(1R,2r,3S)-2-methyl-2-(prop-2-enyl)cyclopentane-1,3-diol | 55319-50-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2r,3S)-2-methyl-2-(prop-2-enyl)cyclopentane-1,3-diol
• 英文别名: (1R,2R,3S)-2-allyl-2-methylcyclopentane-1,3-diol
• CAS: 55319-50-1
• 化学式: C₉H₁₆O₂
• 分子量: 156.225
• InChiKey: SROMGZRFQWPRAG-BRPSZJMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.08
• 重原子数：
  11.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (1R,2r,3S)-2-methyl-2-(prop-2-enyl)cyclopentane-1,3-diol 在 环己酮 作用下， 以 正己烷 、 水 为溶剂， 反应 72.0h， 以68%的产率得到(2S,3R)-2-allyl-3-hydroxy-2-methylcyclopentan-1-one
  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
• 作为产物：
  描述：

  2-烯丙基-2-甲基-1,3-环戊二酮 在 二异丁基氢化铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 0.5h， 以67%的产率得到(1R,2s,3S)-2-methyl-2-(prop-2-enyl)cyclopentane-1,3-diol
  参考文献：
  名称：

  A Convergent Total Synthesis of 19-Hydroxysarmentogenin

  摘要：

  DOI：

  10.1002/anie.201302067

文献信息

• Schick, H.; Ballschuh, S.; Welzel, H.-P., Journal fur praktische Chemie (Leipzig 1954), 1991, vol. 333, # 5, p. 749 - 758
  作者：Schick, H.、Ballschuh, S.、Welzel, H.-P.、Schwarz, S.

  DOI：——

  日期：——
• Melchiorre; Pigini; Gualtieri, European Journal of Medicinal Chemistry, 1975, vol. 10, # 6, p. 623 - 627
  作者：Melchiorre、Pigini、Gualtieri、et al.

  DOI：——

  日期：——
• A Convergent Total Synthesis of 19-Hydroxysarmentogenin
  作者：Ken Mukai、Daisuke Urabe、Satoshi Kasuya、Naoto Aoki、Masayuki Inoue

  DOI：10.1002/anie.201302067

  日期：2013.5.10
• Preparation of all stereoisomers of 2-allyl-2-methyl-3-hydroxycyclopentanone by desymmetric processes based on a microbial oxidation and reduction system
  作者：Mikio Fujii、Minoru Takeuchi、Hiroyuki Akita、Kaoru Nakamura

  DOI：10.1016/j.tetlet.2009.06.080

  日期：2009.8

  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.