2,5-dihydroxy-5-methylcyclopent-2-en-1-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,5-dihydroxy-5-methylcyclopent-2-en-1-one
• 英文别名: (5S)-2,5-dihydroxy-5-methylcyclopent-2-en-1-one
• 化学式: C₆H₈O₃
• 分子量: 128.128
• InChiKey: LJGRIUPDNVPIGM-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,2-二甲氧基丙烷 、 (2R,3S)-2,3-二羟基-2-甲氧基-3-甲基环戊酮 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 生成 (3aS,6aS)-3a-hydroxy-2,2,6a-trimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-one 、 2,5-dihydroxy-5-methylcyclopent-2-en-1-one
  参考文献：
  名称：

  Synthesis of chiral hydroxylated cyclopentanones and cyclopentanes

  摘要：

  A method for the synthesis of enantiomeric 1,3-dihydroxy and 2,3-dihydroxy cyclopentanones, starting from a commercially available 3-methyl-cyclopentane-1,2-dione 1, is described. Dione 1 was subjected to asymmetric 3-hydroxylation to afford 3-methyl-3hydroxy-1,2-dione 2. The carbonyl groups in 2 were selectively differentiated by converting them either in dimethylacetal 5 or acetonide 6. Stereoselective reduction of those acetals by using NaBH4 afforded chiral methyl 1,2-dihydroxy cyclopentanone 9 and 1,3-dihydroxy cyclopentanone 10, respectively. The diols obtained were further converted to the corresponding diastereomeric triols 11-13 by hydride reduction. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.09.015

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％）。
• Asymmetric oxidation of 3-alkyl-1,2-cyclopentanediones. Part 1: 3-Hydroxylation of 3-alkyl-1,2-cyclopentanediones
  作者：Anne Paju、Tõnis Kanger、Tõnis Pehk、Aleksander-Mati Müürisepp、Margus Lopp

  DOI：10.1016/s0957-4166(02)00589-x

  日期：2002.11

  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.
• Synthesis of chiral hydroxylated cyclopentanones and cyclopentanes
  作者：Allan Niidu、Anne Paju、Margus Eek、Aleksander-Mati Müürisepp、Tõnis Pehk、Margus Lopp

  DOI：10.1016/j.tetasy.2006.09.015

  日期：2006.10

  A method for the synthesis of enantiomeric 1,3-dihydroxy and 2,3-dihydroxy cyclopentanones, starting from a commercially available 3-methyl-cyclopentane-1,2-dione 1, is described. Dione 1 was subjected to asymmetric 3-hydroxylation to afford 3-methyl-3hydroxy-1,2-dione 2. The carbonyl groups in 2 were selectively differentiated by converting them either in dimethylacetal 5 or acetonide 6. Stereoselective reduction of those acetals by using NaBH4 afforded chiral methyl 1,2-dihydroxy cyclopentanone 9 and 1,3-dihydroxy cyclopentanone 10, respectively. The diols obtained were further converted to the corresponding diastereomeric triols 11-13 by hydride reduction. (c) 2006 Elsevier Ltd. All rights reserved.