cis-1,2-dihydroxy-3,6-dimethylcyclohexa-3,5-diene | 53501-96-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cis-1,2-dihydroxy-3,6-dimethylcyclohexa-3,5-diene
• 英文别名: (1S,2R)-3,6-dimethylcyclohexa-3,5-diene-1,2-diol
• CAS: 53501-96-5
• 化学式: C₈H₁₂O₂
• 分子量: 140.182
• InChiKey: SYNKFRQUBCHBOW-OCAPTIKFSA-N

物化性质

• 沸点：
  244.9±28.0 °C(Predicted)
• 密度：
  1.139±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  甲醇 、 cis-1,2-dihydroxy-3,6-dimethylcyclohexa-3,5-diene 在 臭氧 、 乙酸丁酯 作用下， 以 phosphate buffer 为溶剂， 反应 8.0h， 生成 2,5-二甲基-4-羟基-3(2H)-呋喃酮
  参考文献：
  名称：

  Directed evolution of the dioxygenase complex for the synthesis of furanone flavor compounds

  摘要：

  Herein we report a new preparation of 4-hydroxy-2,5-dimethyl-2,3 -dihydrofuran-3-one, the flavor compound strawberry furanone, based on a 'green' approach with a minimum number of steps. The first step is an enzymatic dioxygenation of p-xylene to form cyclohexadiene-cis-diol, followed by ring opening via ozonolysis, and ring closure to form the furanone. In efforts to improve the efficiency of the enzymatic step, a directed evolution approach was taken to increase the substrate specificity and selectivity of the toluene dioxygenase enzyme system. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.10.105
• 作为产物：
  描述：

  对二甲苯 在 air 、 E_. coli LS₅₂₁₈ (pTrctodNK₁) expressing toluene dioxygenase 作用下， 生成 cis-1,2-dihydroxy-3,6-dimethylcyclohexa-3,5-diene
  参考文献：
  名称：

  Directed evolution of the dioxygenase complex for the synthesis of furanone flavor compounds

  摘要：

  Herein we report a new preparation of 4-hydroxy-2,5-dimethyl-2,3 -dihydrofuran-3-one, the flavor compound strawberry furanone, based on a 'green' approach with a minimum number of steps. The first step is an enzymatic dioxygenation of p-xylene to form cyclohexadiene-cis-diol, followed by ring opening via ozonolysis, and ring closure to form the furanone. In efforts to improve the efficiency of the enzymatic step, a directed evolution approach was taken to increase the substrate specificity and selectivity of the toluene dioxygenase enzyme system. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.10.105