1-苯基十四烷-1-醇 | 106560-86-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 1-苯基十四烷-1-醇
• 英文名称: Tridecyl-phenyl-carbinol
• 英文别名: Phenyltridecylcarbinol；1-phenyltetradecan-1-ol
• CAS: 106560-86-5
• 化学式: C₂₀H₃₄O
• 分子量: 290.489
• InChiKey: AEVLTPGKSSZINH-UHFFFAOYSA-N

物化性质

• 熔点：
  52.8-53.8 °C
• 沸点：
  360.8±10.0 °C(Predicted)
• 密度：
  0.911±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  21
• 可旋转键数：
  13
• 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-苯基十四烷-1-醇 在 Burkholderica cepacia amano lipase 作用下， 以 丙酮 为溶剂， 反应 96.5h， 生成 (R)-1-phenyl-1-tetradecanol
  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：

  十三烷基苯基酮 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 1-苯基十四烷-1-醇
  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

文献信息

• Switchable β-alkylation of Secondary Alcohols with Primary Alcohols by a Well-Defined Cobalt Catalyst
  作者：Bedraj Pandey、Shi Xu、Keying Ding

  DOI：10.1021/acs.organomet.1c00147

  日期：2021.5.10

  β-alkylation of secondary alcohols with primary alcohols to selectively generate alcohols by a well-defined Co catalyst is presented. Remarkably, a low catalyst loading of 0.7 mol % can be employed for the reaction. More significantly, this study represents the first Co-catalyzed switchable alcohol/ketone synthesis by simply manipulating the reaction parameters. In addition, the transformation is environmentally

  提出了通过定义明确的Co催化剂将仲醇与伯醇进行β-烷基化以选择性地产生醇的方法。显着地，可以将0.7mol％的低催化剂负载用于反应。更重要的是，该研究通过简单地控制反应参数代表了第一个共催化的可转换的醇/酮合成。此外，这种转化是环境友好的，水是唯一的副产品。
• CuI/H2/NaOH-Catalyzed Cross-Coupling of Two Different Alcohols for Carbon-Carbon Bond Formation: “Borrowing Hydrogen”?
  作者：Takashi Miura、Osamu Kose、Feng Li、Sun Kai、Susumu Saito

  DOI：10.1002/chem.201101752

  日期：2011.9.26

  Not borrowed: A new method was developed for the cross‐coupling of two different alcohols (see scheme). This carbon–carbon bond formation was realized by using a small amount of CuBr (0.05–0.2 mol %) and NaOH (4–20 mol %) in the presence of H2 (1 atm), and provides an alternative procedure for longer‐chain alcohols. The catalytic cycle was different from those reported to date for the Guerbet reaction

  不借用：开发了一种新方法，用于两种不同醇的交叉偶联（请参阅方案）。这种碳-碳键的形成是通过在H 2（1 atm）存在下使用少量的CuBr（0.05-0.2 mol％）和NaOH（4-20 mol％）来实现的，并为更长的时间提供了另一种方法。链醇。催化循环不同于迄今为止报道的涉及“借入氢”的Guerbet反应的催化循环。
• JP5854345
  申请人：——

  公开号：——

  公开（公告）日：——
• Breusch; Oguzer, Chemische Berichte, 1954, vol. 87, p. 1225,1227, 1228
  作者：Breusch、Oguzer

  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.