(-)-3-trifluoromethanesulfonyloxy-10-keto-N-methylmorphinan | 496848-59-0

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 吗啡烷
• 英文名称: (-)-3-trifluoromethanesulfonyloxy-10-keto-N-methylmorphinan
• 英文别名: Morphinan-10-one, 17-methyl-3-[[(trifluoromethyl)sulfonyl]oxy]-；[(1R,9S,10R)-17-methyl-8-oxo-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-trien-4-yl] trifluoromethanesulfonate
• CAS: 496848-59-0
• 化学式: C₁₈H₂₀F₃NO₄S
• 分子量: 403.422
• InChiKey: UKXVTUMRGSOECX-JLJPHGGASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.24
• 重原子数：
  27.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  63.68
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  氰化锌 、 (-)-3-trifluoromethanesulfonyloxy-10-keto-N-methylmorphinan 在 四(三苯基膦)钯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 以89.5%的产率得到(-)-3-cyano-3-desoxy-10-keto-N-methylmorphinan
  参考文献：
  名称：

  Microwave-Promoted Pd-Catalyzed Cyanation of Aryl Triflates:  A Fast and Versatile Access to 3-Cyano-3-desoxy-10-ketomorphinans

  摘要：

  [GRAPHICS]A methodology for the microwave-promoted conversion of triflates to the corresponding nitriles by using 8% equiv of Pd(Ph3P)(4) as the catalyst and 2.0 equiv of Zn(CN)(2) as the cyanide source has been developed. This method is highly efficient for the preparation of 3-cyano-3-desoxy10-ketomorphinans. The reaction was generally completed in 15 min at 200 degreesC and produced products in greater than 86% yields.

  DOI：

  10.1021/ol027256p
• 作为产物：
  描述：

  N-苯基双(三氟甲烷磺酰)亚胺 、 MCL 172 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以70%的产率得到(-)-3-trifluoromethanesulfonyloxy-10-keto-N-methylmorphinan
  参考文献：
  名称：

  Microwave-Promoted Pd-Catalyzed Cyanation of Aryl Triflates:  A Fast and Versatile Access to 3-Cyano-3-desoxy-10-ketomorphinans

  摘要：

  [GRAPHICS]A methodology for the microwave-promoted conversion of triflates to the corresponding nitriles by using 8% equiv of Pd(Ph3P)(4) as the catalyst and 2.0 equiv of Zn(CN)(2) as the cyanide source has been developed. This method is highly efficient for the preparation of 3-cyano-3-desoxy10-ketomorphinans. The reaction was generally completed in 15 min at 200 degreesC and produced products in greater than 86% yields.

  DOI：

  10.1021/ol027256p