(S)-α-naphthyl trifluoromethyl carbinol acetate | 158849-50-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-α-naphthyl trifluoromethyl carbinol acetate
• 英文别名: [(1S)-2,2,2-trifluoro-1-naphthalen-1-ylethyl] acetate
• CAS: 158849-50-4
• 化学式: C₁₄H₁₁F₃O₂
• 分子量: 268.235
• InChiKey: WTGOWJFUHRFCLV-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-α-naphthyl trifluoromethyl carbinol acetate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 -α-(Trifluormethyl)-1-naphtalinmethanol
  参考文献：
  名称：

  Lipase-catalysed enantioselective synthesis of naphthyl trifluoromethyl carbinols and their corresponding non-fluorinated counterparts

  摘要：

  Enantioselective synthesis of both enantiomers of beta- and alpha-naphthyl trifluoromethyl carbinols (R)1a, (s)-1a, (R)-2a, (S)-2a has been achieved through acylation of the corresponding racemic alcohols (RS)-1a and (RS)-2a with vinyl acetate in the presence-of lipase PS. The effect of fluorine atoms on the extent and enantioselectivity of the process has been tested by carrying out the same biocatalytic transformation on their non-fluorinated counterparts (RS)-1b and (RS)-2b. The order of reactivity follows the trend (RS)-1b > (RS)2b approximate to (RS)-1a > (RS)-2a. Effect of the hydrophobicity of the solvent in the resolution of (RS)-1a is also presented.

  DOI：

  10.1016/0957-4166(94)00379-p
• 作为产物：
  描述：

  乙酸乙烯酯 、 2,2,2-trifluoro-1-(1-naphthyl)ethanol 以 正己烷 为溶剂， 反应 25.0h， 生成 (S)-α-naphthyl trifluoromethyl carbinol acetate
  参考文献：
  名称：

  Lipase-catalysed enantioselective synthesis of naphthyl trifluoromethyl carbinols and their corresponding non-fluorinated counterparts

  摘要：

  Enantioselective synthesis of both enantiomers of beta- and alpha-naphthyl trifluoromethyl carbinols (R)1a, (s)-1a, (R)-2a, (S)-2a has been achieved through acylation of the corresponding racemic alcohols (RS)-1a and (RS)-2a with vinyl acetate in the presence-of lipase PS. The effect of fluorine atoms on the extent and enantioselectivity of the process has been tested by carrying out the same biocatalytic transformation on their non-fluorinated counterparts (RS)-1b and (RS)-2b. The order of reactivity follows the trend (RS)-1b > (RS)2b approximate to (RS)-1a > (RS)-2a. Effect of the hydrophobicity of the solvent in the resolution of (RS)-1a is also presented.

  DOI：

  10.1016/0957-4166(94)00379-p

文献信息

• Preparation and Lipase-catalyzed Optical Resolution of 2,2,2-Trifluoro-1-(naphthyl) ethanols
  作者：Katsuya Kato、Masato Katayama、Rakesh K. Gautam、Shozo Fujii、Hiroshi Kimoto

  DOI：10.1271/bbb.59.271

  日期：1995.1

  The optical resolution of racemic 2,2,2-trifluoro-1-(naphthyl)ethanols (TFNEs) was achieved by lipase-catalyzed enantioselective acetylation with vinyl acetate in octane, S-acetates and R-alcohols being obtained. The introduction of a methyl group into the naphthalene ring at the 4-position (2b) or the 2-position (2c) markedly decreased the reactivity, in particular for 2c. 2,2,2-Trifluoro-1-(1-naphthyl)ethanol (2a) behaved differently from the regio-isomer, 2,2,2-trifluoro-1-(2-naphthyl)ethanol (2d): The enantioselectivity of lipases [LIP (Pseudomonas), PLC (Alcaligenes), and ALC (Achromobacter)] was high for 2a but low for 2d, whereas lipases [AK and PS (Pseudomonas)] exhibited higher selectivity for 2d than for 2a. Three other derivatives, 2,2,2-trifluoro-1-(phenyl)ethanol (2e), 2,2,2-trifluoro-1-(indol-3-yl)ethanol (2f), and 1-(1-naphthyl)ethanol (2g), were prepared, and their behaviors with respect to lipase-catalyzed acetylation were compared with 2a.

  对消旋体2,2,2-三氟-1-(萘基)乙醇（TFNEs）的光学分辨率是通过在正庚烷中用脂肪酶催化的对映选择性醋酸化实现的，得到S-醋酸酯和R-醇。将甲基引入萘环的4位（2b）或2位（2c）显著降低了反应活性，特别是对于2c。2,2,2-三氟-1-(1-萘基)乙醇（2a）与其区域异构体2,2,2-三氟-1-(2-萘基)乙醇（2d）表现出不同的行为：脂肪酶[LIP（假单胞菌）、PLC（阿尔卡利菌）和ALC（嗜色菌）]对2a的对映选择性较高，但对2d较低，而脂肪酶[AK和PS（假单胞菌）]对2d的选择性高于对2a。还合成了另外三个衍生物，2,2,2-三氟-1-(苯基)乙醇（2e）、2,2,2-三氟-1-(吲哚-3-基)乙醇（2f）和1-(1-萘基)乙醇（2g），并将它们在脂肪酶催化的醋酸化中的表现与2a进行了比较。
• Kato, Katsuya; Katayama, Masato; Gautam, Rakesh K., Bioscience, Biotechnology and Biochemistry, 1994, vol. 58, # 7, p. 1353 - 1354
  作者：Kato, Katsuya、Katayama, Masato、Gautam, Rakesh K.、Fujii, Shozo、Kimoto, Hiroshi

  DOI：——

  日期：——