1-hexoxy-3-iodo-5[(trimethylsilyl)ethynyl]benzene | 144001-29-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-hexoxy-3-iodo-5[(trimethylsilyl)ethynyl]benzene
• 英文别名: 2-(3-Hexoxy-5-iodophenyl)ethynyl-trimethylsilane
• CAS: 144001-29-6
• 化学式: C₁₇H₂₅IOSi
• 分子量: 400.375
• InChiKey: MMMWVPVZWLYVAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.48
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-hexoxy-3-iodo-5[(trimethylsilyl)ethynyl]benzene 、 3-bromo-5-(hexyloxy)benzenediazonium tetrafluoroborate 、 三甲基乙炔基硅 生成 [3-Hexyloxy-5-(3-hexyloxy-5-iodo-phenylethynyl)-phenylethynyl]-trimethyl-silane
  参考文献：
  名称：

  Solid-Phase Synthesis of Phenylacetylene Oligomers Utilizing a Novel 3-Propyl-3-(benzyl-supported) Triazene Linkage

  摘要：

  Sequence-specific phenylacetylene oligomers consisting of functionalized monomers (hexyl benzoate, hexyl phenyl ether, benzonitrile, and tert-butylphenyl) are synthesized in gram quantities using solid-phase methods. Growing oligomers are attached to a divinylbenzene cross-linked polystyrene support by the 1-aryl-3-propyl-3-(benzyl-supported) triazene moiety. This linkage is obtained by reaction of arenediazonium tetrafluoroborate salts with a n-propylamino-modified Merrifield resin. Condensation strategies are described, producing oligomers with higher yields and simplified procedures compared to solution-phase methods. Terminal acetylene is protected with a trimethylsilyl group. After deprotection of the resin-bound terminal acetylene, an aryl iodide monomer or an aryl iodide-terminated oligomer is coupled to the supported oligomer using a palladium(0) catalyst. The cycle can be repeated to produce sequence-specific oligomers of varying length and functionality. The resulting oligomers are liberated from the polymer support by cleavage of the 1-aryl-3-propyl-3-(benzyl-supported) triazene group by reaction with iodomethane producing an aryl iodide.

  DOI：

  10.1021/jo961250u
• 作为产物：
  描述：

  3-Bromo-5-hexyloxy-phenylamine 在 copper(l) iodide 、 tris(dibenzylideneacetone)dipalladium (0) 、 三苯基膦 亚硝酸特丁酯 、 propylaminomethyl polystyrene: 1percent divinylbenzene copolymer 、 三氟化硼乙醚 、 potassium carbonate 、 碘甲烷 作用下， 以 四氢呋喃 为溶剂， 反应 72.67h， 生成 1-hexoxy-3-iodo-5[(trimethylsilyl)ethynyl]benzene
  参考文献：
  名称：

  Solid-Phase Synthesis of Phenylacetylene Oligomers Utilizing a Novel 3-Propyl-3-(benzyl-supported) Triazene Linkage

  摘要：

  Sequence-specific phenylacetylene oligomers consisting of functionalized monomers (hexyl benzoate, hexyl phenyl ether, benzonitrile, and tert-butylphenyl) are synthesized in gram quantities using solid-phase methods. Growing oligomers are attached to a divinylbenzene cross-linked polystyrene support by the 1-aryl-3-propyl-3-(benzyl-supported) triazene moiety. This linkage is obtained by reaction of arenediazonium tetrafluoroborate salts with a n-propylamino-modified Merrifield resin. Condensation strategies are described, producing oligomers with higher yields and simplified procedures compared to solution-phase methods. Terminal acetylene is protected with a trimethylsilyl group. After deprotection of the resin-bound terminal acetylene, an aryl iodide monomer or an aryl iodide-terminated oligomer is coupled to the supported oligomer using a palladium(0) catalyst. The cycle can be repeated to produce sequence-specific oligomers of varying length and functionality. The resulting oligomers are liberated from the polymer support by cleavage of the 1-aryl-3-propyl-3-(benzyl-supported) triazene group by reaction with iodomethane producing an aryl iodide.

  DOI：

  10.1021/jo961250u

文献信息

• Shape-Persistant Macrocycles with Terpyridine Units:  Synthesis, Characterization, and Structure in the Crystal
  作者：Christian Grave、Dieter Lentz、Andreas Schäfer、Paolo Samorì、Jürgen P. Rabe、Peter Franke、A. Dieter Schlüter

  DOI：10.1021/ja034029p

  日期：2003.6.1

  The synthesis of a variety of shape-persistent macrocycles with either one (1a-d, 2) or two (opposing) terpyridine units (3, 4, 5a-c) and inner diameters of up to 2 nm is described. The sequences are mainly based on transition metal cross-coupling reactions and, whenever appropriate, compared with one another regarding their respective efficiency. Typical overall yields and amounts prepared range from

  描述了具有一个 (1a-d, 2) 或两个 (相对的) 三联吡啶单元 (3, 4, 5a-c) 和内径高达 2 nm 的各种形状持久性大环的合成。这些序列主要基于过渡金属交叉偶联反应，并在适当的时候就它们各自的效率相互比较。典型的总产率和制备量范围分别为 8% (4) 至 27% (3) 和 25 mg (1a) 至 290 mg (1b)。对于目标循环的溶解性和加工，所有前体都已经用柔性侧链（己氧基或己氧基甲基）修饰。循环的表征基于 MALDI-TOF 质谱、2D 核磁共振光谱和/或低温单晶 X 射线衍射。它们在晶体中的堆积是根据侧链的数量和长度来讨论的。循环 1d 在溶液-HOPG 界面被物理吸附成有序结构，并通过扫描隧道显微镜 (STM) 进行研究。
• Solid-Phase Synthesis of Phenylacetylene Oligomers Utilizing a Novel 3-Propyl-3-(benzyl-supported) Triazene Linkage
  作者：James C. Nelson、James K. Young、Jeffrey S. Moore

  DOI：10.1021/jo961250u

  日期：1996.11.15

  Sequence-specific phenylacetylene oligomers consisting of functionalized monomers (hexyl benzoate, hexyl phenyl ether, benzonitrile, and tert-butylphenyl) are synthesized in gram quantities using solid-phase methods. Growing oligomers are attached to a divinylbenzene cross-linked polystyrene support by the 1-aryl-3-propyl-3-(benzyl-supported) triazene moiety. This linkage is obtained by reaction of arenediazonium tetrafluoroborate salts with a n-propylamino-modified Merrifield resin. Condensation strategies are described, producing oligomers with higher yields and simplified procedures compared to solution-phase methods. Terminal acetylene is protected with a trimethylsilyl group. After deprotection of the resin-bound terminal acetylene, an aryl iodide monomer or an aryl iodide-terminated oligomer is coupled to the supported oligomer using a palladium(0) catalyst. The cycle can be repeated to produce sequence-specific oligomers of varying length and functionality. The resulting oligomers are liberated from the polymer support by cleavage of the 1-aryl-3-propyl-3-(benzyl-supported) triazene group by reaction with iodomethane producing an aryl iodide.