(R)-5-(2-hydroxyethyl)dihydrofuran-2(3H)-one | 134386-07-5

• 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: (R)-5-(2-hydroxyethyl)dihydrofuran-2(3H)-one
• 英文别名: (R)-5-(2-hydroxyethyl)dihydrofuran-2-one；5-(2-hydroxyethyl)dihydrofuran-2-one；(5R)-5-(2-hydroxyethyl)oxolan-2-one
• CAS: 134386-07-5
• 化学式: C₆H₁₀O₃
• 分子量: 130.144
• InChiKey: DQISCLZSEDAZLX-RXMQYKEDSA-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：

  (R)-5-(2-hydroxyethyl)dihydrofuran-2(3H)-one 在 铬酸 作用下， 生成 (-)-5-methoxycarbonylmethyl-2,,3,4,5-tetrahydrofuran-2-one
  参考文献：
  名称：

  The enzymatic baeyer-villiger oxidation: A study of 4-substituted cyclohexanones

  摘要：

  A study of the enzymatic Baeyer-Villiger oxidation of a number of 4-substituted cyclohexanones utilizing the enzyme cyclohexanone oxygenase (E.C. 1.14.13.-), isolated from the bacteria Acinetobacter NCIB 9871, is described.

  DOI：

  10.1016/s0957-4166(00)80248-7
• 作为产物：
  描述：

  (+)-muconolactone 在 palladium on activated charcoal dimethyl sulfide borane 、 氢气 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 23.0h， 生成 (R)-5-(2-hydroxyethyl)dihydrofuran-2(3H)-one
  参考文献：
  名称：

  恶臭假单胞菌中芳烃生物转化的（+）-松康内酯：产量，绝对构型和对映体纯度。

  摘要：

  据报道，恶臭假单胞菌（Pseudomonas putida）的突变体使外消旋扁桃酸盐生物转化，从而以高收率和对映体纯度得到标题化合物（1）。解决了以前的1绝对构型和相应的甲酯分配中的明显矛盾，从而表明（+）-1具有（5S）立体化学。

  DOI：

  10.1016/s0040-4020(01)87035-6

文献信息

• [EN] NOVEL SIGMA-2 RECEPTOR BINDERS AND THEIR METHOD OF USE<br/>[FR] NOUVEAUX LIANTS DES RÉCEPTEURS SIGMA 2 ET LEUR PROCÉDÉ D'UTILISATION
  申请人：TEMPLE UNIVERSITY-OF THE COMMONWEALTH SYSTEM OF HIGHER EDUCATION

  公开号：WO2016183150A1

  公开（公告）日：2016-11-17

  Pharmaceutical compositions of the invention comprise functionalized lactone derivatives having a disease-modifying action in the treatment of diseases associated with dysregulation of sigma-2 receptor activity.

  本发明的药物组合物包括具有疾病修饰作用的功能化内酯衍生物，在治疗与σ-2受体活性失调相关的疾病中发挥作用。
• A chemoenzymatic approach to (R)-tetrahydro-5-oxo-2-(2-hydroxyethyl)furan, a useful chiral synthon: Application to the synthesis of (S)-4-hexanolide, pheromone antipode of .
  作者：S.K. Ghosh、S. Chattopadhyay、V.R. Mamdapur

  DOI：10.1016/s0040-4020(01)96037-5

  日期：1991.5

  A synthesis of versatile chiral synthon 6 has been accomplished via a baker's yeast mediated reduction, which was further utilized for the synthesis of 8, pheromone antipode of stored grain pest.

  多功能手性合成子6的合成已通过面包酵母的介导还原反应完成，该还原反应还用于合成8种储存的谷物害虫的信息素对映体。
• Enantio- and diastereoselective synthesis of erysulfone and erysulfoxide
  作者：Laurence Bourdeau、Alan G. Sutherland

  DOI：10.1016/s0040-4039(97)10440-3

  日期：1997.12

  The natural products erysulfone (1) and erysulfoxide (2) have been prepared from (+)-muconolactone (3). This synthetic work has substantiated the earlier, probable assignment of absolute configuration of these targets.

  从（+）-粘康内酯（3）制备了天然产物异硫酮（1）和异硫氧化物（2）。这项综合工作证实了这些目标的绝对配置的早期，可能的分配。
• 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.