pentacos-2-yn-1-ol | 499138-63-5

• 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: pentacos-2-yn-1-ol
• 英文别名: Pentacos-2-yn-1-ol
• CAS: 499138-63-5
• 化学式: C₂₅H₄₈O
• 分子量: 364.656
• InChiKey: JWPQJJSYPVGRLI-UHFFFAOYSA-N

物化性质

• 熔点：
  70 °C
• 沸点：
  311.1±10.0 °C(Predicted)
• 密度：
  0.864±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.4
• 重原子数：
  26
• 可旋转键数：
  20
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  pentacos-2-yn-1-ol 在 bis-triphenylphosphine-palladium(II) chloride 哌啶 、 copper(l) iodide 、 偶氮二甲酸二异丙酯 、 potassium tert-butylate 、 lithium 、 1,3-丙二胺 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 生成 3,5-dimethyl-4-{25-[4-(2-triisopropylsilylethynyl)phenyl]pentacos-24-yn-1-yloxy}-1-iodobenzene
  参考文献：
  名称：

  An Efficient Synthesis of Liquid Crystalline Gigantocycles Combining Banana-Shaped and Rod-Like Mesogenic Units

  摘要：

  The synthesis of monodisperse gigantocycles with 63, 87, and 147 ring atoms on the gram scale is described. These molecules were assembled from terphenylene derivatives and long, flexible chains which were mainly aliphatic, with I terminal alkyne groups. The latter allowed for ring formation through oxidative alkyne dimerization in high yield (80-87%). The combination of a rod-like and a banana-shaped mesogen connected by flexible chains within the backbone of a ring gives rise to nematic and smectic mesophases.

  DOI：

  10.1002/1521-3765(20021115)8:22<5094::aid-chem5094>3.0.co;2-6
• 作为产物：
  描述：

  1-溴二十二烷 在 正丁基锂 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 正己烷 为溶剂， 反应 22.5h， 生成 pentacos-2-yn-1-ol
  参考文献：
  名称：

  An Efficient Synthesis of Liquid Crystalline Gigantocycles Combining Banana-Shaped and Rod-Like Mesogenic Units

  摘要：

  The synthesis of monodisperse gigantocycles with 63, 87, and 147 ring atoms on the gram scale is described. These molecules were assembled from terphenylene derivatives and long, flexible chains which were mainly aliphatic, with I terminal alkyne groups. The latter allowed for ring formation through oxidative alkyne dimerization in high yield (80-87%). The combination of a rod-like and a banana-shaped mesogen connected by flexible chains within the backbone of a ring gives rise to nematic and smectic mesophases.

  DOI：

  10.1002/1521-3765(20021115)8:22<5094::aid-chem5094>3.0.co;2-6

文献信息

• Synthesis of novel symmetrical, single-chain, diacetylene-modified bolaamphiphiles with different alkyl chain lengths
  作者：Simon Drescher、Katrin Helmis、Andreas Langner、Bodo Dobner

  DOI：10.1007/s00706-010-0255-y

  日期：2010.3

  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.
• An Efficient Synthesis of Liquid Crystalline Gigantocycles Combining Banana-Shaped and Rod-Like Mesogenic Units
  作者：Adelheid Godt、Stefan Duda、Ömer Ünsal、Jürgen Thiel、Alice Härter、Mark Roos、Carsten Tschierske、Siegmar Diele

  DOI：10.1002/1521-3765(20021115)8:22<5094::aid-chem5094>3.0.co;2-6

  日期：2002.11.15

  The synthesis of monodisperse gigantocycles with 63, 87, and 147 ring atoms on the gram scale is described. These molecules were assembled from terphenylene derivatives and long, flexible chains which were mainly aliphatic, with I terminal alkyne groups. The latter allowed for ring formation through oxidative alkyne dimerization in high yield (80-87%). The combination of a rod-like and a banana-shaped mesogen connected by flexible chains within the backbone of a ring gives rise to nematic and smectic mesophases.