2-hydroxy-2-(spiro[benzo[d][1,3]dioxole-2,1'-cyclohexan]-5-yl)acetonitrile | 134817-19-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 2-hydroxy-2-(spiro[benzo[d][1,3]dioxole-2,1'-cyclohexan]-5-yl)acetonitrile
• CAS: 134817-19-9
• 化学式: C₁₄H₁₅NO₃
• 分子量: 245.278
• InChiKey: BXMXJKJHQFIJBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.68
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  62.48
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  环己酮缩邻苯二酚 在 N-溴代丁二酰亚胺(NBS) 、 溴乙烷 、 acetate buffer 、 magnesium 作用下， 以 乙醚 、 氯仿 为溶剂， 反应 5.0h， 生成 2-hydroxy-2-(spiro[benzo[d][1,3]dioxole-2,1'-cyclohexan]-5-yl)acetonitrile
  参考文献：
  名称：

  Preparation of chiral cyanohydrins by an oxynitrilase-mediated transcyanation

  摘要：

  The transcyanation of aromatic and aliphatic aldehydes 1 (RCHO) with acetone cyanohydrin is catalyzed by the enzyme D-oxynitrilase to afford (R)-cyanohydrins 2 (RCH(OH)CN). The biocatalytic method using acetone cyanohydrin gives products of high enantiomeric purity with better consistency than similar conditions using hydrogen cyanide as the cyanide source. The use of an ether-buffer biphasic solvent system is essential for producing products of optimum optical purity, but the solubility properties of the substrate have a pronounced effect on the enantiomeric purity of the final product. A discussion relating the solubility partition coefficient (log P) of a substrate to the enantiomeric purity of the product as a guide for predicting the outcome with new substrates is presented. Application of the method to the preparation of the following cyanohydrins is reported (R, ee): a, C6H5, 92% ee; b, 3,4-(CH2O2)C6H3, 90% ee; c, 2-(CH3O)C6H4, 96% ee; d, C6H5CH2, 88% ee; e, CH3SCH2CH2, 92% ee; f, CH3(CH2)5CH2, 92% ee; g, (CH3)3C, 92% ee; h, c-C6H11, 96% ee; i, CH3O2C(CH2)6CH2, 97% ee; j, (E,E)-CH3CH = CHCH = CH, 96% ee; k, (CH3)2C = CHCH2CH2C(CH3) = CH, 99% ee.

  DOI：

  10.1021/ja00018a042