methyl 10-hydroxydocosanoate | 328935-16-6

• 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: methyl 10-hydroxydocosanoate
• 英文别名: Methyl 10-hydroxydocosanoate
• CAS: 328935-16-6
• 化学式: C₂₃H₄₆O₃
• 分子量: 370.616
• InChiKey: VSFHLWJZSFNTQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  26
• 可旋转键数：
  21
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 10-hydroxydocosanoate 在 sodium hydroxide 、 三丁基膦 、 1,1'-azodicarbonyl-dipiperidine 作用下， 以 甲醇 、 水 、 甲苯 为溶剂， 反应 29.5h， 生成 10-(4-vinylphenoxy)docosanoic acid
  参考文献：
  名称：

  A New Family of Polymerizable Lyotropic Liquid Crystals:  Control of Feature Size in Cross-Linked Inverted Hexagonal Assemblies via Monomer Structure

  摘要：

  An efficient and versatile synthesis of a series of polymerizable amphiphilic mesogens that affords control over tail length and position of the :polymerizable group is described. The synthesis employs a novel and facile method of preparing styrene ethers. The monomers are sadium salts of styrene ether-modified fatty acids that can be used to form cross-linkable inverted hexagonal (H-II) lyotropic liquid crystal (LLC) phases at ambient temperature with controllable nanometer-scale dimensions. Examination of a series of regioisomers with the same alkyl chain length but with the styrene: ether group at different locations along the chain revealed that the position of the styrene ether has a profound effect on the dimensions of the resulting HII phase at a fixed temperature and composition. Increasing overall monomer tail length also has a significant, although smaller, effect on the unit cell dimensions of the LLC phase. By controlling the structure of the LLC monomer in this manner, cross-linked HII phases with interchannel distances (ICD) ranging from 29 to 54 Angstrom can be obtained. Furthermore, changing the counterion from Na+ to tetraalkylammonium ions leads to further expansion of the H-II unit cell to a maximum ICD of 65 Angstrom, as well as to the production of a lamellar phase. Use of these monomers affords a new and unparalleled degree of control over phase structure and dimensions for the production of nanostructured organic materials.

  DOI：

  10.1021/ja002462i
• 作为产物：
  描述：

  10-羟基癸酸 在 aluminum oxide 、 硫酸 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 22.0h， 生成 methyl 10-hydroxydocosanoate
  参考文献：
  名称：

  A New Family of Polymerizable Lyotropic Liquid Crystals:  Control of Feature Size in Cross-Linked Inverted Hexagonal Assemblies via Monomer Structure

  摘要：

  An efficient and versatile synthesis of a series of polymerizable amphiphilic mesogens that affords control over tail length and position of the :polymerizable group is described. The synthesis employs a novel and facile method of preparing styrene ethers. The monomers are sadium salts of styrene ether-modified fatty acids that can be used to form cross-linkable inverted hexagonal (H-II) lyotropic liquid crystal (LLC) phases at ambient temperature with controllable nanometer-scale dimensions. Examination of a series of regioisomers with the same alkyl chain length but with the styrene: ether group at different locations along the chain revealed that the position of the styrene ether has a profound effect on the dimensions of the resulting HII phase at a fixed temperature and composition. Increasing overall monomer tail length also has a significant, although smaller, effect on the unit cell dimensions of the LLC phase. By controlling the structure of the LLC monomer in this manner, cross-linked HII phases with interchannel distances (ICD) ranging from 29 to 54 Angstrom can be obtained. Furthermore, changing the counterion from Na+ to tetraalkylammonium ions leads to further expansion of the H-II unit cell to a maximum ICD of 65 Angstrom, as well as to the production of a lamellar phase. Use of these monomers affords a new and unparalleled degree of control over phase structure and dimensions for the production of nanostructured organic materials.

  DOI：

  10.1021/ja002462i

文献信息

• A New Family of Polymerizable Lyotropic Liquid Crystals:  Control of Feature Size in Cross-Linked Inverted Hexagonal Assemblies via Monomer Structure
  作者：Mary A. Reppy、David H. Gray、Brad A. Pindzola、Juston L. Smithers、Douglas L. Gin

  DOI：10.1021/ja002462i

  日期：2001.1.1

  An efficient and versatile synthesis of a series of polymerizable amphiphilic mesogens that affords control over tail length and position of the :polymerizable group is described. The synthesis employs a novel and facile method of preparing styrene ethers. The monomers are sadium salts of styrene ether-modified fatty acids that can be used to form cross-linkable inverted hexagonal (H-II) lyotropic liquid crystal (LLC) phases at ambient temperature with controllable nanometer-scale dimensions. Examination of a series of regioisomers with the same alkyl chain length but with the styrene: ether group at different locations along the chain revealed that the position of the styrene ether has a profound effect on the dimensions of the resulting HII phase at a fixed temperature and composition. Increasing overall monomer tail length also has a significant, although smaller, effect on the unit cell dimensions of the LLC phase. By controlling the structure of the LLC monomer in this manner, cross-linked HII phases with interchannel distances (ICD) ranging from 29 to 54 Angstrom can be obtained. Furthermore, changing the counterion from Na+ to tetraalkylammonium ions leads to further expansion of the H-II unit cell to a maximum ICD of 65 Angstrom, as well as to the production of a lamellar phase. Use of these monomers affords a new and unparalleled degree of control over phase structure and dimensions for the production of nanostructured organic materials.