| 74498-01-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• CAS: 74498-01-4
• 化学式: C₁₁H₁₆O₃
• 分子量: 196.246
• InChiKey: AQIOAAFNXRHYKQ-GHMZBOCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.86
• 重原子数：
  14.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  乙酸酐 、 (2S,3R)-2-allyl-3-hydroxy-2-methylcyclopentan-1-one 在 吡啶 作用下， 生成
  参考文献：
  名称：

  Preparation of all stereoisomers of 2-allyl-2-methyl-3-hydroxycyclopentanone by desymmetric processes based on a microbial oxidation and reduction system

  摘要：

  All stereoisomers of 2-allyl-3-hydroxy-2-methylcyclopentanones 2-5 were prepared in high conversion and in an optically pure form by microbial reduction and oxidation. The reduction of symmetric diketone 1 by Geotrichum candidum NBRC 4597 under anaerobic conditions gave 2 in 83% yield (98% conversion), >99% de, and >99% ee, whereas the reduction of 1 by G. candidum NBRC 5767 under aerobic conditions gave 3 in 75% yield (99% conversion), >99% de, and >99% ee. Oxidation of meso-diol 6 by G. candidum NBRC 5767 under aerobic conditions afforded 4 in 83% yield (99% conversion) and >99% ee, while oxidation of meso-diol 7 by Mucor heimalis IAM 6095 in the presence of cyclohexanone as a co-oxidant afforded 5 in 68% yield (75% conversion) and >99% ee. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.06.080