1-acetoxy-3-(3-methylphenoxy)propan-2-ol | 204584-12-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-acetoxy-3-(3-methylphenoxy)propan-2-ol
• 英文别名: [2-Hydroxy-3-(3-methylphenoxy)propyl] acetate
• CAS: 204584-12-3
• 化学式: C₁₂H₁₆O₄
• 分子量: 224.257
• InChiKey: XGRRCMGYPUNBON-UHFFFAOYSA-N

物化性质

• 沸点：
  371.7±32.0 °C(predicted)
• 密度：
  1.137±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  1-acetoxy-3-(3-methylphenoxy)propan-2-ol 在 baker's yeast 、 草酰氯 、 sodium phosphate buffer 、 二甲基亚砜 、 三乙胺 、 蔗糖 作用下， 反应 2.83h， 生成 (S)-1-acetoxy-3-(3-methylphenoxy)propan-2-ol
  参考文献：
  名称：

  Baker's yeast mediated stereoselective biotransformation of 1-acetoxy-3-aryloxypropan-2-ones

  摘要：

  A series of 1-acetoxy-3-aryloxypropan-2-ones la-m were synthesized and subjected to biotransformation by baker's yeast yielding optically active monoacetates 5 or ent-5 and/or diols 4 of moderate to excellent enantiomeric purity. The dependence of the reduction/hydrolysis ratio and stereoselectivity on the size and substitution pattern of the aromatic moiety in the substrate is also discussed. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(97)00626-5
• 作为产物：
  描述：

  乙酸乙烯酯 、 间甲苯异氰酸酯 在 porcine pancreatic lipase 作用下， 以 异丙醚 为溶剂， 反应 3.0h， 以98%的产率得到1-acetoxy-3-(3-methylphenoxy)propan-2-ol
  参考文献：
  名称：

  猪胰脂肪酶对3-芳氧基-1,2-丙二醇的区域选择性单乙酰化的生物催化方法

  摘要：

  摘要在为3-芳氧基-1，2-丙二醇的区域选择性单乙酰化而筛选的各种脂肪酶中，发现猪胰脂肪酶的产率更高。通过使用不同的有机溶剂，可以使单乙酰化过程的选择性最大化，二异丙醚转化为单乙酰化产物的转化率最高（约98％）。优化的反应提供了优异的单乙酰化产物收率，并且在原料中存在各种芳基取代基的情况下，在末端羟基处具有区域选择性。 图形概要

  DOI：

  10.1007/s00706-011-0688-y

文献信息

• 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.
• Baker's yeast mediated stereoselective biotransformation of 1-acetoxy-3-aryloxypropan-2-ones
  作者：Gabriella Egri、Attila Kolbert、József Bálint、Elemér Fogassy、Lajos Novák、László Poppe

  DOI：10.1016/s0957-4166(97)00626-5

  日期：1998.1

  A series of 1-acetoxy-3-aryloxypropan-2-ones la-m were synthesized and subjected to biotransformation by baker's yeast yielding optically active monoacetates 5 or ent-5 and/or diols 4 of moderate to excellent enantiomeric purity. The dependence of the reduction/hydrolysis ratio and stereoselectivity on the size and substitution pattern of the aromatic moiety in the substrate is also discussed. (C) 1998 Elsevier Science Ltd. All rights reserved.
• A biocatalytic approach for regioselective monoacetylation of 3-aryloxy-1,2-propanediols by porcine pancreatic lipase
  作者：Vachan Singh Meena、U. C. Banerjee

  DOI：10.1007/s00706-011-0688-y

  日期：2012.6

  AbstractAmong the various lipases screened for the regioselective monoacetylation of 3-aryloxy-1,2-propanediols, porcine pancreatic lipase was found to afford a higher yield. The selectivity for the monoacetylation process was maximized by using different organic solvents and diisopropyl ether gave the highest conversion to monoacetylated product (ca. 98%). The optimized reaction afforded excellent

  摘要在为3-芳氧基-1，2-丙二醇的区域选择性单乙酰化而筛选的各种脂肪酶中，发现猪胰脂肪酶的产率更高。通过使用不同的有机溶剂，可以使单乙酰化过程的选择性最大化，二异丙醚转化为单乙酰化产物的转化率最高（约98％）。优化的反应提供了优异的单乙酰化产物收率，并且在原料中存在各种芳基取代基的情况下，在末端羟基处具有区域选择性。 图形概要