2-((trimethylsilyl)ethynyl)-4,5-dihexyl-1-iodobenzene | 155259-17-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-((trimethylsilyl)ethynyl)-4,5-dihexyl-1-iodobenzene
• 英文别名: 2-(4,5-Dihexyl-2-iodophenyl)ethynyl-trimethylsilane
• CAS: 155259-17-9
• 化学式: C₂₃H₃₇ISi
• 分子量: 468.537
• InChiKey: JJYROKVYJMOVIS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.77
• 重原子数：
  25
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 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：

  2-((trimethylsilyl)ethynyl)-4,5-dihexyl-1-iodobenzene 在 bis-triphenylphosphine-palladium(II) chloride 氢氧化钾 、 copper(l) iodide 、 四甲基乙二胺 、 氧气 、 二异丙胺 、 copper(l) chloride 作用下， 以 四氢呋喃 、 甲醇 、 邻二氯苯 为溶剂， 反应 0.5h， 生成 2,2'-bis((trimethylsilyl)ethynyl)-4,4',5,5'-tetrahexyldiphenyldiacetylene
  参考文献：
  名称：

  Synthesis of Diacetylene Macrocycles Derived from 1,2-Diethynyl Benzene Derivatives: Structure and Reactivity of the Strained Cyclic Dimer

  摘要：

  Diacetylene macrocycles 2-4 (n = 1-3) (R = H, C4H9, C6H13, C10H21, C12H25, OC10H21) have been prepared from the oxidative coupling of 1,2-diethynylbenzene derivatives. These compounds can be produced in useful quantities and are of interest as precursors to novel conjugated organic polymers. The reported results indicate that when the R groups are large the dimeric macrocycle (n = 1) can be prepared in as high as 74% yield from the corresponding 1,2-diethynylbenzene in a one-step procedure. An alternate multistep procedure was found to produce the tetrameric macrocycle (n = 3, R = C6H13) in 45 % yield. The highly strained dimeric macrocycle was characterized by an X-ray structure and was found to be very reactive. The dimers undergo a rapid very exothermic polymerization at 100-125-degrees-C, indicative of a chain reaction. Reaction of the dimeric macrocycles with iodine results in intramolecular cyclization and a new 20pi electron tetraiodide fused ring system. Reaction of the tetraiodide with oxygen produces a related compound in which two of the iodides have been converted to ketones.

  DOI：

  10.1021/jo00085a016
• 作为产物：
  描述：

  1,2-二己基-苯 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 sodium iodate 、 硫酸 、 碘 、 二异丙胺 作用下， 以 溶剂黄146 为溶剂， 生成 2-((trimethylsilyl)ethynyl)-4,5-dihexyl-1-iodobenzene
  参考文献：
  名称：

  Synthesis of Diacetylene Macrocycles Derived from 1,2-Diethynyl Benzene Derivatives: Structure and Reactivity of the Strained Cyclic Dimer

  摘要：

  Diacetylene macrocycles 2-4 (n = 1-3) (R = H, C4H9, C6H13, C10H21, C12H25, OC10H21) have been prepared from the oxidative coupling of 1,2-diethynylbenzene derivatives. These compounds can be produced in useful quantities and are of interest as precursors to novel conjugated organic polymers. The reported results indicate that when the R groups are large the dimeric macrocycle (n = 1) can be prepared in as high as 74% yield from the corresponding 1,2-diethynylbenzene in a one-step procedure. An alternate multistep procedure was found to produce the tetrameric macrocycle (n = 3, R = C6H13) in 45 % yield. The highly strained dimeric macrocycle was characterized by an X-ray structure and was found to be very reactive. The dimers undergo a rapid very exothermic polymerization at 100-125-degrees-C, indicative of a chain reaction. Reaction of the dimeric macrocycles with iodine results in intramolecular cyclization and a new 20pi electron tetraiodide fused ring system. Reaction of the tetraiodide with oxygen produces a related compound in which two of the iodides have been converted to ketones.

  DOI：

  10.1021/jo00085a016

文献信息

• Redox-switchable Intramolecular<i>π−π</i>-Stacking of Perylene Bisimide Dyes in a Cyclophane
  作者：Felix Schlosser、Michael Moos、Christoph Lambert、Frank Würthner

  DOI：10.1002/adma.201201266

  日期：2013.1.18

  Molecular actuation by stepwise electrochemical reduction is demonstrated for a cyclophane that exhibits a pronounced conformational transition from a closed cavity with cofacially stacked PBIs in the neutral state to an expanded open cavity in the three‐ and fourfold reduced state.

  已证明，通过逐步电化学还原的分子致动环烯具有明显的构象过渡，该闭合构象从具有中性状态的界面堆叠的PBI的封闭腔到三倍和四倍还原态的扩展开腔。
• Zhou Qin, Carroll Patrick J., Swager Timothy M., J. Org. Chem., 59 (1994) N 6, S 1294-1301
  作者：Zhou Qin, Carroll Patrick J., Swager Timothy M.

  DOI：——

  日期：——