1-methyl-5-[{2'-(tert-butyldimethylsilyloxy)phenyl}hydroxymethyl]-4-fluoro-1H-pyrazole | 1033700-97-8

• 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: 1-methyl-5-[{2'-(tert-butyldimethylsilyloxy)phenyl}hydroxymethyl]-4-fluoro-1H-pyrazole
• 英文别名: [2-[Tert-butyl(dimethyl)silyl]oxyphenyl]-(4-fluoro-2-methylpyrazol-3-yl)methanol
• CAS: 1033700-97-8
• 化学式: C₁₇H₂₅FN₂O₂Si
• 分子量: 336.482
• InChiKey: AVLVYXADJOPBGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.02
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  47.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-methyl-5-[{2'-(tert-butyldimethylsilyloxy)phenyl}hydroxymethyl]-4-fluoro-1H-pyrazole 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以89%的产率得到1-methyl-5-[2'-(tert-butyldimethylsilyloxy)benzoyl]-4-fluoro-1H-pyrazole
  参考文献：
  名称：

  Reaction of N-Methyl-5-tributylstannyl-4-fluoro-1H-pyrazole and Its Application to N-Methyl-chromeno[2,3-d]pyrazol-9-one Synthesis

  摘要：

  N-Methylation by sequential treatment of 5-tributylstannyl-4-fluoro-1H-pyrazole 1 with LDA and iodomethane regioselectively afforded the compound 2a in high yield. The addition reaction of 5-lithiated-4-fluoro-1H-pyrazole generated from 2a with a wide range of electrophiles allowed a facile introduction of different substituents at position 5 in good yields. The adduct 3d was efficiently converted to N-methyl-chromeno[2,3-d]pyrazol-9-one 9 in 3 steps.

  DOI：

  10.1021/jo800431t
• 作为产物：
  描述：

  1-methyl-5-tributylstannyl-4-fluoro-1H-pyrazole 、 2-((tert-butyldimethylsilyl)oxy)benzaldehyde 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以94%的产率得到1-methyl-5-[{2'-(tert-butyldimethylsilyloxy)phenyl}hydroxymethyl]-4-fluoro-1H-pyrazole
  参考文献：
  名称：

  Reaction of N-Methyl-5-tributylstannyl-4-fluoro-1H-pyrazole and Its Application to N-Methyl-chromeno[2,3-d]pyrazol-9-one Synthesis

  摘要：

  N-Methylation by sequential treatment of 5-tributylstannyl-4-fluoro-1H-pyrazole 1 with LDA and iodomethane regioselectively afforded the compound 2a in high yield. The addition reaction of 5-lithiated-4-fluoro-1H-pyrazole generated from 2a with a wide range of electrophiles allowed a facile introduction of different substituents at position 5 in good yields. The adduct 3d was efficiently converted to N-methyl-chromeno[2,3-d]pyrazol-9-one 9 in 3 steps.

  DOI：

  10.1021/jo800431t

文献信息

• Reaction of <i>N</i>-Methyl-5-tributylstannyl-4-fluoro-1<i>H</i>-pyrazole and Its Application to <i>N</i>-Methyl-chromeno[2,3-<i>d</i>]pyrazol-9-one Synthesis
  作者：Takeshi Hanamoto、Eri Hashimoto、Masayuki Miura、Hiroshi Furuno、Junji Inanaga

  DOI：10.1021/jo800431t

  日期：2008.6.1

  N-Methylation by sequential treatment of 5-tributylstannyl-4-fluoro-1H-pyrazole 1 with LDA and iodomethane regioselectively afforded the compound 2a in high yield. The addition reaction of 5-lithiated-4-fluoro-1H-pyrazole generated from 2a with a wide range of electrophiles allowed a facile introduction of different substituents at position 5 in good yields. The adduct 3d was efficiently converted to N-methyl-chromeno[2,3-d]pyrazol-9-one 9 in 3 steps.