tetratriaconta-16,18-diyn-1,34-diol | 1231774-88-1

• 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: tetratriaconta-16,18-diyn-1,34-diol
• 英文别名: tetratriaconta-16,18-diyne-1,34-diol
• CAS: 1231774-88-1
• 化学式: C₃₄H₆₂O₂
• 分子量: 502.865
• InChiKey: DUYBOIZXPOWGBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.6
• 重原子数：
  36
• 可旋转键数：
  29
• 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：

  tetratriaconta-16,18-diyn-1,34-diol 在 三乙胺 作用下， 以 乙醇 、 氯仿 、 乙腈 为溶剂， 反应 73.0h， 生成 tetratriaconta-16,18-diyn-1,34-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：

  16-heptadecyn-1-ol 在 copper(II) acetate monohydrate 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以60%的产率得到tetratriaconta-16,18-diyn-1,34-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