[(2R)-1-phenoxypropan-2-yl] butanoate | 174309-44-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: [(2R)-1-phenoxypropan-2-yl] butanoate
• CAS: 174309-44-5
• 化学式: C₁₃H₁₈O₃
• 分子量: 222.284
• InChiKey: HHGHNLAJUQONRU-LLVKDONJSA-N

物化性质

• 沸点：
  291.3±13.0 °C(Predicted)
• 密度：
  1.027±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 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：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [(2R)-1-phenoxypropan-2-yl] butanoate 以 正己烷 为溶剂， 生成 2-氯乙基丁酸酯 、 1-苯氧基-丙醇
  参考文献：
  名称：

  The enantiomer ratio strongly depends on the alkyl part of the acyl donor in transesterification with lipase B from Candida antarctica

  摘要：

  Three secondary alcohols, 1-phenoxy-, 1-phenylmethoxy- and 1-(2-phenylethoxy)-2-propanol, have been resolved by transesterification with the acyl donors 2-chloroethyl butanoate, 2,2,2-trichloroethyl butanoate, vinyl butanoate and butanoic anhydride using lipase B from Candida antarctica as catalyst in hexane. The enantiomer ratio E, which was calculated on the basis of a ping-pong bi-bi mechanism, was highest when 2-chloroethyl butanoate was used as acyl donor, however the reaction was reversible. It was shown that the E-value increased when the amount of 2,2,2-trichloroethyl butanoate was reduced. It is also indicated that butanoic anhydride and vinyl butanoate make the lipase less specific probably by acylation. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00421-1
• 作为产物：
  描述：

  2,2,2-三氯丁酸乙酯 、 1-苯氧基-丙醇 以 正己烷 为溶剂， 生成 [(2R)-1-phenoxypropan-2-yl] butanoate
  参考文献：
  名称：

  The enantiomer ratio strongly depends on the alkyl part of the acyl donor in transesterification with lipase B from Candida antarctica

  摘要：

  Three secondary alcohols, 1-phenoxy-, 1-phenylmethoxy- and 1-(2-phenylethoxy)-2-propanol, have been resolved by transesterification with the acyl donors 2-chloroethyl butanoate, 2,2,2-trichloroethyl butanoate, vinyl butanoate and butanoic anhydride using lipase B from Candida antarctica as catalyst in hexane. The enantiomer ratio E, which was calculated on the basis of a ping-pong bi-bi mechanism, was highest when 2-chloroethyl butanoate was used as acyl donor, however the reaction was reversible. It was shown that the E-value increased when the amount of 2,2,2-trichloroethyl butanoate was reduced. It is also indicated that butanoic anhydride and vinyl butanoate make the lipase less specific probably by acylation. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00421-1

文献信息

• Removal of the acyl donor residue allows the use of simple alkyl esters as acyl donors for the dynamic kinetic resolution of secondary alcohols
  作者：Gerard K.M. Verzijl、Johannes G. de Vries、Quirinus B. Broxterman

  DOI：10.1016/j.tetasy.2005.02.028

  日期：2005.5

  dynamic kinetic resolution of secondary alcohols using a lipase and a ruthenium catalyst as developed by Bäckvall required some improvements to make it suitable for its use in an industrial process. The use of p-chlorophenyl acetate as acyl donor is not desirable in view of the toxicity of the side product. We herein report that simple alkyl esters can be used as acyl donors if the alcohol or ketone residue

  Bäckvall开发的使用脂肪酶和钌催化剂的仲醇动态动力学拆分方法需要进行一些改进，以使其适合工业过程使用。p的使用考虑到副产物的毒性，不希望使用乙酸-氯苯酯作为酰基供体。我们在本文中报道，如果在反应过程中连续除去在酶促酰化过程中形成的醇或酮残基，则可以将简单的烷基酯用作酰基供体。酮的添加加快了外消旋过程，使我们减少了酶和钌催化剂的用量。探索了该方法的范围，并找到了合适范围的酰基供体。使用丁酸异丙酯或苯乙酸甲酯作为酰基供体，使各种苄醇和脂肪醇反应，在大多数情况下，酯的收率> 95％，ee分离为99％。此外，