methyl 2-(acetylthio)-3-phenylpropanoate | 255869-04-6

• 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: methyl 2-(acetylthio)-3-phenylpropanoate
• 英文别名: methyl 2-acetylthio-3-phenylpropionate；methyl 2-acetylsulfanyl-3-phenylpropanoate
• CAS: 255869-04-6
• 化学式: C₁₂H₁₄O₃S
• 分子量: 238.307
• InChiKey: OZBNLZSEFKEFQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  68.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  硫代乙酸 、 肉桂酸甲酯 在 苯并咪唑并[2,1-A]苯并[D,E]异奎千酮-7-酮 作用下， 以 环己烷 为溶剂， 反应 1.0h， 以77%的产率得到methyl 2-(acetylthio)-3-phenylpropanoate
  参考文献：
  名称：

  质子耦合电子转移引发的可见光介导的有机催化硫醇-烯反应

  摘要：

  描述了一种进行硫醇-烯反应的简便方法。该反应在蓝光照射下进行，并由光活性的路易斯碱性分子如a啶橙或萘稠合的N-酰基苯并咪唑催化。据信该过程是由硫醇和路易斯碱性催化剂之间的配合物中的质子偶联电子转移过程引发的。

  DOI：

  10.1021/acs.joc.9b01331

文献信息

• Process for producing optically active carboxylic acid subtituted in 2-position
  申请人：——

  公开号：US20030144546A1

  公开（公告）日：2003-07-31

  A nitrous acid salt is added at a temperature of 10 to 80° C. to an aqueous solution which contains an optically active 2-aminocarboxylic acid (4) and a protonic acid, the amount of the latter acid being 1 to 3 equivalents to the former, and which has a proton concentration of 0.5 to 2 mol/kg to conduct a reaction to thereby produce an optically active 2-hydroxycarboxylic acid (1). Thionyl chloride and a basic compound are caused to act on the compound (1) to chlorinate it and simultaneously invert the configuration in the 2-position. Thus, an optically active 2-chlorocarboxylic acid chloride (5) is induced. The compound (5) is hydrolyzed to induce an optically active 2-chlorocarboxylic acid (2). The compound (2) is reacted with a thioacetic acid salt to incorporate an acetylthio group thereinto and simultaneously invert the configuration in the 2-position to thereby produce an optically active 2-acetylthiocarboxylic acid (3). 1

  在温度为10至80°C的水溶液中，加入一种亚硝酸盐，该水溶液含有一个光学活性的2-氨基羧酸（4）和一个质子酸，后者的量为前者的1至3当量，并且具有0.5至2mol/kg的质子浓度，以进行反应从而产生一个光学活性的2-羟基羧酸（1）。然后，使亚硫酰氯和一种碱性化合物作用于化合物（1）以进行氯化，并同时颠倒2位构型。因此，诱导出一个光学活性的2-氯羧酸氯化物（5）。化合物（5）经水解产生一个光学活性的2-氯羧酸（2）。将化合物（2）与硫乙酸盐反应以在其中引入一个乙酰硫基团，并同时颠倒2位构型，从而产生一个光学活性的2-乙酰硫基羧酸（3）。
• Process for crystallization of 2-acetylthio-3-phenyl-propionic acid
  申请人：——

  公开号：US20030013903A1

  公开（公告）日：2003-01-16

  The present invention provides an industrial method for recovering and purifying 2-acetylthio-3-phenylpropionic acid, particularly an optically active 2-acetylthio-3-phenylpropionic acid, as crystals of the free acid. 2-Acetylthio-3-phenylpropionic acid is recovered and purified as crystals of the free acid by using an aliphatic hydrocarbon solvent and/or an aromatic hydrocarbon solvent.

  本发明提供了一种工业方法，用于回收和纯化2-乙酰硫基-3-苯基丙酸，特别是光学活性的2-乙酰硫基-3-苯基丙酸，以自由酸的晶体形式。使用脂肪烃溶剂和/或芳香烃溶剂将2-乙酰硫基-3-苯基丙酸作为自由酸的晶体回收和纯化。
• Process for producing optically active carboxylic acid substituted in 2-position
  申请人：Amano Susumu

