amidines and achiral carboxylic acids with m-terphenyl-based backbones were synthesized by the copolymerization of a p-diiodobenzene derivative with the diethynyl monomers bearing a chiral amidine group and a carboxyl group using the Sonogashira reaction, respectively. Upon mixing in THF, the homopolymer strands assembled into a preferred-handed double helix through interstrand amidinium-carboxylate salt bridges, as evidenced by its absorption, circular dichroism, and IR spectra. In contrast, when mixed in less polar solvents, such as chloroform, the complementary strands kinetically formed an interpolymer complex with an imperfect double helical structure containing a randomly hybridized cross-linked structure, probably because of strong salt bridge formations. This primary complex was rearranged into the fully double helical structure by treatment with a strong acid followed by neutralization with an amine. High-resolution atomic force microscopy revealed the double-stranded helical structure and enabled the determination of the helical sense.