(1R,2R)-2-(benz-1,3-oxazol-2-yl)cyclohexan-1-ol | 175610-88-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: (1R,2R)-2-(benz-1,3-oxazol-2-yl)cyclohexan-1-ol
• CAS: 175610-88-5
• 化学式: C₁₃H₁₅NO₂
• 分子量: 217.268
• InChiKey: KVGQSFXQYIYWHT-MWLCHTKSSA-N

物化性质

• 沸点：
  365.9±35.0 °C(Predicted)
• 密度：
  1.222±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.85
• 重原子数：
  16.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  46.26
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1S)-(-)-莰烷酰氯 、 (1R,2R)-2-(benz-1,3-oxazol-2-yl)cyclohexan-1-ol 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 以82%的产率得到2-(benz-1,3-oxazol-2-yl)cyclohex-1-yl-(1S)-camphanoate
  参考文献：
  名称：

  Microbial hydroxylation of 2-cycloalkylbenoxazoles. Part II. Determination of product structures and enhancement of enantiomeric excess

  摘要：

  The determinations of product structures obtained in the microbial hydroxylations of various 2-cycloalkyl-1, 3-benzoxazoles using Cunninghamella blakesleeana DSM 1906 and Bacillus megaterium DSM 32 are described. The initially low e.e. of 3-(benz-1, 3-oxazol-2-yl)cyclopentan-1-ol 6, 2-(benz-1, 3-oxazol-2-yl)cyclohexan-1-ol 14 and 4-(2-bent-1, 3-oxazol-2-yl)cycloheptan-1-ol 21 can be enhanced to 98% using lipase catalyzed resolution.

  DOI：

  10.1016/0957-4166(96)00031-6
• 作为产物：
  描述：

  2-环己基-1,3-苯并恶唑 在 吡啶 、 pseudomonas fluorescens lipase 、 Bacillus megaterium 、 水 、 乙酸酐 作用下， 生成 (1R,2R)-2-(benz-1,3-oxazol-2-yl)cyclohexan-1-ol
  参考文献：
  名称：

  Microbial hydroxylation of 2-cycloalkylbenoxazoles. Part II. Determination of product structures and enhancement of enantiomeric excess

  摘要：

  The determinations of product structures obtained in the microbial hydroxylations of various 2-cycloalkyl-1, 3-benzoxazoles using Cunninghamella blakesleeana DSM 1906 and Bacillus megaterium DSM 32 are described. The initially low e.e. of 3-(benz-1, 3-oxazol-2-yl)cyclopentan-1-ol 6, 2-(benz-1, 3-oxazol-2-yl)cyclohexan-1-ol 14 and 4-(2-bent-1, 3-oxazol-2-yl)cycloheptan-1-ol 21 can be enhanced to 98% using lipase catalyzed resolution.

  DOI：

  10.1016/0957-4166(96)00031-6

文献信息

• Microbial hydroxylation of 2-cycloalkylbenzoxazoles. Part I. Product spectrum obtained from Cunninghamella blakesleeana DSM 1906 and Bacillus megaterium DSM 32
  作者：A. de Raadt、H. Griengl、M. Petsch、P. Plachota、N. Schoo、H. Weber、G. Braunegg、I. Kopper、M. Kreiner、A. Zeiser、K. Kieslich

  DOI：10.1016/0957-4166(96)00030-4

  日期：1996.2

  2-Cycloalkyl-1, 3-benzoxazoles and -thiazoles (ring sizes C-3 to C-8) were biotransformed using the title microorganisms. Products of preparative importance were (1S, 3S)-3-(benz-1, 3-oxazol-2-yl)cyclopentan-1-ol 6, (1R)-3-(benz-1, 3-oxazol-2-yl)cyclopentan-1-one 8, (1R, 2R)-2-(benz-1, 3-oxazol-2-yl)cyclohexan-1-ol 14 and the corresponding cycloheptanol and cycloheptanone derivatives.
• Microbial hydroxylation of 2-cycloalkylbenoxazoles. Part II. Determination of product structures and enhancement of enantiomeric excess
  作者：A. de Raadt、H. Griengl、M. Petsch、P. Plachota、N. Schoo、H. Weber、G. Braunegg、I. Kopper、M. Kreiner、A. Zeiser

  DOI：10.1016/0957-4166(96)00031-6

  日期：1996.2

  The determinations of product structures obtained in the microbial hydroxylations of various 2-cycloalkyl-1, 3-benzoxazoles using Cunninghamella blakesleeana DSM 1906 and Bacillus megaterium DSM 32 are described. The initially low e.e. of 3-(benz-1, 3-oxazol-2-yl)cyclopentan-1-ol 6, 2-(benz-1, 3-oxazol-2-yl)cyclohexan-1-ol 14 and 4-(2-bent-1, 3-oxazol-2-yl)cycloheptan-1-ol 21 can be enhanced to 98% using lipase catalyzed resolution.