1-(4-hydroxy-phenyl)-tetradecan-1-one | 2589-75-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-hydroxy-phenyl)-tetradecan-1-one
• 英文别名: 1-(4-Hydroxy-phenyl)-tetradecan-1-on；Phenol, 4-tetradecanoyl-；1-(4-hydroxyphenyl)tetradecan-1-one
• CAS: 2589-75-5
• 化学式: C₂₀H₃₂O₂
• 分子量: 304.473
• InChiKey: ODJVEVORUCLLIG-UHFFFAOYSA-N

物化性质

• 熔点：
  78-80 °C
• 沸点：
  445.4±18.0 °C(Predicted)
• 密度：
  0.959±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  22
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-hydroxy-phenyl)-tetradecan-1-one 在 hydrazine hydrate 、 草酸 、 4-十二烷基苯磺酸钠盐 、 potassium hydroxide 作用下， 以 水 、 二乙二醇 为溶剂， 20.0~200.0 ℃ 、670.61 Pa 条件下， 反应 7.0h， 生成 bis(2-hydroxy-5-n-tetradecylphenyl)methane
  参考文献：
  名称：

  系列双子烷基酚聚氧乙烯非离子表面活性剂的合成及其临界胶束浓度

  摘要：

  成功合成了一系列双子正烷基酚聚氧乙烯表面活性剂（GAP），并通过NMR和FTIR光谱确定了它们的分子结构。使用相同的合成路线，使用工业壬基酚产品和多聚甲醛合成了双基壬基酚聚氧乙烯表面活性剂（GNP），其分子结构也由1表征H-NMR和FTIR光谱。确定了最佳反应条件。通过Wilhelmy平板法和稳态荧光探针法测定GAP的临界胶束浓度（CMC）值。实验结果表明，亲水性聚氧乙烯链和疏水性尾部的长度如何改变CMC值。发现GAP的CMC值比聚乙氧基化烷基酚型的相应常规单尾非离子表面活性剂的CMC值低得多，这表明双子物种具有更好的表面活性。

  DOI：

  10.1007/s11743-011-1245-8
• 作为产物：
  描述：

  肉豆蔻酸苯酯 在 aluminum (III) chloride 作用下， 反应 3.5h， 生成 1-(4-hydroxy-phenyl)-tetradecan-1-one
  参考文献：
  名称：

  系列双子烷基酚聚氧乙烯非离子表面活性剂的合成及其临界胶束浓度

  摘要：

  成功合成了一系列双子正烷基酚聚氧乙烯表面活性剂（GAP），并通过NMR和FTIR光谱确定了它们的分子结构。使用相同的合成路线，使用工业壬基酚产品和多聚甲醛合成了双基壬基酚聚氧乙烯表面活性剂（GNP），其分子结构也由1表征H-NMR和FTIR光谱。确定了最佳反应条件。通过Wilhelmy平板法和稳态荧光探针法测定GAP的临界胶束浓度（CMC）值。实验结果表明，亲水性聚氧乙烯链和疏水性尾部的长度如何改变CMC值。发现GAP的CMC值比聚乙氧基化烷基酚型的相应常规单尾非离子表面活性剂的CMC值低得多，这表明双子物种具有更好的表面活性。

  DOI：

  10.1007/s11743-011-1245-8

文献信息

• Asymmetric synthesis of new chiral long chain alcohols
  作者：Tülay Yıldız、Ayşe Yusufoğlu

  DOI：10.1016/j.tetasy.2010.12.010

  日期：2010.12

  Sixteen new chiral alcohols with alkyl (C-11-C-19) and aryl, substituted aryl, hetero aryl and biaryl groups 2a-2t were synthesized by three different asymmetric reduction methods from their corresponding ketones 1a-1t. Chiral NaBH4 (method A), chiral BH3 (method B) and chiral AIP (method C) were used as asymmetric reduction catalysts. Chiral NaBH4 was modified by four different ligands 3a-3d, chiral BH3 and chiral AIP by four different ligands 4a-4d. Ligand 4c was synthesized for the first time in this work. Chiral NaBH4 generated chiral alcohols of (R)-configuration and chiral BH3 and chiral AIP of (S)-configuration with high enantiomeric excesses, were analysed by chiral HPLC. In order to determine the ee values by chiral HPLC, sixteen corresponding racemic alcohols, synthesized by reducing their corresponding ketones via NaBH4, were used for chiral resolution on a Daicel OD HPLC column. The sixteen starting ketones were synthesized in this study by Friedel-Craft acylation. The new chiral alcohols were characterized by IR, NMR, (H-1 and C-13), MS, elemental analyses and specific rotation. The reduction methods A, B and C were applied to these ketones for the first time in this study and were compared with each other. The relationship between the structure of the ketone and the yield and the enantiomeric excess was discussed. (C) 2010 Elsevier Ltd. All rights reserved.
• Heinrich, B.; Guillon, D., Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 1995, vol. 268, p. 21 - 44
  作者：Heinrich, B.、Guillon, D.

  DOI：——

  日期：——
• Synthesis of new (R)-secondary carbinols with different structures via enzymatic resolution
  作者：Tülay Yıldız、Ayşe Yusufoğlu

  DOI：10.1016/j.tetasy.2011.07.017

  日期：2011.6

  The present study deals with the biocatalytic enantioselective synthesis of 19 new chiral alcohols with alkyl (C-11-C-19) and phenyl, substituted phenyl, heteroaromatic, and naphthyl groups 4a-4z with an (R)-configuration and high enantiomeric excess (similar to 100%). The corresponding ketones 1a-1z were synthesized and then reduced with NaBH4 to their racemic alcohols 2a-2z, which were converted into their racemic acetyl derivatives 3a-3z. Enzymes of four different types were used for the enantioselective hydrolysis of these acetyl compounds 3a-3z. The optimal reaction conditions for these four enzymes were established by investigating the enantiomeric excesses by chiral HPLC. Amano lipase from Burkholderica cepacia (Pseudomonas cepacia) AL-PS was determined as the best enzyme in this work This study presents an environmentally friendly and green chemistry method for the synthesis of these new (R)-chiral carbinols 4a-4z. (C) 2011 Elsevier Ltd. All rights reserved.
• Corrosion Control of Subsea Production Control Systems: Twenty Years' Experience
  作者：Tomas Sydberger、Trude Helgesen

  DOI：10.1177/002029400003300706

  日期：2000.9
• Ralston; Bauer, Journal of Organic Chemistry, 1940, vol. 5, p. 169
  作者：Ralston、Bauer

  DOI：——

  日期：——