2-hydroxy-3-phenoxypropyl isobutyrate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-hydroxy-3-phenoxypropyl isobutyrate
• 英文别名: (2-Hydroxy-3-phenoxypropyl) 2-methylpropanoate
• 化学式: C₁₃H₁₈O₄
• 分子量: 238.284
• InChiKey: SIAOZTAXZCENCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  乙酸乙烯酯 、 2-hydroxy-3-phenoxypropyl isobutyrate 以 四氢呋喃 为溶剂， 反应 100.0h， 以42%的产率得到(S)-2-acetoxy-1-(2-methylpropanoyloxy)-3-phenoxypropane
  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 、 异丁酸 在 graphite oxide 作用下， 反应 0.5h， 以20%的产率得到
  参考文献：
  名称：

  氧化石墨催化羧酸与环氧的高效和区域选择性开环

  摘要：

  据报道，在无金属条件下，环氧化物与各种羧酸的有效，简单和区域选择性的开环反应。环氧化物的开环发生在作为有效和可用催化剂的氧化石墨存在下，以高收率生产相应的2-羟基单酯和1,2-二酯衍生物。亲核试剂的区域选择性攻击，较短的反应时间，无金属条件和催化剂的可重复使用性是本方案的优点。

  DOI：

  10.2174/1570178616666190401194252

文献信息

• US20140338550A1
  申请人：——

  公开号：US20140338550A1

  公开（公告）日：2014-11-20
• US8410210B2
  申请人：——

  公开号：US8410210B2

  公开（公告）日：2013-04-02
• Efficient and Regioselective Ring-opening of Epoxides with Carboxylic Acid Catalyzed by Graphite Oxide
  作者：Maryam Mirza-Aghayan、Mahdieh Molaee Tavana、Elaheh Golam Alipour Niazi、Rabah Boukherroub

  DOI：10.2174/1570178616666190401194252

  日期：2020.7.7

  regioselective ring-opening reaction of epoxides with various carboxylic acids under metal-free conditions is reported. The ring-opening of epoxides takes place in the presence of graphite oxide as an efficient and available catalyst to produce the corresponding 2-hydroxy monoester and 1,2-diester derivatives in good yields. Regioselective attack of the nucleophile, short reaction times, metal-free conditions

  据报道，在无金属条件下，环氧化物与各种羧酸的有效，简单和区域选择性的开环反应。环氧化物的开环发生在作为有效和可用催化剂的氧化石墨存在下，以高收率生产相应的2-羟基单酯和1,2-二酯衍生物。亲核试剂的区域选择性攻击，较短的反应时间，无金属条件和催化剂的可重复使用性是本方案的优点。
• 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.