(S)-2-tetradecanol | 82272-45-5

• 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: (S)-2-tetradecanol
• 英文别名: 2-tetradecanol；(2S)-Tetradecan-2-OL
• CAS: 82272-45-5
• 化学式: C₁₄H₃₀O
• 分子量: 214.392
• InChiKey: BRGJIIMZXMWMCC-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  15
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  (S)-2-tetradecanol 、 N-(2,6-diisopropyl-phenyl)-malonamic acid 在 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 N-(2,6-Diisopropyl-phenyl)-malonamic acid (S)-1-methyl-tridecyl ester
  参考文献：
  名称：

  Inhibitors of acyl-CoA: cholesterol O-acyl transferase (ACAT) as hypocholesterolemic agents. The synthesis and biological activity of a series of malonester amides

  摘要：

  The synthesis and structure-activity relationships of a series of malonester amide ACAT inhibitors are described. One of these compounds, 4s, was shown to be a potent inhibitor of both the intestinal and arterial enzymes, bioactive upon oral dosing (ex vivo bioassay) and efficacious in a clinically relevant rodent model of preestablished hypercholesterolemia.

  DOI：

  10.1016/0960-894x(96)00098-4
• 作为产物：
  描述：

  2-十四醇 生成 (S)-2-tetradecanol
  参考文献：
  名称：

  Highly enantioselective synthesis of long chain alkyl trifluoromethyl carbinols and β-thiotrifluoromethyl carbinols through lipases

  摘要：

  Among a variety of lipases tested, Candida antarctica lipase has been found to promote the enantioselective acylation of long chain alkyl trifluoromethyl carbinols 1a-4a and beta-thiotrifluoromethyl carbinols 5a-7a, producing both R and S enantiomeric alcohols in good to excellent chemical yield and enantioselectivity. In all cases the lipase preferentially acylates the S enantiomer, irrespective the presence or not of a sulfur atom in beta position to the hydroxyl group, When the reaction was carried out on the non-fluorinated substrates 1c-2c, the process occurred much faster and with higher e.e. of the less reacting enantiomer than when conducted on the fluorinated substrates. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00256-x

文献信息

• Enantioselective helical folding inside a self-assembled, cylindrical capsule
  作者：Carsten Siering、Jakob Toräng、Holger Kruse、Stefan Grimme、Siegfried R. Waldvogel

  DOI：10.1039/b925334c

  日期：——

  The combination of experimental with theoretical CD spectroscopy allows the observation of stereoselective helical folding in a self-assembled capsule.

  实验与理论CD光谱学的结合，使得人们能够观察到自组装胶囊中的立体
• Asymmetric enzymatic hydration of unactivated terminal alkenes by two promiscuous oleate hydratases mined from marine metagenome
  作者：Ya-Ru Zhao、Jing-Qi Zhang、Yu-Cai He、Xuan Deng、Hang Gao、Juan Zhang、Shuang-Ping Huang、Li-Li Gao、Jian-Dong Zhang

  DOI：10.1016/j.mcat.2023.113249

  日期：2023.7

  Enantiopure alcohols are very important chemicals as highly valuable building blocks in the synthesis of pharmaceuticals, agrochemicals and materials. The direct enantioselective hydration of unactivated 1-alkenes is a highly straightforward and atom economy approach to access chiral alcohols, though quite challenging in organic synthesis owing to low selectivity and many environmental concerns. Herein

  对映体纯醇是非常重要的化学品，是药物、农用化学品和材料合成中非常有价值的结构单元。未活化的 1-烯烃的直接对映选择性水合是一种非常简单且原子经济的获得手性醇的方法，但由于选择性低和许多环境问题，在有机合成中相当具有挑战性。在此，通过基于序列的挖掘方法从海洋宏基因组中鉴定出两种新型油酸水合酶（MmOAH1和MmOAH2），并且这两种OAH在T7中进行功能表达、纯化和表征。当羧酸诱饵分子参与反应时，这两种 OAH 都对未活化的 1-烯烃表现出令人惊讶的高度混杂的水合酶活性。除了其天然底物油酸外，通过使用 (MmOAH1) 和 (MmOAH2) 的静息细胞，一系列未活化的 1-烯烃被转化为 ()-醇，转化率中等至良好 (6–90%) 和优秀 (>98) ％）获得。还用 1-癸烯和 1-十三烯进行了制备规模实验，以良好的收率和优异的 (>99%) 提供 ()-2-癸醇和 ()-2-十三醇。这项研究
• Inhibitors of acyl-CoA: cholesterol O-acyl transferase (ACAT) as hypocholesterolemic agents. The synthesis and biological activity of a series of malonester amides
  作者：D.R. Sliskovic、J.A. Picard、W.H. Roark、A.D. Essenburg、B.R. Krause、L.L. Minton、J.F. Reindel、R.L. Stanfield

  DOI：10.1016/0960-894x(96)00098-4

  日期：1996.3

  The synthesis and structure-activity relationships of a series of malonester amide ACAT inhibitors are described. One of these compounds, 4s, was shown to be a potent inhibitor of both the intestinal and arterial enzymes, bioactive upon oral dosing (ex vivo bioassay) and efficacious in a clinically relevant rodent model of preestablished hypercholesterolemia.
• Highly enantioselective synthesis of long chain alkyl trifluoromethyl carbinols and β-thiotrifluoromethyl carbinols through lipases
  作者：Inés Petschen、Edi A. Malo、M.P. Bosch、Angel Guerrero

  DOI：10.1016/0957-4166(96)00256-x

  日期：1996.7

  Among a variety of lipases tested, Candida antarctica lipase has been found to promote the enantioselective acylation of long chain alkyl trifluoromethyl carbinols 1a-4a and beta-thiotrifluoromethyl carbinols 5a-7a, producing both R and S enantiomeric alcohols in good to excellent chemical yield and enantioselectivity. In all cases the lipase preferentially acylates the S enantiomer, irrespective the presence or not of a sulfur atom in beta position to the hydroxyl group, When the reaction was carried out on the non-fluorinated substrates 1c-2c, the process occurred much faster and with higher e.e. of the less reacting enantiomer than when conducted on the fluorinated substrates. Copyright (C) 1996 Elsevier Science Ltd