(-)-diethyl 2-((1S,3S)-3-hydroxycyclohexyl)malonate | 1224876-85-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (-)-diethyl 2-((1S,3S)-3-hydroxycyclohexyl)malonate
• CAS: 1224876-85-0
• 化学式: C₁₃H₂₂O₅
• 分子量: 258.315
• InChiKey: MAIYFWBSCJLJKV-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.28
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  72.83
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (-)-diethyl 2-((1S,3S)-3-hydroxycyclohexyl)malonate 在 potassium hydroxide 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 生成 2-[(1S,3S)-3-hydroxycyclohexyl]acetic acid
  参考文献：
  名称：

  Chemoenzymatic synthesis of 2-oxabicyclo[3.3.1]nonan-3-one enantiomers via microbial reduction by Absidia coerulea AM 93

  摘要：

  Microbial enantioselective reduction of (+/-)-diethyl 2-(3-oxocyclohexyl)malonate (1) has been described. A screening test oil twenty-four fungi strains was carried Out. Most of the microorganisms preferred bioreduction of (+)-isomer of delta-ketoester (1) to (+)-trans delta-hydroxy ester (2) with the anti-Prelog selectivity. Biotransformation conditions using Absidia coerulea AM 93 were optimized with respect to the growth medium, temperature and pH. An effect of 48 chemical additives oil the Course of biotransformation was checked. (-)-Diethyl 2-((S)-3-oxocyclohexyl)malonate ((-)-1) (ee=98%) and (+)-diethyl 2-((1R, 3R)-3-hydroxycyclohexyl)malonate ((+)-2) (ee=99%)were isolated and subjected to chemical lactonization, leading to (+)-(1R, 5S)-2-oxabicyclo[3.3.1]nonan-3-one ((+)-3) and (-)-(1S, 5R)-2-oxabicyclo[3.3.1]nonan-3-one ((-)-3). The absolute configuration of product (-)-1 was confirmed by comparison of its optical rotation with the literature data. The absolute configuration the carbon atom hearing hydroxyl group in product (+)-2 was determined using the Mosher's ester. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2009.11.005
• 作为产物：
  描述：

  (S)-3-[bis(ethoxycarbonyl)methyl]cyclohexenone 在 sodium tetrahydroborate 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 以80%的产率得到(-)-diethyl 2-((1S,3S)-3-hydroxycyclohexyl)malonate
  参考文献：
  名称：

  Chemoenzymatic synthesis of 2-oxabicyclo[3.3.1]nonan-3-one enantiomers via microbial reduction by Absidia coerulea AM 93

  摘要：

  Microbial enantioselective reduction of (+/-)-diethyl 2-(3-oxocyclohexyl)malonate (1) has been described. A screening test oil twenty-four fungi strains was carried Out. Most of the microorganisms preferred bioreduction of (+)-isomer of delta-ketoester (1) to (+)-trans delta-hydroxy ester (2) with the anti-Prelog selectivity. Biotransformation conditions using Absidia coerulea AM 93 were optimized with respect to the growth medium, temperature and pH. An effect of 48 chemical additives oil the Course of biotransformation was checked. (-)-Diethyl 2-((S)-3-oxocyclohexyl)malonate ((-)-1) (ee=98%) and (+)-diethyl 2-((1R, 3R)-3-hydroxycyclohexyl)malonate ((+)-2) (ee=99%)were isolated and subjected to chemical lactonization, leading to (+)-(1R, 5S)-2-oxabicyclo[3.3.1]nonan-3-one ((+)-3) and (-)-(1S, 5R)-2-oxabicyclo[3.3.1]nonan-3-one ((-)-3). The absolute configuration of product (-)-1 was confirmed by comparison of its optical rotation with the literature data. The absolute configuration the carbon atom hearing hydroxyl group in product (+)-2 was determined using the Mosher's ester. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2009.11.005