1-propanoyloxy-1-(3,4-methylenedioxyphenyl)pentane | 5432-27-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 1-propanoyloxy-1-(3,4-methylenedioxyphenyl)pentane
• 英文别名: propionic acid-(1-benzo[1,3]dioxol-5-yl-pentyl ester)；Propionsaeure-(1-benzo[1,3]dioxol-5-yl-pentylester)；1-(1,3-Benzodioxol-5-yl)pentyl propanoate
• CAS: 5432-27-9
• 化学式: C₁₅H₂₀O₄
• 分子量: 264.321
• InChiKey: QAWQEROQKMFDEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-propanoyloxy-1-(3,4-methylenedioxyphenyl)pentane 在 Candida cylindraceae lipase 作用下， 以 phosphate buffer 为溶剂， 反应 16.0h， 生成 1-(3,4-methylenedioxyphenyl)pentanol 、 1-propanoyloxy-1-(3,4-methylenedioxyphenyl)pentane 、 1-propanoyloxy-1-(3,4-methylenedioxyphenyl)pentane
  参考文献：
  名称：

  Trichosporon beigelli esterase (TBE): a versatile esterase for the resolution of economically important racemates

  摘要：

  A hydrolase producing strain Trichosporon beigelli esterase (TBE) isolated from local cottage cheese in its native form has displayed versatility and high efficacy in the kinetic resolution of a wide range of economically important substrates, which include racemic secondary alcohols, such as 1-(6-methoxy-2-naphtliyl)ethanol (E similar to 316), 1-(3,4-methylenedioxyphenyl)ethanol and pentanol (E similar to 180 and 156 resp.), and alkyl esters of carboxylic acids such as ibuprofen (E similar to 340), 2-(benzylthio)propanoic acid (E similar to 1000). In other substrates such as in the primary alcohol 2-(6-methoxy-2-naphthyl)propan-1-ol and carboxylic acids such as 2-(5-bromo-6-methoxy-2-naphthyl)propanoic acid, 2-(2-naphthyloxy)propanoic acid, and substituted 2-thiopropanoic acids, it displayed moderate to low selectivity. Commercial lipases such as CCL, PPL, and PSL were also used in the resolution of the substrates for comparative studies. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.07.009
• 作为产物：
  描述：

  α-丁基胡椒基醇 、 丙酸酐 在 4-二甲氨基吡啶 作用下， 反应 0.08h， 以96.4%的产率得到1-propanoyloxy-1-(3,4-methylenedioxyphenyl)pentane
  参考文献：
  名称：

  Trichosporon beigelli esterase (TBE): a versatile esterase for the resolution of economically important racemates

  摘要：

  A hydrolase producing strain Trichosporon beigelli esterase (TBE) isolated from local cottage cheese in its native form has displayed versatility and high efficacy in the kinetic resolution of a wide range of economically important substrates, which include racemic secondary alcohols, such as 1-(6-methoxy-2-naphtliyl)ethanol (E similar to 316), 1-(3,4-methylenedioxyphenyl)ethanol and pentanol (E similar to 180 and 156 resp.), and alkyl esters of carboxylic acids such as ibuprofen (E similar to 340), 2-(benzylthio)propanoic acid (E similar to 1000). In other substrates such as in the primary alcohol 2-(6-methoxy-2-naphthyl)propan-1-ol and carboxylic acids such as 2-(5-bromo-6-methoxy-2-naphthyl)propanoic acid, 2-(2-naphthyloxy)propanoic acid, and substituted 2-thiopropanoic acids, it displayed moderate to low selectivity. Commercial lipases such as CCL, PPL, and PSL were also used in the resolution of the substrates for comparative studies. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.07.009