ethyl 3-acetyloxy-4,4,4-trifluorobutanoate | 111860-17-4

• 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: ethyl 3-acetyloxy-4,4,4-trifluorobutanoate
• 英文别名: Butanoic acid, 3-(acetyloxy)-4,4,4-trifluoro-, ethyl ester
• CAS: 111860-17-4
• 化学式: C₈H₁₁F₃O₄
• 分子量: 228.168
• InChiKey: FCJBGMJILCJZGF-UHFFFAOYSA-N

物化性质

• 沸点：
  138.9±40.0 °C(Predicted)
• 密度：
  1.237±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 3-acetyloxy-4,4,4-trifluorobutanoate 在 disodium hydrogenphosphate 、 potassium dihydrogenphosphate 、 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 11.5h， 生成 ethyl (3S)-4,4,4-trifluoro-3-(oxan-2-yloxy)butanoate
  参考文献：
  名称：

  Synthetic approach to optically pure trifluoromethylated compounds

  摘要：

  DOI：

  10.1016/s0022-1139(00)85187-8

文献信息

• Method for making
  申请人：Rohm and Haas Company

  公开号：US05679832A1

  公开（公告）日：1997-10-21

  Disclosed are one and two step methods for preparing .alpha.,.beta.-unsaturated-.beta.-trifluoromethyl carboxylates and related materials under mild reaction conditions.

  披露了制备α，β-不饱和-β-三氟甲基羧酸酯及相关材料的一步和两步方法，在温和的反应条件下进行。
• Process for producing 4,4,4,- trifluoro-3-hydroxybutyric acid
  申请人：CENTRAL GLASS COMPANY, LIMITED

  公开号：US20030088095A1

  公开（公告）日：2003-05-08

  A first process for producing an optically active perfluoroalkylcarbinol derivative includes (a) reacting an optically active imine with a compound that is a hemiacetal of a perfluoroalkylaldehyde or a hydrate of a perfluoroalkylaldehyde to obtain a condensate; and (b) hydrolyzing the condensate under an acid condition. A second process for increasing optical purity of an optically active 4,4,4-trifluoro 3-hydroxy-1-aryl-1-butanone derivative includes (a) precipitating a racemic crystal of the derivative, from the derivative; and (b) removing the racemic crystal from the derivative. A third process for increasing optical purity of the butanone derivative includes recrystallizing the derivative. Novel compounds are optically active and inactive 4,4,4-trifluoro-3-hydroxybutanoic aryl ester derivatives. A fourth process for producing an optically active or optically inactive 4,4,4-trifluoro-3-hydroxybutyric acid aryl ester derivative includes oxidizing an optically active or optically inactive 4,4,4-trifluoro-3-hydroxy-1-aryl-1-butanone derivative. A fifth process for increasing optical purity of the optically active aryl ester derivative includes recrystallizing the derivative. A sixth process for producing an optically active 4,4,4-trifluoro-1,3-butanediol includes reducing the optically active aryl ester derivative by a hydride. A seventh process for producing an optically active or inactive 4,4,4-trifluoro-3-hydroxybutyric acid alkyl ester derivative includes reacting under an acid condition the optically active or optically inactive aryl ester derivative with a lower alcohol. It is possible to suitably combine at least two of the first to seventh processes.

  生产光学活性全氟烷基羟基甲基醇衍生物的第一种方法包括（a）将光学活性亚胺与半乙醇的全氟烷基醛或全氟烷基醛的水合物反应，以获得缩合物; （b）在酸性条件下水解缩合物。增加光学纯度的光学活性4,4,4-三氟-3-羟基-1-芳基-1-丁酮衍生物的第二种方法包括（a）从该衍生物中沉淀出外消旋晶体; （b）将外消旋晶体从衍生物中去除。增加丁酮衍生物光学纯度的第三种方法包括重结晶该衍生物。新化合物是光学活性和非活性的4,4,4-三氟-3-羟基丁酸芳基酯衍生物。生产光学活性或非活性的4,4,4-三氟-3-羟基丁酸芳基酯衍生物的第四种方法包括将光学活性或非活性的4,4,4-三氟-3-羟基-1-芳基-1-丁酮衍生物氧化。增加光学活性芳基酯衍生物光学纯度的第五种方法包括重结晶该衍生物。生产光学活性4,4,4-三氟-1,3-丁二醇的第六种方法包括通过氢化还原光学活性芳基酯衍生物。生产光学活性或非活性的4,4,4-三氟-3-羟基丁酸烷基酯衍生物的第七种方法包括在酸性条件下将光学活性或非活性的芳基酯衍生物与低级醇反应。可以适当地组合第一至第七种方法中的至少两种方法。
• Synthesis of optically active fluorinated materials by use of immobilized enzymes for asymmetric hydrolysis
  作者：Tomoya Kitazume、Naoko Okamura、Takanobu Ikeya、Takashi Yamazaki

