1-bromo-3,3-difluoro-2-pentadecanone | 160941-14-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-bromo-3,3-difluoro-2-pentadecanone
• 英文别名: 1-bromo-3,3-difluoropentadecan-2-one
• CAS: 160941-14-0
• 化学式: C₁₅H₂₇BrF₂O
• 分子量: 341.28
• InChiKey: ACRHHNSYGFABCT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  19.0
• 可旋转键数：
  13.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  coenzyme A 、 1-bromo-3,3-difluoro-2-pentadecanone 在 sodium carbonate 、 1,4-二巯基-2,3-丁二醇 作用下， 以 水 、 叔丁醇 为溶剂， 反应 6.0h， 以59%的产率得到S-(3,3-difluoro2-oxopentadecyl)-coenzyme A
  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：

  ethyl 2-oxotetradecanoate 在 tetrafluoroboric acid sodium hydroxide 、 草酰氯 、 二乙胺基三氟化硫 、 氢溴酸 作用下， 以 甲醇 、 乙醚 、 氯仿 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 26.5h， 生成 1-bromo-3,3-difluoro-2-pentadecanone
  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