Ethyl 4-[5-[butanoyloxy(cyano)methyl]furan-2-yl]benzoate | 601464-33-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Ethyl 4-[5-[butanoyloxy(cyano)methyl]furan-2-yl]benzoate
• 英文别名: ethyl 4-[5-[butanoyloxy(cyano)methyl]furan-2-yl]benzoate
• CAS: 601464-33-9
• 化学式: C₁₉H₁₉NO₅
• 分子量: 341.364
• InChiKey: QKMBSLCVXYIIJO-UHFFFAOYSA-N

物化性质

• 沸点：
  460.0±45.0 °C(Predicted)
• 密度：
  1.183±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  89.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Ethyl 4-[5-[butanoyloxy(cyano)methyl]furan-2-yl]benzoate 在 甲醇 、 Pseudomonas cepacia lipase 作用下， 以 甲苯 为溶剂， 反应 144.0h， 生成 4-[5-((R)-Cyano-hydroxy-methyl)-furan-2-yl]-benzoic acid ethyl ester 、 4-[5-((S)-Cyano-hydroxy-methyl)-furan-2-yl]-benzoic acid ethyl ester 、 4-[5-((S)-Butyryloxy-cyano-methyl)-furan-2-yl]-benzoic acid ethyl ester 、 4-[5-((R)-Butyryloxy-cyano-methyl)-furan-2-yl]-benzoic acid ethyl ester
  参考文献：
  名称：

  Preparation of novel phenylfuran-based cyanohydrin esters: lipase-catalysed kinetic and dynamic resolution

  摘要：

  A series of novel (R)-5-phenylfuran-2-yl cyanomethyl butanoates were prepared by Pseudomonas cepacia lipase-catalysed dynamic kinetic resolution in toluene. The method exploits a basic resin both for the racemization and formation of phenylfuran-based cyanohydrins and for the decomposition of acetone cyanohydrin in one-pot with enzymatic enantio selective acylation using vinyl butanoate. The lipase-catalysed methanolysis of racemic 5-phenylfuran-2-yi cyanomethyl butanoates in toluene with E much greater than100 was shown to be usable when the corresponding (S)-butanoates are needed. Candida antarctica lipase A provided racemic cyanohydrin butanoates with quantitative chemical yields under mild conditions. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00286-6
• 作为产物：
  描述：

  5-甲酰基-2-呋喃基苯甲酸乙酯 在 盐酸 、 Candida antarctica Lipase A 、 zinc(II) iodide 作用下， 以 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 3.0h， 生成 Ethyl 4-[5-[butanoyloxy(cyano)methyl]furan-2-yl]benzoate
  参考文献：
  名称：

  Preparation of novel phenylfuran-based cyanohydrin esters: lipase-catalysed kinetic and dynamic resolution

  摘要：

  A series of novel (R)-5-phenylfuran-2-yl cyanomethyl butanoates were prepared by Pseudomonas cepacia lipase-catalysed dynamic kinetic resolution in toluene. The method exploits a basic resin both for the racemization and formation of phenylfuran-based cyanohydrins and for the decomposition of acetone cyanohydrin in one-pot with enzymatic enantio selective acylation using vinyl butanoate. The lipase-catalysed methanolysis of racemic 5-phenylfuran-2-yi cyanomethyl butanoates in toluene with E much greater than100 was shown to be usable when the corresponding (S)-butanoates are needed. Candida antarctica lipase A provided racemic cyanohydrin butanoates with quantitative chemical yields under mild conditions. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00286-6

文献信息

• Preparation of novel phenylfuran-based cyanohydrin esters: lipase-catalysed kinetic and dynamic resolution
  作者：Csaba Paizs、Petri Tähtinen、Katri Lundell、László Poppe、Florin-Dan Irimie、Liisa T. Kanerva

  DOI：10.1016/s0957-4166(03)00286-6

  日期：2003.7

  A series of novel (R)-5-phenylfuran-2-yl cyanomethyl butanoates were prepared by Pseudomonas cepacia lipase-catalysed dynamic kinetic resolution in toluene. The method exploits a basic resin both for the racemization and formation of phenylfuran-based cyanohydrins and for the decomposition of acetone cyanohydrin in one-pot with enzymatic enantio selective acylation using vinyl butanoate. The lipase-catalysed methanolysis of racemic 5-phenylfuran-2-yi cyanomethyl butanoates in toluene with E much greater than100 was shown to be usable when the corresponding (S)-butanoates are needed. Candida antarctica lipase A provided racemic cyanohydrin butanoates with quantitative chemical yields under mild conditions. (C) 2003 Elsevier Science Ltd. All rights reserved.

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