5-(hydroxymethyl)-1,3-phenylene-16-crown-5 | 191211-55-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(hydroxymethyl)-1,3-phenylene-16-crown-5
• 英文别名: 2,5,8,11,14-Pentaoxabicyclo[13.3.1]nonadeca-1(19),15,17-trien-17-ylmethanol
• CAS: 191211-55-9
• 化学式: C₁₅H₂₂O₆
• 分子量: 298.336
• InChiKey: PTYNOQODGKGHMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-(hydroxymethyl)-1,3-phenylene-16-crown-5 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以85%的产率得到2,5,8,11,14-Pentaoxa-bicyclo[13.3.1]nonadeca-1(18),15(19),16-triene-17-carbaldehyde
  参考文献：
  名称：

  Syntheses of Monofunctional Derivatives of m-Phenylene-16-crown-5, Bis(m-phenylene)-32-crown-10, and m-Phenylene-p-phenylene-33-crown-10

  摘要：

  A series of monofunctional bis(m-phenylene)-32-crown-10 and m-phenylene-p-phenylene-33-crown-10 derivatives has been synthesized. Cyclization of m- and p-bis(omega-chlorotetraethyleneoxy)benzenes (6) with 5-substituted resorcinols 1 using pseudo-high dilution conditions in DMF and either CsF or K2CO3 as base afforded 5-carbomethoxy-1,3-phenylene-m-phenylene-32-crown-10 (7a, 46%), 5-carbomethoxy-1,3-phenylene-p-phenylene-33-crown-10 (7b, 48%), 5-(benzyloxy)-1,3-phenylen-m-phenylene-32-crown-10 (11b, 51%). Unsubstituted m-phenylene-p-phenylene-33-crown-10 (15) was also made (29%) in this way. Functional group conversions of the bis-phenylene macrocycles yielded 5-carboxy-1,3-phenylene-m-phenylene-32-crown-10 (8a), 5-(hydroxymethyl)-1,3-phenylene-m-phenylene-32-crawn-10 (9a), 5-(bromomethyl)-1,3-phenylene-m-phenylene-32-crown-10 (10a), 5-hydroxy-1,3-phenylene-m-phenylene-32-crown-10 (12a), 5-hydroxy-1,3-phenylene-p-phenylene-33-crown-10 (12b), 5-(phthalimidomethyl)-1,3-phenylene-m-phenylene-32-crown-10 (13a), and 5-(aminomethyl)-1,3-phenylene-m-phenylene-32-crown-10 (14a). Similarly 5-carbomethoxy-1,3-phenylene-16-crown-5 (4) was transformed to the corresponding acid (16), hydroxymethyl (17), formyl(18), bromomethyl (19), phthalimidomethyl (20), azidomethyl (21), and aminomethyl (22) derivatives. These compounds are building blocks for supramolecular assemblies (as shown by the synthesis of a Schiff base (23) from 18 and a diester (24) from 4,4'-biphenol and 17) and useful endcapping or pendant host components of macromolecules.

  DOI：

  10.1021/jo9619948
• 作为产物：
  描述：

  Methyl 2,5,8,11,14-pentaoxabicyclo[13.3.1]nonadeca-1(19),15,17-triene-17-carboxylate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到5-(hydroxymethyl)-1,3-phenylene-16-crown-5
  参考文献：
  名称：

  Syntheses of Monofunctional Derivatives of m-Phenylene-16-crown-5, Bis(m-phenylene)-32-crown-10, and m-Phenylene-p-phenylene-33-crown-10

  摘要：

  A series of monofunctional bis(m-phenylene)-32-crown-10 and m-phenylene-p-phenylene-33-crown-10 derivatives has been synthesized. Cyclization of m- and p-bis(omega-chlorotetraethyleneoxy)benzenes (6) with 5-substituted resorcinols 1 using pseudo-high dilution conditions in DMF and either CsF or K2CO3 as base afforded 5-carbomethoxy-1,3-phenylene-m-phenylene-32-crown-10 (7a, 46%), 5-carbomethoxy-1,3-phenylene-p-phenylene-33-crown-10 (7b, 48%), 5-(benzyloxy)-1,3-phenylen-m-phenylene-32-crown-10 (11b, 51%). Unsubstituted m-phenylene-p-phenylene-33-crown-10 (15) was also made (29%) in this way. Functional group conversions of the bis-phenylene macrocycles yielded 5-carboxy-1,3-phenylene-m-phenylene-32-crown-10 (8a), 5-(hydroxymethyl)-1,3-phenylene-m-phenylene-32-crawn-10 (9a), 5-(bromomethyl)-1,3-phenylene-m-phenylene-32-crown-10 (10a), 5-hydroxy-1,3-phenylene-m-phenylene-32-crown-10 (12a), 5-hydroxy-1,3-phenylene-p-phenylene-33-crown-10 (12b), 5-(phthalimidomethyl)-1,3-phenylene-m-phenylene-32-crown-10 (13a), and 5-(aminomethyl)-1,3-phenylene-m-phenylene-32-crown-10 (14a). Similarly 5-carbomethoxy-1,3-phenylene-16-crown-5 (4) was transformed to the corresponding acid (16), hydroxymethyl (17), formyl(18), bromomethyl (19), phthalimidomethyl (20), azidomethyl (21), and aminomethyl (22) derivatives. These compounds are building blocks for supramolecular assemblies (as shown by the synthesis of a Schiff base (23) from 18 and a diester (24) from 4,4'-biphenol and 17) and useful endcapping or pendant host components of macromolecules.

  DOI：

  10.1021/jo9619948