2-羟基-3-(2-羟基乙基)环戊-2-烯-1-酮 | 303183-80-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-羟基-3-(2-羟基乙基)环戊-2-烯-1-酮
• 英文名称: 2-hydroxy-3-(2-hydroxyxyethyl)cyclopent-2-en-1-one
• 英文别名: 2-hydroxy-3-(2-hydroxyethyl)-2-cyclopenten-1-one；2-hydroxy-3-(2-hydroxyethyl)cyclopent-2-en-1-one；2-Cyclopenten-1-one, 2-hydroxy-3-(2-hydroxyethyl)-
• CAS: 303183-80-4
• 化学式: C₇H₁₀O₃
• 分子量: 142.155
• InChiKey: NRYABLFNRBOMDT-UHFFFAOYSA-N

物化性质

• 沸点：
  341.0±42.0 °C(Predicted)
• 密度：
  1.334±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-羟基-3-(2-羟基乙基)环戊-2-烯-1-酮 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 (+)-Weinsaeure-diethylester 作用下， 以 二氯甲烷 为溶剂， 反应 42.0h， 以25%的产率得到1,5-dihydroxy-2-oxabicyclo[3.3.0]octane-8-one
  参考文献：
  名称：

  Asymmetric oxidation of 3-alkyl-1,2-cyclopentanediones. Part 1: 3-Hydroxylation of 3-alkyl-1,2-cyclopentanediones

  摘要：

  3-Alkyl-1,2-cyclopentanediones undergo asymmetric 3-hydroxylation with the Sharpless Ti-complex resulting in enantiomeric 3-hydroxy carbonyl compounds with ee up to 95% in yields of 22-40%. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00589-x
• 作为产物：
  描述：

  2-环戊烯基-1-乙酸 在 咪唑 、 盐酸 、 sodium hydroxide 、 potassium permanganate 、 lithium aluminium tetrahydride 、 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 47.33h， 生成 2-羟基-3-(2-羟基乙基)环戊-2-烯-1-酮
  参考文献：
  名称：

  Asymmetric oxidation of 3-alkyl-1,2-cyclopentanediones. Part 1: 3-Hydroxylation of 3-alkyl-1,2-cyclopentanediones

  摘要：

  3-Alkyl-1,2-cyclopentanediones undergo asymmetric 3-hydroxylation with the Sharpless Ti-complex resulting in enantiomeric 3-hydroxy carbonyl compounds with ee up to 95% in yields of 22-40%. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00589-x

文献信息

• Aerobic cascade oxidation of substituted cyclopentane-1,2-diones using metalloporphyrin catalysts
  作者：Karolin Maljutenko、Victor Borovkov、Dzmitry Kananovich、Ivar Järving、Margus Lopp

  DOI：10.1016/j.tet.2017.12.009

  日期：2018.2

  A method for the aerobic cascade oxidation of cyclopentane-1,2-diones using metal porphyrins as catalysts, yielding hydroxydiacids 2, ketoacid 3 and diketoacids 4 which are the intermediates of important biologically active compounds is reported. This method is operationally simple and can be employed under ambient conditions.

  报道了一种使用金属卟啉作为催化剂的有氧级联环戊烷-1,2-二酮的有氧级联氧化的方法，该方法产生作为重要的生物活性化合物的中间体的羟基二酸2，酮酸3和二酮酸4。该方法操作简单，可以在环境条件下使用。
• Asymmetric Synthesis of Tertiary 2-Substituted 5-Oxotetrahydrofuran-2-carboxylic Acids
  作者：Margus Lopp、Anne Paju、Karolin Oja、Katharina Matkevitš、Priit Lumi、Ivar Järving、Tõnis Pehk

  DOI：10.3987/com-13-s(s)28

  日期：——

  3-Substituted 1,2-cyclopentanediones 1 were transformed to 2-substituted 5-oxotetrahydrofuran-2-carboxylic acids 2 using a catalytic process with 0.2-0.3 equivalent of Ti(OiPr)(4)/tartaric ester/tBuO0H complex in up to 72% isolated yield and up to 94% ee. Different functional groups in the 3-alkyl substituent of 1 like, hydroxy, ether, Boc-amino and ester groups are tolerated. Boc-aminomethyl substitu.ents lead to beta-amino acid analogues and Boc-aminoethyl substituent to gamma-amino acid analogues as well as spiro-lactonelactams. A direct, two-step procedure for homocitric acid synthesis is described.
• Heterogeneous platinum catalytic aerobic oxidation of cyclopentane-1,2-diols to cyclopentane-1,2-diones
  作者：Indrek Reile、Sigrid Kalle、Franz Werner、Ivar Järving、Marina Kudrjashova、Anne Paju、Margus Lopp

  DOI：10.1016/j.tet.2014.03.104

  日期：2014.6

  A method for the aerobic oxidation of cyclopentane-1,2-diols to the corresponding diketones over a commercial heterogeneous Pt/C catalyst is described. Unsubstituted and 3- or 4-substituted cyclopentane-1,2-diols are oxidized to 1,2-dicarbonyl compounds in good yields under the reported optimized reaction conditions (atmospheric air, 1 mol % of catalyst, 1 equiv of LiOH, aqueous solvents and 60 degrees C temperature). The method is applicable for producing cyclopentane-1,2-diketones in a scalable manner. (C) 2014 Elsevier Ltd. All rights reserved.
• Asymmetric oxidation of 1,2-cyclopentanediones
  作者：Anne Paju、Tõnis Kanger、Tõnis Pehk、Margus Lopp

  DOI：10.1016/s0040-4039(00)01106-0

  日期：2000.8

  Cyclic 3-alkyl-1,2-cyclopentanediones undergo a direct asymmetric oxidation with the DET/Ti(OiPr)(4)/tBuOOH oxidative system, resulting in enantiomeric alpha-hydroxy compounds and ring-cleaved hydroxylated acids (lactones) up to 95% ee. (C) 2000 Elsevier Science Ltd. All rights reserved.
• ESTERS OF (2-HYDROXY-3-OXO-CYCLOPENT-1-ENYL) ACETIC ACID AND THEIR USE FOR PREPARING (-)-R-HOMOCITRIC ACID GAMMA-LACTONE, (+)-S-HOMOCITRIC ACID GAMMA-LACTONE AND THE CORRESPONDING (-)-R-HOMOCITRIC ACID AND (+)-S-HOMOCITRIC ACID SALTS
  申请人：Lopp Margus

  公开号：US20090187041A1

  公开（公告）日：2009-07-23

  Archiral (2-hydroxy-3-oxo-cyclopent-1-enyl) acetic acid) alkyl, alkylphenyl and phenyl esters, and a simple and efficient method for the synthesis of both enantiomers of homocitric acid gamma-lactone and the corresponding salts from these esters are described. The method is based on asymmetric oxidation of esters, and the steps of basic and acidic hydrolysis and final acidic lactonization of the homocitric acid into homocitric acid gamma-lactone. The homocitric acid salts are obtained after basic treatment of homocitric acid gamma-lactone. The esters, conditions and reagents used in chemical conversion and separating products are important constituents affording efficient and simple method for production of homocitric acid gamma-lactone and homocitric acid salts.