2-hydroxy-3-(2-benzyloxyethyl)-2-cyclopenten-1-one | 514213-30-0

• 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: 2-hydroxy-3-(2-benzyloxyethyl)-2-cyclopenten-1-one
• 英文别名: 2-Hydroxy-3-(2-phenylmethoxyethyl)cyclopent-2-en-1-one；2-hydroxy-3-(2-phenylmethoxyethyl)cyclopent-2-en-1-one
• CAS: 514213-30-0
• 化学式: C₁₄H₁₆O₃
• 分子量: 232.279
• InChiKey: JHGPHPUXONCVGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  2-hydroxy-3-(2-benzyloxyethyl)-2-cyclopenten-1-one 在 titanium(IV) isopropylate 、 L-(+)-酒石酸二乙酯 、 叔丁基过氧化氢 作用下， 以 二氯甲烷 、 癸烷 为溶剂， 反应 48.5h， 以71%的产率得到(R)-2-benzyloxyethyl-5-oxotetrahydrofuran-2-carboxylic acid
  参考文献：
  名称：

  Asymmetric Synthesis of Tertiary 2-Substituted 5-Oxotetrahydrofuran-2-carboxylic Acids

  摘要：

  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.

  DOI：

  10.3987/com-13-s(s)28
• 作为产物：
  描述：

  2-环戊烯基-1-乙酸 在 盐酸 、 sodium hydroxide 、 potassium permanganate 、 lithium aluminium tetrahydride 、 草酰氯 、 sodium hydride 、 二甲基亚砜 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 25.33h， 生成 2-hydroxy-3-(2-benzyloxyethyl)-2-cyclopenten-1-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

文献信息

• Asymmetric oxidation of 3-alkyl-1,2-cyclopentanediones. Part 2: Oxidative ring cleavage of 3-alkyl-1,2-cyclopentanediones: synthesis of 2-alkyl-γ-lactone acids
  作者：Anne Paju、Tõnis Kanger、Tõnis Pehk、Rasmus Lindmaa、Aleksander-Mati Müürisepp、Margus Lopp

  DOI：10.1016/s0957-4166(03)00309-4

  日期：2003.6

  Ti(OiPr)4/diethyl tartrate/tBuOOH system oxidizes 3-alkyl-1,2-cyclopentanediones resulting in hydroxylated ring cleavage products 2-alkyl-γ-lactone acids, in high enantioselectivity (∼95% ee) and satisfactory isolated yields (up to 55%).

  Ti（O i Pr）4 /酒石酸二乙酯/ t BuOOH体系氧化3-烷基-1,2-环戊二酮，生成羟化的环裂解产物2-烷基-γ-内酯酸，对映体选择性高（〜95％ee），令人满意单产（最高55％）。
• 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。
• 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 synthesis of 2-alkyl-substituted 2-hydroxyglutaric acid γ-lactones
  作者：Anne Paju、Marit Laos、Artur Jõgi、Malle Päri、Raissa Jäälaid、Tõnis Pehk、Tõnis Kanger、Margus Lopp

  DOI：10.1016/j.tetlet.2006.04.013

  日期：2006.6

  3-Alkyl-1,2-cyclopentanediones 1 are transformed into 2-alkyl-2-hydroxyglutaric acid gamma-lactones 3 in up to 83% isolated yields and up to 96% ee, affording a simple access to many bioactive compounds, including diacylglycerol lactones (DAG-lactones). (c) 2006 Elsevier Ltd. All rights reserved.
• 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.