dotriaconta-15,17-diyn-1,32-diol | 1100884-59-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: dotriaconta-15,17-diyn-1,32-diol
• 英文别名: dotriaconta-15,17-diyne-1,32-diol
• CAS: 1100884-59-0
• 化学式: C₃₂H₅₈O₂
• 分子量: 474.811
• InChiKey: UJLPEMCPSYCIDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.5
• 重原子数：
  34
• 可旋转键数：
  27
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  dotriaconta-15,17-diyn-1,32-diol 在 三乙胺 作用下， 以 乙醇 、 氯仿 、 乙腈 为溶剂， 反应 73.0h， 生成 dotriaconta-15,17-diyn-1,32-diylbis[2-(dimethylammonio)ethylphosphate]
  参考文献：
  名称：

  Synthesis of novel symmetrical, single-chain, diacetylene-modified bolaamphiphiles with different alkyl chain lengths

  摘要：

  General syntheses of novel symmetrical, single-chain, diacetylene-modified bolaphospholipids have been carried out in five steps. For the omega-alkynols, which have an important role as key intermediates, three different synthetic approaches were comprehensively investigated. For the final synthesis it is suggested that (1) alkylation of lithium (trimethylsilyl)acetylide with tetrahydropyranyl-protected omega-bromoalcohols, followed by (2) cleavage of the trimethylsilyl moiety and the tetrahydropyranyl protecting group, and (3) copper(II)-catalyzed Eglinton coupling is the best strategy for obtaining diacetylene-modified alkane-1,omega-diols, because higher yields were obtained while avoiding the formation of by-products. Moreover, conversion of the diols into bipolar phospholipids was achieved by bis-phosphorylation with beta-bromoethylphosphoric acid dichloride and subsequent quaternization with trimethylamine or dimethylamine. Finally, spectral data are presented for novel single-chain, diacetylene-modified bolaphospholipids with promising potential as starting molecules in the formation of polymerizable and, thus, thermostable nanofibers.

  DOI：

  10.1007/s00706-010-0255-y
• 作为产物：
  描述：

  1-十五炔 在 吡啶 、 乙基氯化镁 、 copper(II) acetate monohydrate 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 邻苯二甲酸二烯丙酯 为溶剂， 反应 41.0h， 生成 dotriaconta-15,17-diyn-1,32-diol
  参考文献：
  名称：

  Synthesis of novel symmetrical, single-chain, diacetylene-modified bolaamphiphiles with different alkyl chain lengths

  摘要：

  General syntheses of novel symmetrical, single-chain, diacetylene-modified bolaphospholipids have been carried out in five steps. For the omega-alkynols, which have an important role as key intermediates, three different synthetic approaches were comprehensively investigated. For the final synthesis it is suggested that (1) alkylation of lithium (trimethylsilyl)acetylide with tetrahydropyranyl-protected omega-bromoalcohols, followed by (2) cleavage of the trimethylsilyl moiety and the tetrahydropyranyl protecting group, and (3) copper(II)-catalyzed Eglinton coupling is the best strategy for obtaining diacetylene-modified alkane-1,omega-diols, because higher yields were obtained while avoiding the formation of by-products. Moreover, conversion of the diols into bipolar phospholipids was achieved by bis-phosphorylation with beta-bromoethylphosphoric acid dichloride and subsequent quaternization with trimethylamine or dimethylamine. Finally, spectral data are presented for novel single-chain, diacetylene-modified bolaphospholipids with promising potential as starting molecules in the formation of polymerizable and, thus, thermostable nanofibers.

  DOI：

  10.1007/s00706-010-0255-y

文献信息

• Synthesis of unsymmetrical saturated or diacetylenic cationic bolaamphiphiles
  作者：Mathieu Berchel、Loïc Lemiègre、Sylvain Trépout、Olivier Lambert、Jelena Jeftić、Thierry Benvegnu

  DOI：10.1016/j.tetlet.2008.10.073

  日期：2008.12

  This work presents the synthesis of novel unsymmetrical bolaamphiphiles bearing a sugar residue and a cationic glycine betaine moiety connected to both ends of a C-22 or C-32 oligomethylene bridging chain possessing or not a diacetylenic unit. Preliminary transmission electron microscopy (TEM) studies revealed the polymorphism of these bola lipids with regard to their self-assembled morphologies in water depending on the presence or not of the diacetylenic functionality and on alkyl chain length. (C) 2008 Elsevier Ltd, All rights reserved.