(1S,4R,6S)-6-hydroxybicyclo[2.2.2]octane-2-one | 150654-18-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,4R,6S)-6-hydroxybicyclo[2.2.2]octane-2-one
• 英文别名: (1S,4R,6S)-6-hydroxy-bicyclo[2.2.2]octan-2-one；(1s,4r,6s)-6-Hydroxy-bicyclo[2.2.2]octane-2-one；(1S,4R,6S)-6-hydroxybicyclo[2.2.2]octan-2-one
• CAS: 150654-18-5
• 化学式: C₈H₁₂O₂
• 分子量: 140.182
• InChiKey: NIRXVBNTTMVMMA-VQVTYTSYSA-N

物化性质

• 沸点：
  268.0±23.0 °C(Predicted)
• 密度：
  1.203±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  bicyclo[2.2.2]octane-2,6-dione 在 nicotinamide adenine dinucleotide phosphate glucose-6-phosphate dehydrogenase 、 Α-D-吡喃葡萄糖6-磷酸 作用下， 以 phosphate buffer 为溶剂， 生成 (1S,4R,6S)-6-hydroxybicyclo[2.2.2]octane-2-one 、 (1R,4S,6S)-bicyclo<2.2.2>octane-6-ol-2-one
  参考文献：
  名称：

  Rationalisation of the substrate concentration dependent diastereoselectivity of a Saccharomyces cerevisiae short-chain dehydrogenase

  摘要：

  The diastereoselectivity of the carbonyl reduction of bicyclo[2.2.2]octane-2,6-dione, catalysed by the purified yeast cytosolic short-chain dehydrogenase Ymr226cp, was shown to be substrate concentration dependent. The changing selectivity was attributed to two distinct binding configurations of the substrate in the active site, each yielding a distinct hydroxy ketone diastereomer. By applying individual K-M and V-max values for each binding configuration, the concentration dependence could be modelled with Michaelis-Menten kinetics and the apparent K-M and V-max values for the generation of each diastereomer determined. This is to the best of our knowledge the first rationalisation of a substrate dependent stereoselectivity for a pro-chiral substrate with an isolated enzyme. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.10.020

文献信息

• Screening of yeast species for the stereo-selective reduction of bicyclo[2.2.2]octane-2,6-dione
  作者：Adriana L. Botes、Daniel Harvig、Martha S. van Dyk、Ian Sarvary、Torbjörn Frejd、Mikael Katz、Bärbel Hahn-Hägerdal、Marie F. Gorwa-Grauslund

  DOI：10.1039/b111064k

  日期：2002.4.9

  Yeast strains from more than 31 different genera were screened for the enantioselective reduction of bicyclo[2.2.2]octane-2,6-dione (1). Reducing activity was found in 80% of the screened yeasts. Bicyclo[2.2.2]octane-2,6-dione was enantioselectively reduced (>98% ee) to (1R,4S,6S)-6-hydroxybicyclo[2.2.2]octane-2-one (−)-2 by 69% of the strains. Enantioselective reduction of the diketone to (1S,4R,6S)-6-hydroxybicyclo[2.2.2]octane-2-one ((+)-3, >98% ee) as a major product is reported for the first time. Candida tropicalis UOFS Y-0534 and Candida wickerhamii UOFS Y-0652 displayed this unusual diastereoselectivity.

  研究人员对31个不同属的酵母菌株进行了筛选，以研究其对双环[2.2.2]辛烷-2,6-二酮（1）的对应选择性还原作用。在筛选的酵母菌株中，有80%具有还原活性。双环[2.2.2]辛烷-2,6-二酮在69%的菌株中发生了对应选择性还原反应（ee>98%），生成（