(-)-(1R,2R)-trans-cyclohexa-3,5-diene-1,2-diol-3-carboxamide | 1237596-87-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (-)-(1R,2R)-trans-cyclohexa-3,5-diene-1,2-diol-3-carboxamide
• CAS: 1237596-87-0
• 化学式: C₇H₉NO₃
• 分子量: 155.153
• InChiKey: HWHPSLMTFLKHPC-PHDIDXHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.31
• 重原子数：
  11.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  83.55
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  rac-(1R,2R)-3-cyanocyclohexa-3,5-diene-1,2-diol 在 水 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 (+)-(1S,2S)-trans-cyclohexa-3,5-diene-1,2-diol-3-carboxamide 、 (-)-(1R,2R)-trans-cyclohexa-3,5-diene-1,2-diol-3-carboxamide 、 5,6-二羟基-1,3-环己二烯-1-羧酸 、 (-)-(1R,2R)-trans-cyclohexa-3,5-diene-1,2-dihydroxy-3-carboxylic acid
  参考文献：
  名称：

  Synthesis of novel cyano-cyclitols and their stereoselective biotransformation catalyzed by Rhodococcus erythropolis A4

  摘要：

  A variety of novel cyano-cyclitols possessing complex stereochemistry have been synthesized. These compounds were subjected to the biocatalyzed hydrolysis of their nitrile groups. The bacterial strain Rhodococcus erythropolis A4, expressing a nitrile hydratase/amidase bienzymatic system, was able to recognize (1R,25,35,4R)/(15,2R,3R,4.5)-1-cyano-2,3,4-trihydroxy-cyclohex-5-ene and trans-3-cyanocyclohexa-3,5-diene-1,2-diol, and to catalyze their transformations into the corresponding amides and acids. The kinetic and stereochemical trends of these biotransformations, a rare example of the enantiorecognition of a rigid bulky aliphatic substrate, are discussed. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.04.022