(S)-1,1,1-trifluorodecan-2-yl acetate | 175776-99-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-1,1,1-trifluorodecan-2-yl acetate
• 英文别名: [(2S)-1,1,1-trifluorodecan-2-yl] acetate
• CAS: 175776-99-5
• 化学式: C₁₂H₂₁F₃O₂
• 分子量: 254.293
• InChiKey: DLPHKBNNECDRMM-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  17
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 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)-1,1,1-trifluorodecan-2-yl acetate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 (S)-(-)-1,1,1-三氟-2-癸醇
  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
• 作为产物：
  描述：

  正辛基镁溴盐 在 sodium tetrahydroborate 、 lipase CAL 作用下， 以 甲醇 、 正己烷 为溶剂， 反应 280.0h， 生成 (S)-1,1,1-trifluorodecan-2-yl acetate
  参考文献：
  名称：

  Efficient Synthesis of Optically Pure 1,1,1-Trifluoro-2-alkanols through Lipase-Catalyzed Acylation in Organic Media

  摘要：

  Lipase-catalyzed esterification was successfully utilized for the optical resolution of 1,1,1-trifluoro-2-alkanol 1 when racemic 1 was treated with lipase from Candida antarctica in hexane in the presence of molecular sieves (4 Angstrom) to provide the corresponding (S)-acetate 2 in an optically pure state. Alkanol 1 is known as an important component of liquid crystal compounds which display remarkable ferroelectric liquid crystal (FLC) characteristics. Five types of optically pure alkanols, i.e., 1,1,1-trifluoro-2-octanol (1a), 1,1,1-trifluoro-2-nonanol (1b), 1,1,1-trifluoro-2-decanol (1c), 1,1,1-trifluoro-2-undecanol (1d), and 1,1,1-trifluoro-8-(benzyloxy)-2-octanol (1e), were thus obtained by the lipase-catalyzed acylation.

  DOI：

  10.1021/jo951976a

文献信息

• Enantioselective synthesis of 1,1,1-trifluoroalkan-2-ols by ruthenium-catalyzed hydrogenation
  作者：Yoshichika Kuroki、Daisuke Asada、Yuko Sakamaki、Katsuhiko Iseki

  DOI：10.1016/s0040-4039(00)00643-2

  日期：2000.6

  The highly enantioselective synthesis of 1,1,1-trifluoroalkan-2-ols has been achieved by hydrogenating 1,1,1-trifluoroalkan-2-one enol acetates in the presence of chiral ruthenium catalysts. An enol acetate, 2-acetoxy-3,3,3-trifluoro-1-(phenylthio)propene, can be successfully transformed into enantiomerically pure trifluorolactic acid.

  在手性钌催化剂的存在下，通过氢化1,1,1-三氟烷-2-酮烯醇乙酸酯可以实现1,1,1-三氟烷-2-酮烯醇的高度对映选择性合成。烯醇乙酸酯2-乙酰氧基-3,3,3-三氟-1-（苯硫基）丙烯可成功转化为对映体纯的三氟乳酸。
• LIN, JENG TAIN;YAMAZAKI, TAKASHI;KITAZUME, TOMOYA, J. ORG. CHEM., 52,(1987) N 15, 3211-3217
  作者：LIN, JENG TAIN、YAMAZAKI, TAKASHI、KITAZUME, TOMOYA

  DOI：——

  日期：——