  公开号：US20060247470A1

  公开（公告）日：2006-11-02

  A nitrous acid salt is added at a temperature of 10 to 80° C. to an aqueous solution which contains an optically active 2-aminocarboxylic acid (4) and a protonic acid, the amount of the latter acid being 1 to 3 equivalents to the former, and which has a proton concentration of 0.5 to 2 mol/kg to conduct a reaction to thereby produce an optically active 2-hydroxycarboxylic acid (1). Thionyl chloride and a basic compound are caused to act on the compound (1) to chlorinate it and simultaneously invert the configuration in the 2-position. Thus, an optically active 2-chlorocarboxylic acid chloride (5) is induced. The compound (5) is hydrolyzed to induce an optically active 2-chlorocarboxylic acid (2). The compound (2) is reacted with a thioacetic acid salt to incorporate an acetylthio group thereinto and simultaneously invert the configuration in the 2-position to thereby produce an optically active 2-acetylthiocarboxylic acid (3).

  在含有手性的2-氨基羧酸（4）和质子酸的水溶液中，将一种亚硝酸盐在10至80°C的温度下加入，其中后者的数量是前者的1到3当量，质子浓度为0.5至2mol/kg，以进行反应，从而产生手性的2-羟基羧酸（1）。然后，将亚磺酰氯和碱性化合物作用于化合物（1）以氯化它并同时反转2位的构型。因此，引入了手性的2-氯羧酸氯化物（5）。将化合物（5）水解以引入手性的2-氯羧酸（2）。将化合物（2）与一种硫代乙酸盐反应，将乙酰硫基并入其中并同时反转2位的构型，从而产生手性的2-乙酰硫基羧酸（3）。
• PROCESS FOR PRODUCING OPTICALLY ACTIVE CARBOXYLIC ACID SUBSTITUTED IN 2-POSITION
  申请人：KANEKA CORPORATION

  公开号：EP1251115A1

  公开（公告）日：2002-10-23

  A nitrous acid salt is added at a temperature of 10 to 80°C to an aqueous solution which contains an optically active 2-aminocarboxylic acid (4) and a protonic acid, the amount of the latter acid being 1 to 3 equivalents to the former, and which has a proton concentration of 0.5 to 2 mol/kg to conduct a reaction to thereby produce an optically active 2-hydroxycarboxylic acid (1). Thionyl chloride and a basic compound are caused to act on the compound (1) to chlorinate it and simultaneously invert the configuration in the 2-position. Thus, an optically active 2-chlorocarboxylic acid chloride (5) is induced. The compound (5) is hydrolyzed to induce an optically active 2-chlorocarboxylic acid (2). The compound (2) is reacted with a thioacetic acid salt to incorporate an acetylthio group thereinto and simultaneously invert the configuration in the 2-position to thereby produce an optically active 2-acetylthiocarboxylic acid (3).

  在 10 至 80°C 的温度下，向含有光学活性 2-氨基羧酸 (4) 和质子酸的水溶液中加入亚硝酸盐，后者的量为前者的 1 至 3 个当量，质子浓度为 0.5 至 2 摩尔/千克，以进行反应，从而生成光学活性 2-羟基羧酸 (1)。亚硫酰氯和碱性化合物作用于化合物（1），使其氯化，同时将 2 位的构型反转。这样，一种光学活性的 2-氯羧酸氯化物（5）就产生了。化合物 (5) 经过水解后会生成具有光学活性的 2-氯羧酸 (2)。化合物 (2) 与硫代乙酸盐反应，在其中加入乙酰硫基，同时将 2 位的构型反转，从而生成光学活性 2-乙酰硫代羧酸 (3)。
• PROCESS FOR CRYSTALLIZATION OF 2-ACETYLTHIO-3-PHENYL-PROPIONIC ACID
  申请人：KANEKA CORPORATION

  公开号：EP1275642A1

  公开（公告）日：2003-01-15

  The present invention provides an industrial method for recovering and purifying 2-acetylthio-3-phenylpropionic acid, particularly an optically active 2-acetylthio-3-phenylpropionic acid, as crystals of the free acid. 2-Acetylthio-3-phenylpropionic acid is recovered and purified as crystals of the free acid by using an aliphatic hydrocarbon solvent and/or an aromatic hydrocarbon solvent.

  本发明提供了一种回收和提纯 2-乙酰硫基-3-苯基丙酸，特别是具有光学活性的 2-乙酰硫基-3-苯基丙酸游离酸晶体的工业方法。 使用脂肪烃溶剂和/或芳香烃溶剂可将 2-乙酰硫基-3-苯基丙酸回收并提纯为游离酸晶体。