(R)-4-oxocyclopenten-2-enyl 2-phenylacetate | 1391630-29-7

• 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: (R)-4-oxocyclopenten-2-enyl 2-phenylacetate
• 英文别名: (R)-oxocyclopent-2-enyl 2-phenylacetate；[(1R)-4-oxocyclopent-2-en-1-yl] 2-phenylacetate
• CAS: 1391630-29-7
• 化学式: C₁₃H₁₂O₃
• 分子量: 216.236
• InChiKey: GSDFKFYANJXFHI-LBPRGKRZSA-N

物化性质

• 沸点：
  355.2±42.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-4-oxocyclopenten-2-enyl 2-phenylacetate 在 水 作用下， 以 叔丁醇 为溶剂， 反应 10.0h， 以93%的产率得到4-羟基-2-环戊烯酮
  参考文献：
  名称：

  Synthesis of Enantiomerically Pure 4-Hydroxy-2-cyclopentenones

  摘要：

  Conversion of furfuryl alcohol to 4-hydroxy-2-cyclopentenone was studied in a microreactor channel of 0.5 mm diameter and 1.5 m length. Addition of 1 M N-methylpyrrolidinone as a cosolvent significantly reduces the polymeric material normally formed during the reaction in purely aqueous solution. The reaction follows pseudo-first-order kinetics at constant pressure (200 bar) with the values of Delta H-double dagger = 18 +/- 2 kcal/mol and Delta S-double dagger = -38 +/- 3 cal/mol/K. At 240 degrees C, 200 bar pressure, and residence time of 1.5 min, the product is obtained with 98% conversion and is isolated as a stable O-phenylacetyl derivative in 80% yield. This racemic mixture was resolved into enantiomerically pure forms by kinetic resolution with penicillin G acylase (E.C.3.5.1.11) immobilized on epoxy-activated polymer in 90-92% theoretical yield and >99% ee.

  DOI：

  10.1021/op400266k
• 作为产物：
  描述：

  4-羟基-2-环戊烯酮 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 3.0h， 生成 (R)-4-oxocyclopenten-2-enyl 2-phenylacetate
  参考文献：
  名称：

  Resolution of racemic 4-hydroxy-2-cyclopentenone with immobilized penicillin G acylase

  摘要：

  Enantiomerically pure 4-oxo-2-cyclopentenyl derivatives were prepared by kinetic resolution with penicillin G acylase (EC 3.5.1.11) immobilized on an epoxy activated polymer. The enzyme selectively hydrolyzes the phenylacetyl ester of the (S)-enantiomer to give the (S)-alcohol. The enantioselectivity E increases from 12.4 in 0.05 M phosphate buffer, to E = 100-110 in acetonitrile-buffer (20% v/v) and E >200 in diisopropyl ether. The immobilized enzyme is stable and retains >90% of its activity after 10 recycles over one week at room temperature. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.05.018

文献信息

• Synthesis of Enantiomerically Pure 4-Hydroxy-2-cyclopentenones
  作者：Thenkrishnan Kumaraguru、Panuganti Babita、Gurrala Sheelu、Kuna Lavanya、Nitin W. Fadnavis

  DOI：10.1021/op400266k

  日期：2013.12.20

  Conversion of furfuryl alcohol to 4-hydroxy-2-cyclopentenone was studied in a microreactor channel of 0.5 mm diameter and 1.5 m length. Addition of 1 M N-methylpyrrolidinone as a cosolvent significantly reduces the polymeric material normally formed during the reaction in purely aqueous solution. The reaction follows pseudo-first-order kinetics at constant pressure (200 bar) with the values of Delta H-double dagger = 18 +/- 2 kcal/mol and Delta S-double dagger = -38 +/- 3 cal/mol/K. At 240 degrees C, 200 bar pressure, and residence time of 1.5 min, the product is obtained with 98% conversion and is isolated as a stable O-phenylacetyl derivative in 80% yield. This racemic mixture was resolved into enantiomerically pure forms by kinetic resolution with penicillin G acylase (E.C.3.5.1.11) immobilized on epoxy-activated polymer in 90-92% theoretical yield and >99% ee.
• Resolution of racemic 4-hydroxy-2-cyclopentenone with immobilized penicillin G acylase
  作者：Thenkrishnan Kumaraguru、Nitin W. Fadnavis

  DOI：10.1016/j.tetasy.2012.05.018

  日期：2012.5

  Enantiomerically pure 4-oxo-2-cyclopentenyl derivatives were prepared by kinetic resolution with penicillin G acylase (EC 3.5.1.11) immobilized on an epoxy activated polymer. The enzyme selectively hydrolyzes the phenylacetyl ester of the (S)-enantiomer to give the (S)-alcohol. The enantioselectivity E increases from 12.4 in 0.05 M phosphate buffer, to E = 100-110 in acetonitrile-buffer (20% v/v) and E >200 in diisopropyl ether. The immobilized enzyme is stable and retains >90% of its activity after 10 recycles over one week at room temperature. (C) 2012 Elsevier Ltd. All rights reserved.