1-O-benzyl 22-O-[3-hydroxy-2-(hydroxymethyl)-2-methylpropyl] (Z)-docos-11-enedioate | 850347-54-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-O-benzyl 22-O-[3-hydroxy-2-(hydroxymethyl)-2-methylpropyl] (Z)-docos-11-enedioate
• CAS: 850347-54-5
• 化学式: C₃₄H₅₆O₆
• 分子量: 560.815
• InChiKey: NCXWUCPYTPFXDO-IHWYPQMZSA-N

物化性质

• 沸点：
  628.1±40.0 °C(Predicted)
• 密度：
  1.025±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  40
• 可旋转键数：
  28
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-O-benzyl 22-O-[3-hydroxy-2-(hydroxymethyl)-2-methylpropyl] (Z)-docos-11-enedioate 在 palladium on activated charcoal 4-二甲氨基吡啶 、 lithium hydroxide 、 氢气 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 生成 docosanedioic acid mono-(2-tert-butoxycarbonylamino-1-undecanoyloxymethyl-ethyl) ester
  参考文献：
  名称：

  Design and Synthesis of Asymmetric Acyclic Phospholipid Bolaamphiphiles

  摘要：

  A synthetic route was devised for the generation of asymmetric lipid bolaamphiphiles through the sequential esterification of an alkyldioic acid, bearing distinct terminal protecting groups, with propanylamine and lyso-phosphatidylcholine headgroups. Bolaamphiphile self-assembly was investigated in solvent mixes of varying polarity by nuclear magnetic resonance (NMR) and Fourier transform-infrared (FT-IR) spectroscopy, as well as in water by cryo-high-resolution scanning electron microscopy (cryo-HRSEM). We anticipate that asymmetric lipid bolaamphiphiles will provide facile building blocks for engineering a variety of unique membrane-mimetic structures.

  DOI：

  10.1021/jo048167o
• 作为产物：
  描述：

  3-甲基-3-羟甲基氧杂环丁烷 在 4-二甲氨基吡啶 、 正丁基锂 、 三氟化硼乙醚 、 4-甲基苯磺酸吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 氯仿 、 甲苯 、 苯 为溶剂， 生成 1-O-benzyl 22-O-[3-hydroxy-2-(hydroxymethyl)-2-methylpropyl] (Z)-docos-11-enedioate
  参考文献：
  名称：

  Design and Synthesis of Asymmetric Acyclic Phospholipid Bolaamphiphiles

  摘要：

  A synthetic route was devised for the generation of asymmetric lipid bolaamphiphiles through the sequential esterification of an alkyldioic acid, bearing distinct terminal protecting groups, with propanylamine and lyso-phosphatidylcholine headgroups. Bolaamphiphile self-assembly was investigated in solvent mixes of varying polarity by nuclear magnetic resonance (NMR) and Fourier transform-infrared (FT-IR) spectroscopy, as well as in water by cryo-high-resolution scanning electron microscopy (cryo-HRSEM). We anticipate that asymmetric lipid bolaamphiphiles will provide facile building blocks for engineering a variety of unique membrane-mimetic structures.

  DOI：

  10.1021/jo048167o

文献信息

• Design and Synthesis of Asymmetric Acyclic Phospholipid Bolaamphiphiles
  作者：Toshitsugu Kai、Xue-Long Sun、Keith M. Faucher、Robert P. Apkarian、Elliot L. Chaikof

  DOI：10.1021/jo048167o

  日期：2005.4.1

  A synthetic route was devised for the generation of asymmetric lipid bolaamphiphiles through the sequential esterification of an alkyldioic acid, bearing distinct terminal protecting groups, with propanylamine and lyso-phosphatidylcholine headgroups. Bolaamphiphile self-assembly was investigated in solvent mixes of varying polarity by nuclear magnetic resonance (NMR) and Fourier transform-infrared (FT-IR) spectroscopy, as well as in water by cryo-high-resolution scanning electron microscopy (cryo-HRSEM). We anticipate that asymmetric lipid bolaamphiphiles will provide facile building blocks for engineering a variety of unique membrane-mimetic structures.