(+)-2-fluoro-4,4-diphenylcyclohexanone | 1266339-04-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (+)-2-fluoro-4,4-diphenylcyclohexanone
• 英文别名: (2R)-2-fluoro-4,4-diphenylcyclohexan-1-one
• CAS: 1266339-04-1
• 化学式: C₁₈H₁₇FO
• 分子量: 268.331
• InChiKey: LZKGZCFBYPRVQG-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4,4-二苯基环己酮 在 (9R)-10,11-二氢-6'-甲氧基奎宁-9-胺三盐酸盐 、 水 、 sodium carbonate 、 N-氟代双苯磺酰胺 、 三氯乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以87%的产率得到(+)-2-fluoro-4,4-diphenylcyclohexanone
  参考文献：
  名称：

  Enantioselective Organocatalytic α-Fluorination of Cyclic Ketones

  摘要：

  The first highly enantioselective alpha-fluorination of ketones using organocatalysis has been accomplished. The long-standing problem of enantioselective ketone alpha-fluorination via enamine activation has been overcome via high-throughput evaluation of a new library of amine catalysts. The optimal system, a primary amine functionalized Cinchona alkaloid, allows the direct and asymmetric a-fluorination of a variety of carbo- and heterocyclic substrates. Furthermore, this protocol also provides diastereo-, regio-, and chemoselective catalyst control in fluorinations involving complex carbonyl systems.

  DOI：

  10.1021/ja111163u

文献信息

• Enantioselective Organocatalytic α-Fluorination of Cyclic Ketones
  作者：Piotr Kwiatkowski、Teresa D. Beeson、Jay C. Conrad、David W. C. MacMillan

  DOI：10.1021/ja111163u

  日期：2011.2.16

  The first highly enantioselective alpha-fluorination of ketones using organocatalysis has been accomplished. The long-standing problem of enantioselective ketone alpha-fluorination via enamine activation has been overcome via high-throughput evaluation of a new library of amine catalysts. The optimal system, a primary amine functionalized Cinchona alkaloid, allows the direct and asymmetric a-fluorination of a variety of carbo- and heterocyclic substrates. Furthermore, this protocol also provides diastereo-, regio-, and chemoselective catalyst control in fluorinations involving complex carbonyl systems.