(S)-6-chloro-1,2-epoxyhexane

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: (S)-6-chloro-1,2-epoxyhexane
• 英文别名: (2S)-2-(4-chlorobutyl)oxirane
• 化学式: C₆H₁₁ClO
• 分子量: 134.606
• InChiKey: VOUIEAZSNLLDLK-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  8
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  6-氯-1-己烯 在 氧气 、 nicotinamide adenine dinucleotide 、 异丙醇 、 腺嘌呤黄素 作用下， 以 aq. phosphate buffer 为溶剂， 反应 24.0h， 以12.4%的产率得到(S)-6-chloro-1,2-epoxyhexane
  参考文献：
  名称：

  利用来自红球菌属（Rhodococcus sp。）的苯乙烯单加氧酶的生物生产手性环氧烷烃。ST-10（RhSMO）

  摘要：

  AbstractWe describe the enantioselective epoxidation of straight‐chain aliphatic alkenes using a biocatalytic system containing styrene monooxygenase from Rhodococcus sp. ST‐10 and alcohol dehydrogenase from Leifsonia sp. S749. The biocatalyzed enantiomeric epoxidation of 1‐hexene to (S)‐1,2‐epoxyhexane (>44.6 mM) using 2‐propanol as the hydrogen donor was achieved under optimized conditions. The biocatalyst had broad substrate specificity for various aliphatic alkenes, including terminal, internal, unfunctionalized, and di‐ and tri‐substituted alkenes. Here, we demonstrate that this biocatalytic system is suitable for the efficient production of enantioenriched (S)‐epoxyalkanes.magnified image

  DOI：

  10.1002/adsc.201400383

文献信息

• Bioproduction of Chiral Epoxyalkanes using Styrene Monooxygenase from<i>Rhodococcus</i>sp. ST-10 (RhSMO)
  作者：Hiroshi Toda、Ryouta Imae、Nobuya Itoh

  DOI：10.1002/adsc.201400383

  日期：2014.11.3

  AbstractWe describe the enantioselective epoxidation of straight‐chain aliphatic alkenes using a biocatalytic system containing styrene monooxygenase from Rhodococcus sp. ST‐10 and alcohol dehydrogenase from Leifsonia sp. S749. The biocatalyzed enantiomeric epoxidation of 1‐hexene to (S)‐1,2‐epoxyhexane (>44.6 mM) using 2‐propanol as the hydrogen donor was achieved under optimized conditions. The biocatalyst had broad substrate specificity for various aliphatic alkenes, including terminal, internal, unfunctionalized, and di‐ and tri‐substituted alkenes. Here, we demonstrate that this biocatalytic system is suitable for the efficient production of enantioenriched (S)‐epoxyalkanes.magnified image