(S)-4-hydroxy-2-methyl-2-cyclohexen-1-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-4-hydroxy-2-methyl-2-cyclohexen-1-one
• 英文别名: (4S)-4-hydroxy-2-methylcyclohex-2-en-1-one
• 化学式: C₇H₁₀O₂
• 分子量: 126.155
• InChiKey: WFKDLPOPIHXODH-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  6-acetoxy-3-methoxy-2-methyl-2-cyclohexen-1-one 在 lithium aluminium tetrahydride 、 pig liver esterase 、 potassium phosphate buffer 作用下， 以 乙醚 、 二甲基亚砜 为溶剂， 反应 24.0h， 生成 (S)-4-hydroxy-2-methyl-2-cyclohexen-1-one
  参考文献：
  名称：

  A new and efficient chemoenzymatic route to both enantiomers of α′-acetoxy-α-methyl and γ-hydroxy-α-methyl cyclic enones

  摘要：

  A chemoenzymatic synthesis of both enantiomers of the pharmacologically interesting alpha'-acetoxy-alpha-methyl and gamma-hydroxy-alpha-methyl cyclic enones starting from alpha-methyl-beta-methoxy cyclic enones is reported. Manganese(Ill) acetate-mediated acetoxylation followed by the enzyme-mediated hydrolysis of alpha'-acetoxy enone provides acetoxy enones 1a and 2a and hydroxy enones 1b and 2b with high enantiomeric excesses in good yields. The reduction of the acetoxy and hydroxy enones furnished both enantiomers of gamma-hydroxy-alpha-methyl cyclic enones 3 and 4 in a high enantiomeric excess. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.12.006

文献信息

• Enzyme-Catalysed Synthesis of Cyclohex-2-en-1-one<i>cis</i>-Diols from Substituted Phenols, Anilines and Derived 4-Hydroxycyclohex-2-en-1-ones
  作者：Derek R. Boyd、Narain D. Sharma、Peter B. A. McIntyre、Paul J. Stevenson、W. Colin McRoberts、Amit Gohil、Patrick Hoering、Christopher C. R. Allen

  DOI：10.1002/adsc.201700711

  日期：2017.11.23

  phenol bioproduct. Multistep pathways, involving ene reductase- and carbonyl reductase-catalysed reactions, were proposed to account for the production of 4-hydroxycyclohex-2-en-1-one metabolites. Evidence for the phenol hydrate tautomers of 4-hydroxycyclohex-2-en-1-one metabolites was shown by formation of the corresponding trimethylsilyl ether derivatives.

  甲苯双加氧酶催化的顺式取代的苯胺和苯酚基板-dihydroxylations，具有恶臭假单胞菌UV4突变菌株和大肠杆菌的pCL-4T重组菌株，得到相同的芳烃顺-dihydrodiols，其中分离作为优选环己-2-烯1-one顺式-二醇互变异构体。通过对苯胺和苯酚在甲苯双加氧酶活性位点的初步分子对接研究预测了这些顺式-二醇代谢物。使用恶臭假单胞菌对环己-2-烯-1-酮顺式二醇和对苯二酚代谢物进行进一步的生物转化发现UV4全细胞可产生4-羟基环己-2-烯-1-酮作为一种新型的苯酚生物产品。提出了涉及烯还原酶和羰基还原酶催化反应的多步途径，以解释4-羟基环己-2--2--1-酮代谢产物的产生。通过形成相应的三甲基甲硅烷基醚衍生物，显示了4-羟基环己-2-烯-1-酮代谢物的酚水合互变异构体的证据。
• A new and efficient chemoenzymatic route to both enantiomers of α′-acetoxy-α-methyl and γ-hydroxy-α-methyl cyclic enones
  作者：Ayhan S. Demir、Hamide Fındık、Elif Köse

  DOI：10.1016/j.tetasy.2003.12.006

  日期：2004.3

  A chemoenzymatic synthesis of both enantiomers of the pharmacologically interesting alpha'-acetoxy-alpha-methyl and gamma-hydroxy-alpha-methyl cyclic enones starting from alpha-methyl-beta-methoxy cyclic enones is reported. Manganese(Ill) acetate-mediated acetoxylation followed by the enzyme-mediated hydrolysis of alpha'-acetoxy enone provides acetoxy enones 1a and 2a and hydroxy enones 1b and 2b with high enantiomeric excesses in good yields. The reduction of the acetoxy and hydroxy enones furnished both enantiomers of gamma-hydroxy-alpha-methyl cyclic enones 3 and 4 in a high enantiomeric excess. (C) 2003 Elsevier Ltd. All rights reserved.