2,2'',6,6''-tetrakis(hydroxymethyl)-1,1':3',1''-terphenyl | 139896-54-1

• 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: 2,2'',6,6''-tetrakis(hydroxymethyl)-1,1':3',1''-terphenyl
• 英文别名: (6,2'',6''-Tris-hydroxymethyl-(1,1',3',1'')terphenyl-2-YL)-methanol；[2-[3-[2,6-bis(hydroxymethyl)phenyl]phenyl]-3-(hydroxymethyl)phenyl]methanol
• CAS: 139896-54-1
• 化学式: C₂₂H₂₂O₄
• 分子量: 350.414
• InChiKey: HVASWYBPCAVSMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  80.9
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2'',6,6''-tetrakis(hydroxymethyl)-1,1':3',1''-terphenyl 、 二乙二醇双对甲苯磺酸酯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以16%的产率得到hexaoxacyclophane
  参考文献：
  名称：

  Oxacyclophanes based on a m-terphenyl framework

  摘要：

  m-Terphenyl tetraphenol 4 (Scheme I) and tetrabenzyl alcohol 19 (Scheme IV) were efficiently synthesized from 2,6-dichloroiodobenzene and an appropriate aryl Grignard, using tandem aryne technology. Each tetrol was used to construct bicyclic oxacyclophanes by linking the 3,3" and 5,5" substituents with bis-alkylating or acylating agents. Examples are 7, 14, 15, and 20-24. Only the meta isomer of xylylene dichloride formed a bicyclic oxacyclophane with 4; the ortho and para isomers gave polymers. However all three isomers gave oxacyclophanes (i.e., 10-12) with the diphenol 9 (only one link across the m-terphenyl framework) and bicyclic oxacyclophanes with 19 (i.e., 20-22), where each link contains two additional atoms. Para-linked 12 and 21 show restricted rotation of the p-xylylene rings. Two noninterconvertible conformers were obtained when the m-xylylene linking group contained a vicinal methoxy substituent (i.e., 15uu and 15ud).

  DOI：

  10.1021/jo00035a034
• 作为产物：
  描述：

  2,2'',6,6''-tetraformyl-1,1':3',1''-terphenyl 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 16.0h， 以98%的产率得到2,2'',6,6''-tetrakis(hydroxymethyl)-1,1':3',1''-terphenyl
  参考文献：
  名称：

  Oxacyclophanes based on a m-terphenyl framework

  摘要：

  m-Terphenyl tetraphenol 4 (Scheme I) and tetrabenzyl alcohol 19 (Scheme IV) were efficiently synthesized from 2,6-dichloroiodobenzene and an appropriate aryl Grignard, using tandem aryne technology. Each tetrol was used to construct bicyclic oxacyclophanes by linking the 3,3" and 5,5" substituents with bis-alkylating or acylating agents. Examples are 7, 14, 15, and 20-24. Only the meta isomer of xylylene dichloride formed a bicyclic oxacyclophane with 4; the ortho and para isomers gave polymers. However all three isomers gave oxacyclophanes (i.e., 10-12) with the diphenol 9 (only one link across the m-terphenyl framework) and bicyclic oxacyclophanes with 19 (i.e., 20-22), where each link contains two additional atoms. Para-linked 12 and 21 show restricted rotation of the p-xylylene rings. Two noninterconvertible conformers were obtained when the m-xylylene linking group contained a vicinal methoxy substituent (i.e., 15uu and 15ud).

  DOI：

  10.1021/jo00035a034

文献信息

• Oxacyclophanes based on a m-terphenyl framework
  作者：Rupinder S. Grewal、Harold Hart、Thottumkara K. Vinod

  DOI：10.1021/jo00035a034

  日期：1992.4

  m-Terphenyl tetraphenol 4 (Scheme I) and tetrabenzyl alcohol 19 (Scheme IV) were efficiently synthesized from 2,6-dichloroiodobenzene and an appropriate aryl Grignard, using tandem aryne technology. Each tetrol was used to construct bicyclic oxacyclophanes by linking the 3,3" and 5,5" substituents with bis-alkylating or acylating agents. Examples are 7, 14, 15, and 20-24. Only the meta isomer of xylylene dichloride formed a bicyclic oxacyclophane with 4; the ortho and para isomers gave polymers. However all three isomers gave oxacyclophanes (i.e., 10-12) with the diphenol 9 (only one link across the m-terphenyl framework) and bicyclic oxacyclophanes with 19 (i.e., 20-22), where each link contains two additional atoms. Para-linked 12 and 21 show restricted rotation of the p-xylylene rings. Two noninterconvertible conformers were obtained when the m-xylylene linking group contained a vicinal methoxy substituent (i.e., 15uu and 15ud).