Acetic acid (S)-1-acetoxymethyl-2-p-tolyloxy-ethyl ester | 147220-35-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: Acetic acid (S)-1-acetoxymethyl-2-p-tolyloxy-ethyl ester
• 英文别名: [(2S)-2-acetyloxy-3-(4-methylphenoxy)propyl] acetate
• CAS: 147220-35-7
• 化学式: C₁₄H₁₈O₅
• 分子量: 266.294
• InChiKey: UJVVUMDDBJJYNP-CQSZACIVSA-N

物化性质

• 沸点：
  377.2±32.0 °C(Predicted)
• 密度：
  1.127±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.87
• 重原子数：
  19.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  乙酸乙烯酯 、 3-(4-甲基苯氧基)-1,2-丙烷二醇 在 cross-linked enzyme aggregate of lipase YCJ₀₁ from Burkholderia ambifaria 作用下， 以 异丙醚 为溶剂， 反应 12.0h， 以99.1%的产率得到
  参考文献：
  名称：

  使用 CLEA-YCJ01 高效拆分 3-芳氧基-1,2-丙二醇，具有高对映选择性†

  摘要：

  来自Burkholderia ambifaria的脂肪酶YCJ01是一种有机溶剂稳定的酶，由于“界面激活”机制，其活性可以被疏水性溶剂激活。以叔丁醇为沉淀剂，脂肪酶YCJ01交联后活性仍提高2.1倍。研究发现，脂肪酶 YCJ01 的交联酶聚集体 (CLEAs-YCJ01) 可通过顺序酯化有效分解 3-(4-甲基苯氧基)-1,2-丙二醇 (MPPD)。使用高底物浓度（180 mmol L-1）实现了对 MPPD 的优异对映选择性（E > 400），S-二乙酸盐的对映体过量 (ee) 值高达 99.2%， R-单乙酸盐的对映体过量 (ee) 值为 99.1% ，并且产率很高 (49.9%) −1 )。由此，同时获得了具有优异ee值的R型和S型化合物，并且通过CLEAs-YCJ01解决了MPPD。CLEAs-YCJ01还表现出较高的操作稳定性，十批次后仍保持91.2%的残留活性。为了进一步评估 CLEAs-YCJ01

  DOI：

  10.1039/c9ra01103j

文献信息

• Kinetic resolution of aliphatic 1,2-diols by a lipase-catalyzed sequential acetylation
  作者：Fritz Theil、Judith Weidner、Sibylle Ballschuh、Annamarie Kunath、Hans Schick

  DOI：10.1016/s0040-4039(00)60573-7

  日期：1993.1

  The kinetic resolution of 13 racemic aliphatic 1,2-diols (rac-1a-m) by means of a lipase-catalyzed sequential acetylation was investigated. The enantioselectivity of the 3-aryloxy-propane-1,2-diols rac-1a-k depends on the substitution pattern at the aryl ring.
• Kinetic resolution of acyclic 1,2-diols using a sequential lipase-catalyzed transesterification in organic solvents
  作者：Fritz Theil、Judith Weidner、Sibylle Ballschuh、Annamarie Kunath、Hans Schick

  DOI：10.1021/jo00081a018

  日期：1994.1

  A method for the kinetic resolution of 3-(aryloxy)-1,2-propanediols rac-1a-n without additional protection-deprotection steps using a lipase-catalyzed sequential transesterification with lipase amnno PS has been developed. In the first step of this one-pot procedure the racemic 1,2-diols are acylated regioselectively at the primary hydroxy group without enantioselection. The subsequent acylation at the secondary hydroxy group of the formed primary monoacetate is responsible for high enantioselection. The enantioselectivity of this transformation depends significantly on the substitution pattern of the aryl ring and the organic solvent used. 3-(Aryloxy)-1,2-propanediols with substituents in the para-position show a much higher enantioselectivity than the corresponding derivatives with ortho-substituents. Among other substrates, the pharmaceuticals Mephenesin, Guaifenesin, and Chlorphenesin have been resolved. The replacement of the aryloxy by alkyl substituent causes a dramatic decrease of enantioselectivity.
• Lipase-catalysed resolution of 3-(aryloxy)-1,2-propanediol derivatives — Towards an improved active site model of Pseudomonas cepacia lipase (amano PS)
  作者：Fritz Theil、Karin Lemke、Sibylle Ballschuh、Annamarie Kunath、Hans Schick

  DOI：10.1016/0957-4166(95)00166-m

  日期：1995.6

  A variety of 3-(aryloxy)-1,2-propanediol derivatives with different substituents on the aromatic ring or at the primary hydroxy group were used as substrates in a kinetic resolution by transesterification with vinyl acetate catalysed by lipase from Pseudomonas cepacia (Amano PS). Derivatives with substituents in the para-position of the aromatic ring were accepted as substrates and resolved with high enantioselectivity. The corresponding derivatives with substituents in the ortho-position were much worse substrates for lipase PS or even non-substrates if the substituent was sufficiently space-filling as found for the tert-butyl, phenyl, benzyl or benzoyl residue. Otherwise, if the primary hydroxy group was substituted by unbranched long-chain acyl residues very good substrates were resulting. In contrast, derivatives with sterically crowded residues at the primary hydroxy group such as the pivaloyl, tert-butyldimethylsilyl, methanesulfonyl, para-toluenesulfonyl or trityl groups were nonsubstrates for lipase PS.