1-heneicosyl-3,5-dimethoxybenzene | 96377-24-1

• 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-heneicosyl-3,5-dimethoxybenzene
• 英文别名: 5-Heneicosyl-resorcin-dimethylether；1-henicosyl-3,5-dimethoxybenzene
• CAS: 96377-24-1
• 化学式: C₂₉H₅₂O₂
• 分子量: 432.731
• InChiKey: CGHRAXIZYRXFKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.68
• 重原子数：
  31.0
• 可旋转键数：
  22.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-heneicosyl-3,5-dimethoxybenzene 在 吡啶 、 吡啶盐酸盐 作用下， 生成 5-Heneicosyl-resorcin-diacetat
  参考文献：
  名称：

  Wheat Bran Phenols¹

  摘要：

  DOI：

  10.1021/jo01025a046
• 作为产物：
  描述：

  3,5-二甲氧基苄醇 在 dilithium tetrachlorocuprate 、 三溴化磷 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 生成 1-heneicosyl-3,5-dimethoxybenzene
  参考文献：
  名称：

  Properties of mixed monolayers and bilayers of long-chain 5-n-alkylresorcinols and dipalmitoylphosphatidylcholine

  摘要：

  5-n-Alkylresorcinols with different chain length are known to occur in different plants and procaryonts, for example in the cysts of the Azotobacter genus. To study the monolayer and bilayer behaviour of these amphiphilic compounds, we synthesized three analogues with different chain length, namely 5-n-octadecylresorcinol (18AR), 5-n-nonadecylresorcinol(19AR) and 5-n-heneicosylresorcinol (21AR). The pure alkylresorcinols form stable monolayers, 18AR and 19AR, show a phase transition from a liquid-condensed to a liquid-expanded state at temperatures between 20 and 40 degrees C and at lateral pressures below 15 dyn/cm. In mixtures with dipalmitoylphosphatidylcholine (DPPC), monolayer isobars at higher lateral pressures (20-30 dyn/cm) show an increase in the transition temperature to values greater than 50 degrees C for the liquid-condensed to liquid-expanded state of DPPC when the alkylresorcinol content is increased. Particularly in the liquid-expanded state, alkylresorcinols show a strong condensing effect on DPPC monolayers. 18AR/DPPC monolayers at a pressure of 5 dyn/cm show indications of an azeotropic behaviour. A similar increase in transition temperature is observed by differential scanning calorimetry (DSC) and differential scanning densitometry (DSD) in DPPC/alkylresorcinol bilayers. The transition enthalpy decreases with increasing alkylresorcinol content. All alkylresorcinols seem to be completely miscible with DPPC up to at least 50 mol%. The DSD data indicate a slight condensing effect of the alkylresorcinols on the liquid-crystalline phase of DPPC.

  DOI：

  10.1016/0009-3084(94)90074-4

文献信息

• An expedient synthesis of 5-<i>n</i>-alkylresorcinols and novel 5-<i>n</i>-alkylresorcinol haptens
  作者：Kirsti Parikka、Kristiina Wähälä

  DOI：10.3762/bjoc.5.22

  日期：——

  The first synthesis of bioactive long alkyl chain 5-n-alkylresorcinols, present in whole grain products, by a novel modification of the Wittig reaction is described. All the main long chain 5-n-alkylresorcinols present in rye and wheat, including C₂₃ and C₂₅ analogues and haptens, which have not been previously prepared, were synthesised. Microwave-promoted reactions of a semi-stabilized ylid and alkanals in water gave good yields in both pressurized and open systems. An alternative microwave-promoted synthesis starting from non-stabilized alkyltriphenylphosphonium salts and 3,5-dimethoxybenzaldehyde worked as well. Aqueous media were suitable for the reactions even if the starting materials were not soluble in water. The 5-n-alkylresorcinols are potential biomarkers of whole grain intake, and the new hapten derivatives of 5-n-alkylresorcinols will open the way for the immunochemical detection techniques of alkylresorcinols.

  描述了通过一种新颖的Wittig反应改进合成生物活性长烷基链5-烷基间苯二酚，这种物质存在于全谷物产品中。合成了黑麦和小麦中所有主要的长链5-烷基间苯二酚，包括C23和C25类似物以及以前未制备的半抗原。在水中，半稳定叶立德和烷醛的微波促进反应在加压和开放系统中均获得良好产率。另一种微波促进合成方法是从非稳定的烷基三苯基膦盐和3,5-二甲氧基苯甲醛出发。即使起始材料在水中不溶解，水介质也适用于这些反应。5-烷基间苯二酚是全谷物摄入的潜在生物标志物，而新的5-烷基间苯二酚半抗原衍生物将为烷基间苯二酚的免疫化学检测技术打开道路。
• Wheat Bran Phenols¹
  作者：Ernest Wenkert、Eva-Marie Loeser、Shiba N. Mahapatra、Fausto Schenker、Edward M. Wilson

  DOI：10.1021/jo01025a046

  日期：1964.2
• Properties of mixed monolayers and bilayers of long-chain 5-n-alkylresorcinols and dipalmitoylphosphatidylcholine
  作者：Sabine Gerdon、Stefan Hoffmann、Alfred Blume

  DOI：10.1016/0009-3084(94)90074-4

  日期：1994.5

  5-n-Alkylresorcinols with different chain length are known to occur in different plants and procaryonts, for example in the cysts of the Azotobacter genus. To study the monolayer and bilayer behaviour of these amphiphilic compounds, we synthesized three analogues with different chain length, namely 5-n-octadecylresorcinol (18AR), 5-n-nonadecylresorcinol(19AR) and 5-n-heneicosylresorcinol (21AR). The pure alkylresorcinols form stable monolayers, 18AR and 19AR, show a phase transition from a liquid-condensed to a liquid-expanded state at temperatures between 20 and 40 degrees C and at lateral pressures below 15 dyn/cm. In mixtures with dipalmitoylphosphatidylcholine (DPPC), monolayer isobars at higher lateral pressures (20-30 dyn/cm) show an increase in the transition temperature to values greater than 50 degrees C for the liquid-condensed to liquid-expanded state of DPPC when the alkylresorcinol content is increased. Particularly in the liquid-expanded state, alkylresorcinols show a strong condensing effect on DPPC monolayers. 18AR/DPPC monolayers at a pressure of 5 dyn/cm show indications of an azeotropic behaviour. A similar increase in transition temperature is observed by differential scanning calorimetry (DSC) and differential scanning densitometry (DSD) in DPPC/alkylresorcinol bilayers. The transition enthalpy decreases with increasing alkylresorcinol content. All alkylresorcinols seem to be completely miscible with DPPC up to at least 50 mol%. The DSD data indicate a slight condensing effect of the alkylresorcinols on the liquid-crystalline phase of DPPC.