3-(4-chlorophenyl)-7-hydroxymethyl-4,6-dimethoxyindole | 870193-26-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 3-(4-chlorophenyl)-7-hydroxymethyl-4,6-dimethoxyindole
• 英文别名: [3-(4-chlorophenyl)-4,6-dimethoxy-1H-indol-7-yl]methanol
• CAS: 870193-26-3
• 化学式: C₁₇H₁₆ClNO₃
• 分子量: 317.772
• InChiKey: UYGGRKVJPMCFSW-UHFFFAOYSA-N

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：

  3-(4-chlorophenyl)-7-hydroxymethyl-4,6-dimethoxyindole 在 溶剂黄146 、 三氯氧磷 作用下， 以 苯 为溶剂， 反应 14.67h， 生成 4,28-di-(4-chlorophenyl)-6,8,30,32-tetramethoxy-11,18,25,34,35-pentaazaheptacyclo[25.5.2.2^3,9.0^5,36.0^12,17.0^19,24.0^29,33]hexatriacontane-1(32),3,5(36),6,8,10,12,14,16,19,21,23,25,27,29(33),30-hexadecaene
  参考文献：
  名称：

  Synthesis and utilisation of 2,7′-diindolylmethanes and a 2-(2-indolyl)pyrrolylmethane as macrocyclic precursors

  摘要：

  Treatment of 3-(4-chlorophenyl)-7-hydroxymethyl-4,6-dimethoxyindole with 3-(4-chlorophenyl)-4,6-dimethoxyindole results in the generation of two geometrically isomeric diindolylmethanes in addition to a novel triindolyl oligomer, which has been structurally characterised. The 2,7'-diindolylmethanes were found to be unstable under Vilsmeier formylation conditions, thus hampering macrocyle precursor construction. In an alternate approach, the 3-(4-chlorophenyl)-4,6-dimethoxyindole-7-carbaidehyde was converted into the indolyl-pyrrolyl macrocycle precursor 5-(3-(4-chlorophenyl)-4,6-dimethoxyindole-2-ylmethyl)-4-ethyl-3-methylpyrrole-2,7-dicarbaldehyde, which was used to generate an unsymmetrical pentaaza macrocycle. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.08.075
• 作为产物：
  描述：

  3-(4-chlorophenyl)-4,6-dimethoxyindole 在 sodium tetrahydroborate 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 3-(4-chlorophenyl)-7-hydroxymethyl-4,6-dimethoxyindole
  参考文献：
  名称：

  Synthesis and utilisation of 2,7′-diindolylmethanes and a 2-(2-indolyl)pyrrolylmethane as macrocyclic precursors

  摘要：

  Treatment of 3-(4-chlorophenyl)-7-hydroxymethyl-4,6-dimethoxyindole with 3-(4-chlorophenyl)-4,6-dimethoxyindole results in the generation of two geometrically isomeric diindolylmethanes in addition to a novel triindolyl oligomer, which has been structurally characterised. The 2,7'-diindolylmethanes were found to be unstable under Vilsmeier formylation conditions, thus hampering macrocyle precursor construction. In an alternate approach, the 3-(4-chlorophenyl)-4,6-dimethoxyindole-7-carbaidehyde was converted into the indolyl-pyrrolyl macrocycle precursor 5-(3-(4-chlorophenyl)-4,6-dimethoxyindole-2-ylmethyl)-4-ethyl-3-methylpyrrole-2,7-dicarbaldehyde, which was used to generate an unsymmetrical pentaaza macrocycle. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.08.075

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.
• Synthesis and utilisation of 2,7′-diindolylmethanes and a 2-(2-indolyl)pyrrolylmethane as macrocyclic precursors
  作者：Paul K. Bowyer、David StC. Black、Donald C. Craig

  DOI：10.1016/j.tet.2005.08.075

  日期：2005.11

  Treatment of 3-(4-chlorophenyl)-7-hydroxymethyl-4,6-dimethoxyindole with 3-(4-chlorophenyl)-4,6-dimethoxyindole results in the generation of two geometrically isomeric diindolylmethanes in addition to a novel triindolyl oligomer, which has been structurally characterised. The 2,7'-diindolylmethanes were found to be unstable under Vilsmeier formylation conditions, thus hampering macrocyle precursor construction. In an alternate approach, the 3-(4-chlorophenyl)-4,6-dimethoxyindole-7-carbaidehyde was converted into the indolyl-pyrrolyl macrocycle precursor 5-(3-(4-chlorophenyl)-4,6-dimethoxyindole-2-ylmethyl)-4-ethyl-3-methylpyrrole-2,7-dicarbaldehyde, which was used to generate an unsymmetrical pentaaza macrocycle. (c) 2005 Elsevier Ltd. All rights reserved.