(2-羟基-3-苯氧基丙基)己酸酯 | 68254-53-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: (2-羟基-3-苯氧基丙基)己酸酯
• 英文名称: 2-Hydroxy-3-phenoxypropyl hexanoate
• 英文别名: (2-hydroxy-3-phenoxypropyl) hexanoate
• CAS: 68254-53-5
• 化学式: C₁₅H₂₂O₄
• 分子量: 266.337
• InChiKey: VLLUAMAYUMELJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2-羟基-3-苯氧基丙基)己酸酯 生成 (R)-1-n-hexanoyloxy-3-phenoxy-2-propanol
  参考文献：
  名称：

  Lipase-catalysed resolution of 3-(aryloxy)-1,2-propanediol derivatives — Towards an improved active site model of Pseudomonas cepacia lipase (amano PS)

  摘要：

  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.

  DOI：

  10.1016/0957-4166(95)00166-m
• 作为产物：
  描述：

  苯基缩水甘油醚 、 己酸 生成 (2-羟基-3-苯氧基丙基)己酸酯
  参考文献：
  名称：

  KLEBANOV, M. S.;KIRYAZEV, F. YU.;CHERVINSKIJ, A. YU.;SHOLOGON, I. M., ZH. ORGAN. XIMII, 1984, 20, N 11, 2407-2411

  摘要：

  DOI：

文献信息

• Klebanov, M. S.; Kir'yazev, F. Yu.; Chervinskii, A. Yu., Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, # 11, p. 2193 - 2196
  作者：Klebanov, M. S.、Kir'yazev, F. Yu.、Chervinskii, A. Yu.、Shologon, I. M.

  DOI：——

  日期：——
• 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.
• KLEBANOV, M. S.;KIRYAZEV, F. YU.;CHERVINSKIJ, A. YU.;SHOLOGON, I. M., ZH. ORGAN. XIMII, 1984, 20, N 11, 2407-2411
  作者：KLEBANOV, M. S.、KIRYAZEV, F. YU.、CHERVINSKIJ, A. YU.、SHOLOGON, I. M.

  DOI：——

  日期：——