5-(2-hydroxyethyl)dihydrofuran-2-one | 108380-23-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 5-(2-hydroxyethyl)dihydrofuran-2-one
• 英文别名: S-Hydroxyethyl-γ-butyrolactone；(S)-5-(2-hydroxyethyl)dihydrofuran-2-one；(5S)-5-(2-hydroxyethyl)oxolan-2-one
• CAS: 108380-23-0
• 化学式: C₆H₁₀O₃
• 分子量: 130.144
• InChiKey: DQISCLZSEDAZLX-YFKPBYRVSA-N

物化性质

• 沸点：
  301.8±15.0 °C(Predicted)
• 密度：
  1.168±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(2-hydroxyethyl)dihydrofuran-2-one 在 吡啶 、 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile 、 三正丁基氢锡 、 sodium iodide 作用下， 以 丙酮 、 苯 为溶剂， 反应 18.5h， 生成 4-hexanolide
  参考文献：
  名称：

  Gurjar, Mukund K.; Patil, Vijay J., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1986, vol. 25, p. 596 - 599

  摘要：

  DOI：
• 作为产物：
  描述：

  3-deoxy-1,2;5,6-di-O-isopropylidene-α-D-glucofuranoside 在 palladium on activated charcoal 吡啶 、 盐酸 、 硫酸 、 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile 、 氢气 、 双氧水 、 三正丁基氢锡 、 sodium acetate 、 sodium hydride 、 溶剂黄146 、 pyridinium chlorochromate 、 sodium iodide 、 diborane(6) 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 甲苯 、 丁酮 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 89.5h， 生成 5-(2-hydroxyethyl)dihydrofuran-2-one
  参考文献：
  名称：

  Gurjar, Mukund K.; Patil, Vijay J., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1986, vol. 25, p. 596 - 599

  摘要：

  DOI：

文献信息

• New Bioorganic Reagents:  Evolved Cyclohexanone MonooxygenaseWhy Is It More Selective?
  作者：Margaret M. Kayser、Christopher M. Clouthier

  DOI：10.1021/jo061349t

  日期：2006.10.1

  Four mutants of the cyclohexanone monooxygenase (CHMO) evolved as catalysts for Baeyer-Villiger oxidation of 4-hydroxycyclohexanone were investigated as catalysts for a variety of 4-substituted and 4,4-disubstituted cyclohexanones. Several excellent catalytic matches (mutant/substrate) were identified. The most important, however, is the finding that, in a number of cases, a mutant with a single exchange, Phe432Ser, was shown to be as robust and more selective as a catalyst than the wild-type CHMO. All biotransformations were performed on a laboratory scale, allowing full characterization of the products. The absolute configurations of two products were established. A model suggesting a possible role of the 432 serine residue in enantioselectivity control is proposed.
• Increasing the enantioselectivity of cyclopentanone monooxygenase (CPMO): profile of new CPMO mutants
  作者：Christopher M. Clouthier、Margaret M. Kayser

  DOI：10.1016/j.tetasy.2006.10.001

  日期：2006.10

  A series of cyclohexanones substituted at the 4-position with a selection of hydrophobic and hydrophilic groups were used as substrates in the evaluation of six new cyclopentanone monooxygenase (CPMO) mutants. These mutants were obtained through evolutionary modifications in two specific regions of the CPMO's putative active site. Several mutant enzymes with improved enantioselectivity were identified. Analysis of the results, in terms of a diamond model, illustrates how a family of cyclohexanone substrates may be used to explore putative active sites of Baeyer-Villiger monooxygenases (BVMOs) and to design productive mutations for specific substrates. (c) 2006 Elsevier Ltd. All rights reserved.
• Directed Evolution as a Method To Create Enantioselective Cyclohexanone Monooxygenases for Catalysis in Baeyer–Villiger Reactions
  作者：Manfred T. Reetz、Birgit Brunner、Toni Schneider、Frank Schulz、Christopher M. Clouthier、Margaret M. Kayser

  DOI：10.1002/anie.200460272

  日期：2004.8.6
• Gurjar, Mukund K.; Patil, Vijay J., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1986, vol. 25, p. 596 - 599
  作者：Gurjar, Mukund K.、Patil, Vijay J.

  DOI：——

  日期：——