  DOI：10.1016/s0022-1139(00)82741-4

  日期：1988.4

  A synthetic approach to optically active fluorinated compounds was based on the enantiotopic specificity of asymmetric hydrolysis by an immobilized enzyme.

  光学活性氟化化合物的合成方法基于固定化酶不对称水解的对映体特异性。
• Process for producing 4,4,4-trifluoro-3-hydroxybutyric acid derivatives
  申请人：——

  公开号：US20020016511A1

  公开（公告）日：2002-02-07

  A first process for producing an optically active perfluoroalkylcarbinol derivative includes (a) reacting an optically active imine with a compound that is a hemiacetal of a perfluoroalkylaldehyde or a hydrate of a perfluoroalkylaldehyde to obtain a condensate; and (b) hydrolyzing the condensate under an acid condition. A second process for increasing optical purity of an optically active 4,4,4-trifluoro-3-hydroxy-1-aryl-1-butanone derivative includes (a) precipitating a racemic crystal of the derivative, from the derivative; and (b) removing the racemic crystal from the derivative. A third process for increasing optical purity of the butanone derivative includes recrystallizing the derivative. Novel compounds are optically active and inactive 4,4,4-trifluoro-3-hydroxybutanoic aryl ester derivatives. A fourth process for producing an optically active or optically inactive 4,4,4-trifluoro-3-hydroxybutyric acid aryl ester derivative includes oxidizing an optically active or optically inactive 4,4,4-trifluoro-3-hydroxy-1-aryl-1-butanone derivative. A fifth process for increasing optical purity of the optically active aryl ester derivative includes recrystallizing the derivative. A sixth process for producing an optically active 4,4,4-trifluoro-1,3-butanediol includes reducing the optically active aryl ester derivative by a hydride. A seventh process for producing an optically active or inactive 4,4,4-trifluoro-3-hydroxybutyric acid alkyl ester derivative includes reacting under an acid condition the optically active or optically inactive aryl ester derivative with a lower alcohol. It is possible to suitably combine at least two of the first to seventh processes.

  生产光学活性全氟烷基醇衍生物的第一种方法包括：(a)将光学活性亚胺与半缩醛全氟烷基醛的半缩醛化合物或全氟烷基醛的水合物反应，获得缩合物；(b)在酸性条件下水解缩合物。第二种提高光学活性4,4,4-三氟-3-羟基-1-芳基-1-丁酮衍生物光学纯度的方法包括：(a)从该衍生物中沉淀出一个外消旋晶体；(b)将外消旋晶体从该衍生物中移除。第三种提高丁酮衍生物光学纯度的方法包括重结晶该衍生物。新化合物包括光学活性和非活性的4,4,4-三氟-3-羟基丁酸芳基酯衍生物。第四种生产光学活性或非活性4,4,4-三氟-3-羟基丁酸芳基酯衍生物的方法包括氧化光学活性或非活性的4,4,4-三氟-3-羟基-1-芳基-1-丁酮衍生物。第五种提高光学活性芳基酯衍生物光学纯度的方法包括重结晶该衍生物。第六种生产光学活性4,4,4-三氟-1,3-丁二醇的方法包括通过氢化还原光学活性芳基酯衍生物。第七种生产光学活性或非活性4,4,4-三氟-3-羟基丁酸烷基酯衍生物的方法包括在酸性条件下将光学活性或非活性芳基酯衍生物与低级醇反应。可以适当地结合第一到第七种方法中的至少两种方法。
• A method for making alpha, beta-unsaturated-beta-trifluoromethyl-carboxylates
  申请人：ROHM AND HAAS COMPANY

  公开号：EP0768296B1

  公开（公告）日：2001-06-13