7-hydroxymethyl-3-(4'-bromophenyl)-4,6-dimethoxyindole | 151320-92-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 7-hydroxymethyl-3-(4'-bromophenyl)-4,6-dimethoxyindole
• 英文别名: [3-(4-bromophenyl)-4,6-dimethoxy-1H-indol-7-yl]methanol
• CAS: 151320-92-2
• 化学式: C₁₇H₁₆BrNO₃
• 分子量: 362.223
• InChiKey: WNYKVVOYLAOPSD-UHFFFAOYSA-N

物化性质

• 沸点：
  569.5±50.0 °C(Predicted)
• 密度：
  1.477±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  54.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-hydroxymethyl-3-(4'-bromophenyl)-4,6-dimethoxyindole 在 对甲苯磺酸 、 溶剂黄146 作用下， 以60%的产率得到
  参考文献：
  名称：

  Calix[3]indoles, new macrocyclic tris(indolylmethylene) compounds with 2,7-linkages

  摘要：

  一系列大环三(吲哚亚甲基)化合物（钙[3]吲哚）可从 7-或 2-羟甲基吲哚或从吲哚与双(羟甲基)-2,7′-二吲哚亚甲基或双(羟甲基)吲哚与 2,7′-二吲哚亚甲基的组合中获得；一种吲哚与一种双(羟甲基)-2,2′-二吲哚甲烷结合可得到异构系列。

  DOI：

  10.1039/c39930000819
• 作为产物：
  描述：

  3-(4-bromophenyl)-4,6-dimethoxyindole-7-carbaldehyde 在 sodium tetrahydroborate 作用下， 生成 7-hydroxymethyl-3-(4'-bromophenyl)-4,6-dimethoxyindole
  参考文献：
  名称：

  Calix[3]indoles, new macrocyclic tris(indolylmethylene) compounds with 2,7-linkages

  摘要：

  一系列大环三(吲哚亚甲基)化合物（钙[3]吲哚）可从 7-或 2-羟甲基吲哚或从吲哚与双(羟甲基)-2,7′-二吲哚亚甲基或双(羟甲基)吲哚与 2,7′-二吲哚亚甲基的组合中获得；一种吲哚与一种双(羟甲基)-2,2′-二吲哚甲烷结合可得到异构系列。

  DOI：

  10.1039/c39930000819

文献信息

• Calix[4]indoles: New Macrocyclic Tetra(indolylmethylene) Compounds with 2,7-Linkages
  作者：David StC. Black、Donald C. Craig、Naresh Kumar

  DOI：10.1016/0040-4039(95)01516-k

  日期：1995.10

  Some 7-hydroxymethyl-3-aryl-4,6-dimethoxyindoles 1 undergo acid catalysed cyclotetramerisation in addition to cyclotrimerisation to give the calix[4]indoles 3 as well as the calix[3]indoles 2: me tetramers 3, which display a 1,3-alternate cube-like structure, can also be obtained by the acid catalysed dimerisation of 7-hydroxymethyl-2,7'-dindolylmethanes 7.
• Triindolyl Macrocycle as a Molecular Platform in the Synthesis of Sumanene-Containing Polyphenols
  作者：A. Ya. Vainer、K. M. Dyumaev、A. M. Kovalenko、N. V. Barannik、S. Ya. Zelenetskaya、K. I. Zelikson、S. V. Kotov

  DOI：10.1134/s0012500818090057

  日期：2018.9

  A new strategy has been suggested for the synthesis of sumanene-containing polyphenols chemically bound to a molecular platform based on the triindolyl macrocycle. The initial assembly has been obtained by the Suzuki-Miyaura reaction of a bromo-containing indolyl macrocycle and boryl derivative of N,N'-disumanenylaniline. Subsequent benzylation with 3,5-dimethoxybenzyl bromide, exhaustive demethylation of the modified macrocycle, and partial blocking of the corresponding phenolic hydroxyls by two different acid-labile protective groups have led to the formation of the target polyphenol containing sumanene fragments. The obtained polyphenol has allowed us to develop on its basis a new positive resist for electronbeam nanolithography. This resist can realize topological structures with resolution of 9-12 nm.