1-(p-tolyl)tridecan-1-ol

• 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: 1-(p-tolyl)tridecan-1-ol
• 英文别名: 1-(4-Methylphenyl)tridecan-1-ol
• 化学式: C₂₀H₃₄O
• 分子量: 290.489
• InChiKey: MRBZVPSFPMISSB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  21
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(p-tolyl)tridecan-1-ol 在 Burkholderica cepacia amano lipase 作用下， 以 丙酮 为溶剂， 反应 0.5h， 生成 (R)-1-(p-methylphenyl)-1-tridecanol
  参考文献：
  名称：

  Synthesis of new (R)-secondary carbinols with different structures via enzymatic resolution

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2011.07.017
• 作为产物：
  描述：

  n-Dodecyl-(p-methylphenyl)-keton 在 sodium tetrahydroborate 作用下， 生成 1-(p-tolyl)tridecan-1-ol
  参考文献：
  名称：

  Asymmetric synthesis of new chiral 1,2- and 1,3-diols

  摘要：

  Seven chiral 1,2-diols and six chiral 1,3-diols were synthesized by the asymmetric reduction of the corresponding 1,2-diketones and 1,3-diketones using oxazaborolidine-BH3 catalyst. The 13 corresponding racemic 1,2- and 1,3-diols were synthesized by reducing the diketones with NaBH4 and they were used for determining the ee values through their chiral resolution on HPLC and GC. Five starting diketones, four racemic 1,2-diols, five chiral 1,2-diols, and two chiral 1,3-diols are novel compounds. The new chiral compounds were characterized by IR, H-1 and C-13 NMR, MS, and elemental analysis. The asymmetric reduction method, oxazaborolidine-BH3, was applied to these diketones for the first time in this study. The relationship between the structure of the diketone and the yield, diastereoselectivity, and enantiomeric excess was discussed.

  DOI：

  10.1007/s00706-012-0792-7

文献信息

• Rhodium-Catalysed Tandem Hydroformylation/Arylation Reaction with Boronic Acids
  作者：Ana R. Almeida、Roberto D. Dias、Carlos J. P. Monteiro、Artur R. Abreu、Pedro M. P. Gois、J. Carles Bayon、Mariette M. Pereira

  DOI：10.1002/adsc.201300968

  日期：2014.4.14

  A new efficient multicatalytic process involving a single catalyst to promote tandem hydroformylation/arylation reactions is disclosed. The effect of the rhodium ligand was evaluated and the rhodium/triphenylphosphine catalytic system was selected to apply the methodology to different olefins and boronic acids. High yields (up to 89%) and good to excellent isomer ratios (up to 98:2) were achieved using

  公开了一种涉及单个催化剂以促进串联加氢甲酰化/芳基化反应的新的有效多催化方法。评估了铑配体的作用，并选择了铑/三苯基膦催化体系，以将该方法应用于不同的烯烃和硼酸。使用芳基烯烃作为起始原料，可实现高收率（最高89％）和良好至出色的异构体比率（最高98：2）。这种新的方法可以从简单的烯烃制备仲醇，并为合成高价值产品（乙烯基吲哚和茴香脑衍生物）铺平了道路。
• Asymmetric synthesis of new chiral 1,2- and 1,3-diols
  作者：Tülay Yıldız、Ayşe Yusufoğlu

  DOI：10.1007/s00706-012-0792-7

  日期：2013.2

  Seven chiral 1,2-diols and six chiral 1,3-diols were synthesized by the asymmetric reduction of the corresponding 1,2-diketones and 1,3-diketones using oxazaborolidine-BH3 catalyst. The 13 corresponding racemic 1,2- and 1,3-diols were synthesized by reducing the diketones with NaBH4 and they were used for determining the ee values through their chiral resolution on HPLC and GC. Five starting diketones, four racemic 1,2-diols, five chiral 1,2-diols, and two chiral 1,3-diols are novel compounds. The new chiral compounds were characterized by IR, H-1 and C-13 NMR, MS, and elemental analysis. The asymmetric reduction method, oxazaborolidine-BH3, was applied to these diketones for the first time in this study. The relationship between the structure of the diketone and the yield, diastereoselectivity, and enantiomeric excess was discussed.
• 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.