triaconta-14,16-diyn-1,30-diol | 1231774-87-0

• 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: triaconta-14,16-diyn-1,30-diol
• 英文别名: triaconta-14,16-diyne-1,30-diol
• CAS: 1231774-87-0
• 化学式: C₃₀H₅₄O₂
• 分子量: 446.758
• InChiKey: YIQQAVHXMGTDMD-UHFFFAOYSA-N

物化性质

• 熔点：
  93 °C(Solvent: Ligroine)
• 沸点：
  582.4±15.0 °C(predicted)
• 密度：
  0.920±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.4
• 重原子数：
  32
• 可旋转键数：
  25
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 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：

  triaconta-14,16-diyn-1,30-diol 在 三乙胺 作用下， 以 乙醇 、 氯仿 、 乙腈 为溶剂， 反应 73.0h， 生成 triaconta-14,16-diyn-1,30-diylbis[2-(trimethylammonio)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：

  14-十五炔-1-醇 在 吡啶 、 copper(II) acetate monohydrate 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以30%的产率得到triaconta-14,16-diyn-1,30-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