3-[(1S,2R)-2-hydroxy-1-methyl-6-oxocyclohexyl]propanenitrile | 109214-44-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-[(1S,2R)-2-hydroxy-1-methyl-6-oxocyclohexyl]propanenitrile
• CAS: 109214-44-0
• 化学式: C₁₀H₁₅NO₂
• 分子量: 181.235
• InChiKey: AVOVKZFBZDOLRH-SCZZXKLOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  61.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-甲基-1,3-环己二酮 在 sodium tetrahydroborate 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 19.0h， 生成 3-[(1S,2R)-2-hydroxy-1-methyl-6-oxocyclohexyl]propanenitrile
  参考文献：
  名称：

  Asymmetric microbial reduction of prochiral 2,2,-disubstituted cycloalkanediones

  摘要：

  DOI：

  10.1021/jo00391a009

文献信息

• Comparative reductive desymmetrization of 2,2-disubstituted-cycloalkane-1,3-diones
  作者：Jeremy M. Carr、Timothy S. Snowden

  DOI：10.1016/j.tet.2008.01.065

  日期：2008.3

  Reductive desymmetrization of 2-methyl-2-substituted-cycloalkane-1,3-diones can be effected using either NaBH(4) in DME or lithium tri-tert-butoxyaluminum hydride (LTBA) in THF at -60 degrees C. The former is a new approach that offers slightly greater diastereoselectivity in the reduction of 2,2-disubstituted-cyclopentane- 1,3-diones while LTBA is superior with 2,2-disubstituted-cyclohexane- 1,3-diones. Both conditions minimize subsequent reduction to diols thereby furnishing high yields of 1,3-ketols. Particularly rapid monoreductions are observed with 2-methyl-2-nitroethylcyclopentane-1,3-dione and 2-cyanoethyl-2-methylcyclopentane-1,3-dione when treated with NaBH(4) in DME at -60 degrees C. As expected, diastereoselectivity varies considerably with the substitution at C-2. (C) 2008 Elsevier Ltd. All rights reserved.