(2S,5R)-2,5-dihydroxy-2-methyl-cyclopentanone | 918403-86-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,5R)-2,5-dihydroxy-2-methyl-cyclopentanone
• 英文别名: (2S,5R)-2-methyl-2,5-dihydroxy-cyclopentanone；(2S,5R)-2,5-Dihydroxy-2-methylcyclopentan-1-one；(2S,5R)-2,5-dihydroxy-2-methylcyclopentan-1-one
• CAS: 918403-86-8
• 化学式: C₆H₁₀O₃
• 分子量: 130.144
• InChiKey: QLVGHVUJYKBZEP-XINAWCOVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  (2S,5R)-2,5-dihydroxy-2-methyl-cyclopentanone 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以52%的产率得到(1S,2S,3R)-1-methyl-cyclopentane-1,2,3-triol
  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
• 作为产物：
  描述：

  (3aS,6aS)-3a-hydroxy-2,2,6a-trimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-one 在 sodium tetrahydroborate 、 硫酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.5h， 生成 (2S,5R)-2,5-dihydroxy-2-methyl-cyclopentanone
  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

• 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.