(R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1S,2S)-2-(4-methoxy-benzyl)-cyclohexyl ester | 112066-35-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1S,2S)-2-(4-methoxy-benzyl)-cyclohexyl ester
• CAS: 112066-35-0
• 化学式: C₂₄H₂₇F₃O₄
• 分子量: 436.471
• InChiKey: GYKMBUKEUBOOIS-AVCGJXAMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.44
• 重原子数：
  31.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  cis-2-(4-methoxybenzyl)cyclohexyl acetate 在 phosphate buffer 、 immobilized Novozyme 435 、 1-丁基-4-甲基氯化吡啶鎓 作用下， 反应 72.0h， 生成 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1S,2S)-2-(4-methoxy-benzyl)-cyclohexyl ester
  参考文献：
  名称：

  Application of ionic liquids in enzymic resolution by hydrolysis of cycloalkyl acetates

  摘要：

  A comparative study was performed in the enzymic resolution of the isomers of 2-(4-methoxybenzyl)cyclohexyl acetates 1 and 2. The investigation consisted in application of three commercially available lipases (Novozyme 435, Lipozyme IM and non-immobilized powdered lipase from Candida antarctica), two ionic liquids (1-butyl-4-methylpyridinium chloride and 1,3-dimethylimidazolinium methyl sulfate), three modifications of the reaction conditions and two respective isomers of the racemic substrate (1 and 2), and resulted in our finding the appropriate conditions to get both of the products, stereoisomers of 2-(4-methoxybenzyl)cyclohexanol (3; 1S,2S) or (5; 1S,2R), and (in some cases) also the stereoisomers of the deracemized substrate (4; 1 R,2R) or (6; 1 R,2S) with high or acceptable enantiomeric purity. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.10.045

文献信息

• Insect pest control agents: Novel chiral butanoate esters (juvenogens)
  作者：Zdeněk Wimmer、Alexandra J.F.D.M. Floro、Marie Zarevúcka、Martina Wimmerová、Guido Sello、Fulvia Orsini

  DOI：10.1016/j.bmc.2007.06.043

  日期：2007.9

  chiral resolution of the respective racemic cis- and trans-isomers of 2-(4-methoxybenzyl)cyclohexanol either directly or after a subsequent chemical esterification of the chiral precursor. In this synthesis, two convenient butanoic acid activating esters, vinyl butanoate and 2,2,2-trifluoroethyl butanoate, were employed, and the chiral precursors in the synthesis of the target molecules were obtained in

  在研究生物活性醇的酯衍生物（幼虫，生物化学活化的昆虫激素化合物）并可能在昆虫有害生物防治中应用的过程中，需要使用所有现有的乙基N- 2- [4-（2-丁酸酰氧基环己基）立体异构体发生了甲基]苯氧基}乙基氨基甲酸酯。由它们的手性前体，即2-（4-甲氧基苄基）环己基丁酸酯的相应立体异构体，通过除去它们的保护基（甲基），以及随后将芳族羟基部分与N-（2-溴乙基）氨基甲酸乙酯缩合而合成。直接或在制备后，通过念珠菌南极脂肪酶介导的2-（4-甲氧基苄基）环己基丁酸酯的对映异构体的手性拆分和手性拆分2-（4-甲氧基苄基）环己醇的外消旋顺式和反式异构体，获得了所需的2-（4-甲氧基苄基）环己基丁酸酯对映异构体。手性前体的后续化学酯化。在该合成中，使用了两种方便的丁酸活化酯，丁酸乙烯酯和2,2,2-三氟乙基丁酸酸酯，并以41-48％的收率获得了目标分子合成中的手性前体（即82- 96％的转化率）和对映体纯度ee
• Wimmer, Zdenek; Budesinsky, Milos; Macek, Tomas, Collection of Czechoslovak Chemical Communications, 1987, vol. 52, # 9, p. 2326 - 2337
  作者：Wimmer, Zdenek、Budesinsky, Milos、Macek, Tomas、Svatos, Ales、Saman, David、et.al.

  DOI：——

  日期：——