(1S,3S)-3-(1,3-苯并恶唑-2-基)环戊烷-1-醇 | 175610-82-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 中文名称: (1S,3S)-3-(1,3-苯并恶唑-2-基)环戊烷-1-醇
• 英文名称: (1S,3S)-3-(benz-1,3-oxazol-2-yl)cyclopentan-1-ol
• 英文别名: (1S,3S)-3-(1,3-Benzoxazol-2-yl)cyclopentan-1-ol
• CAS: 175610-82-9
• 化学式: C₁₂H₁₃NO₂
• 分子量: 203.241
• InChiKey: BWDCTHGTAICVPP-IUCAKERBSA-N

物化性质

• 沸点：
  351.7±35.0 °C(Predicted)
• 密度：
  1.270±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  46.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,3S)-3-(1,3-苯并恶唑-2-基)环戊烷-1-醇 在 sodium methylate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 28.0h， 生成 (1R,3S)-3-(1,3-benzoxazol-2-yl)cyclopentan-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
• 作为产物：
  描述：

  2-cyclopentyl-1,3-benzoxazole 在 吡啶 、 Bacillus megaterium 、 Pseudomonas fluorescence lipase 、 水 、 乙酸酐 作用下， 生成 (1S,3S)-3-(1,3-苯并恶唑-2-基)环戊烷-1-醇
  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

• Stereoselective hydroxylation of an achiral cyclopentanecarboxylic acid derivative using engineered P450s BM-3
  作者：Dieter F. Münzer、Peter Meinhold、Matthew W. Peters、Sabine Feichtenhofer、Herfried Griengl、Frances H. Arnold、Anton Glieder、Anna de Raadt

  DOI：10.1039/b501527h

  日期：——

  Substrate engineered, achiral carboxylic acid derivative 2 was biohydroxylated with various mutants of cytochrome P450 BM-3 to give two out of the four possible diastereoisomers in high de and ee. The BM-3 mutants exhibit up to 9200 total turnovers for hydroxylation of the engineered substrate, which without the protecting group is not transformed by this enzyme.

  通过生物羟基化，将底物工程化的无手性羧酸衍生物2与细胞色素P450 BM-3的各种突变体结合，在四种可能的非对映异构体中，有二种异构体的对映选择性（de）和立体选择性（ee）较高。BM-3突变体对工程化底物的羟基化总转化率高达9200，而如果没有保护基团，这种酶就无法对其进行转化。
• 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.