3,7,9,22,24-Pentamethyl-11,14,17,20-tetraoxa-3-azatricyclo[19.4.0.05,10]pentacosa-1(25),5,7,9,21,23-hexaene | 1178550-41-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,7,9,22,24-Pentamethyl-11,14,17,20-tetraoxa-3-azatricyclo[19.4.0.05,10]pentacosa-1(25),5,7,9,21,23-hexaene
• 英文别名: 3,7,9,22,24-pentamethyl-11,14,17,20-tetraoxa-3-azatricyclo[19.4.0.05,10]pentacosa-1(25),5,7,9,21,23-hexaene
• CAS: 1178550-41-8
• 化学式: C₂₅H₃₅NO₄
• 分子量: 413.557
• InChiKey: XTQAHTBKIBLANJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  30
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  40.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1,2-bis(2-tosylethoxy)ethane 、 bis-(2-hydroxy-3,5-dimethyl-benzyl)-methyl-amine 在 sodium hydroxide 作用下， 以 乙腈 为溶剂， 反应 72.0h， 以80%的产率得到3,7,9,22,24-Pentamethyl-11,14,17,20-tetraoxa-3-azatricyclo[19.4.0.05,10]pentacosa-1(25),5,7,9,21,23-hexaene
  参考文献：
  名称：

  Selective crown ether based macrocyclization: a model case study from N,N-bis(2-hydroxyalkylbenzyl)alkylamine

  摘要：

  A model case of selective crown ether based macrocycles, i.e., [1+1] or [2+2] macrocycles, obtained from a simple reaction of N,N-bis(2-hydroxyalkylbenzyl)alkylamine, HBA, and ditosylated compounds is proposed. For HBA with the methyl group at ortho and para positions, and at N atom, 1, the reaction between this derivative and the ditosylated compound with three, four, five, or eight atom chain length gives only a [1+1] macrocycle. For HBA with the methyl group at ortho and para positions, but a cyclohexyl group at N atom, 2, the reaction gives both [1+1] and [2+2] macrocyclic types when reacting with the ditosylated compound. The present work indicates that the structure of HBA induces selective macrocyclization to provide both [1+1] and [2+2] macrocycles. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.04.093

文献信息

• Selective crown ether based macrocyclization: a model case study from N,N-bis(2-hydroxyalkylbenzyl)alkylamine
  作者：Suwabun Chirachanchai、Thitiporn Rungsimanon、Suttinun Phongtamrug、Mikiji Miyata、Apirat Laobuthee

  DOI：10.1016/j.tet.2009.04.093

  日期：2009.7

  A model case of selective crown ether based macrocycles, i.e., [1+1] or [2+2] macrocycles, obtained from a simple reaction of N,N-bis(2-hydroxyalkylbenzyl)alkylamine, HBA, and ditosylated compounds is proposed. For HBA with the methyl group at ortho and para positions, and at N atom, 1, the reaction between this derivative and the ditosylated compound with three, four, five, or eight atom chain length gives only a [1+1] macrocycle. For HBA with the methyl group at ortho and para positions, but a cyclohexyl group at N atom, 2, the reaction gives both [1+1] and [2+2] macrocyclic types when reacting with the ditosylated compound. The present work indicates that the structure of HBA induces selective macrocyclization to provide both [1+1] and [2+2] macrocycles. (C) 2009 Elsevier Ltd. All rights reserved.