2,2-difluoro-1-hydroxy-3-hexadecanone | 160941-08-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2-difluoro-1-hydroxy-3-hexadecanone
• CAS: 160941-08-2
• 化学式: C₁₆H₃₀F₂O₂
• 分子量: 292.41
• InChiKey: GZGKXHQILKPOHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.88
• 重原子数：
  20.0
• 可旋转键数：
  14.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2,2-difluoro-1-hydroxy-3-hexadecanone 在 N-溴代丁二酰亚胺(NBS) 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 以59%的产率得到1-bromo-2,2-difluoro-3-hexadecanone
  参考文献：
  名称：

  Synthesis and inhibitory activity of difluoroketone substrate analogs of N-myristoyltransferase.

  摘要：

  Two fluorinated nonhydrolyzable analogs of myristoyl-coenzyme A were synthesized and tested for inhibitory activity against N-myristoyltransferase (NMT). S-(2,2-Difluoro-3-oxohexadecyl)-coenzyme A (3) and S-(3,3-difluoro-2-oxopentadecyl)-coenzyme A (2) were prepared by alkylation of coenzyme A and were purified by reverse phase chromatography. Inhibition of NMT was observed with 3 and 2, with IC50's of 110 nM and 80 nM, respectively, in an in vitro assay developed in our laboratory. The known unfluorinated analog S-(2-oxopentadecyl)-coenzyme A (1) was found to have an IC50 of 7 nM. At 100 mu M in D2O, 3 was 59% hydrated and 2 was 88% hydrated.

  DOI：

  10.1016/s0040-4020(01)89601-0
• 作为产物：
  描述：

  聚合甲醛 、 1-chloro-1,1-difluoro-2-pentadecanone 在 四氯化钛 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 6.5h， 以30%的产率得到2,2-difluoro-1-hydroxy-3-hexadecanone
  参考文献：
  名称：

  Synthesis and inhibitory activity of difluoroketone substrate analogs of N-myristoyltransferase.

  摘要：

  Two fluorinated nonhydrolyzable analogs of myristoyl-coenzyme A were synthesized and tested for inhibitory activity against N-myristoyltransferase (NMT). S-(2,2-Difluoro-3-oxohexadecyl)-coenzyme A (3) and S-(3,3-difluoro-2-oxopentadecyl)-coenzyme A (2) were prepared by alkylation of coenzyme A and were purified by reverse phase chromatography. Inhibition of NMT was observed with 3 and 2, with IC50's of 110 nM and 80 nM, respectively, in an in vitro assay developed in our laboratory. The known unfluorinated analog S-(2-oxopentadecyl)-coenzyme A (1) was found to have an IC50 of 7 nM. At 100 mu M in D2O, 3 was 59% hydrated and 2 was 88% hydrated.

  DOI：

  10.1016/s0040-4020(01)89601-0