(2S)-2-hydroxy-5,5-dimethoxy-2-methyl-cyclopentanone | 918403-81-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S)-2-hydroxy-5,5-dimethoxy-2-methyl-cyclopentanone
• 英文别名: (2S)-2-hydroxy-5,5-dimethoxy-2-methylcyclopentan-1-one
• CAS: 918403-81-3
• 化学式: C₈H₁₄O₄
• 分子量: 174.197
• InChiKey: ZHYYVYAXLRHHOS-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S)-2-hydroxy-5,5-dimethoxy-2-methyl-cyclopentanone 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.25h， 以73.5%的产率得到(1S,2R)-3,3-dimethoxy-1-methyl-cyclopentane-1,2-diol
  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：

  甲醇 、 (2R,3S)-2,3-二羟基-2-甲氧基-3-甲基环戊酮 在 三氟化硼乙醚 作用下， 反应 26.0h， 以49%的产率得到(2S)-2-hydroxy-5,5-dimethoxy-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.