methyl 6-hydroxydodecanoate | 84770-43-4

• 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 6-hydroxydodecanoate
• 英文别名: Methyl 6-hydroxylaurate
• CAS: 84770-43-4
• 化学式: C₁₃H₂₆O₃
• 分子量: 230.348
• InChiKey: FDJOAIDQBSEUKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 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 6-hydroxydodecanoate 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 6-(4-vinylphenoxy)dodecanoic 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：

  6-羟基己酸甲酯 在 aluminum oxide 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 methyl 6-hydroxydodecanoate
  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

• CYP505E3: A Novel Self‐Sufficient ω‐7 In‐Chain Hydroxylase
  作者：Mpeyake Jacob Maseme、Alizé Pennec、Jacqueline Marwijk、Diederik Johannes Opperman、Martha Sophia Smit

  DOI：10.1002/anie.202001055

  日期：2020.6.22

  The self‐sufficient cytochrome P450 monooxygenase CYP505E3 from Aspergillus terreus catalyzes the regioselective in‐chain hydroxylation of alkanes, fatty alcohols, and fatty acids at the ω‐7 position. It is the first reported P450 to give regioselective in‐chain ω‐7 hydroxylation of C10–C16 n ‐alkanes, thereby enabling the one step biocatalytic synthesis of rare alcohols such as 5‐dodecanol and 7‐tetradecanol

  来自土曲霉的自给自足的细胞色素P450单加氧酶CYP505E3催化ω-7位烷烃，脂肪醇和脂肪酸的区域选择性链内羟化反应。这是第一个报道的P450，具有C10–C16 n的区域选择性链内ω-7羟基化作用链烷烃，从而一步一步生物催化合成稀有醇（如5-十二烷醇和7-十四烷醇）。它显示出一个甲基末端对第八个碳原子的区域选择性超过70％，并且对癸烷（TTN≈8000）和十二烷（TTN≈2000）的活性很高。CYP505E3可用于通过两种途径合成高价值风味化合物δ-十二内酯：1）将十二烷酸转化为5-羟基十二烷酸（区域选择性为24％），在低pH内酰胺酶下可转化为δ-十二内酯，以及2）转化将1-十二烷醇转化为1,5-十二烷二醇（55％的区域选择性），可以通过马肝醇脱氢酶将其转化为δ-十二烷内酯。
• 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.