2,5-dideuterio-1-methylimidazole | 87946-04-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2,5-dideuterio-1-methylimidazole
• 英文别名: 2,5-dideutero-1-methylimidazole
• CAS: 87946-04-1
• 化学式: C₄H₆N₂
• 分子量: 84.0892
• InChiKey: MCTWTZJPVLRJOU-NMQOAUCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  6
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,5-dideuterio-1-methylimidazole 、 三甲基硅烷基 2-(氟磺酰基)二氟乙酸酯 在 sodium fluoride 作用下， 以 乙二醇二甲醚 为溶剂， 反应 16.0h， 生成 4-deutero-1-difluoromethyl-3-methyl-1H-imidazol-2-one
  参考文献：
  名称：

  Palladium-Catalyzed Direct Functionalization of Imidazolinone:  Synthesis of Dibromophakellstatin

  摘要：

  The direct C-H functionalization of imidazolinone is achieved with Pd(OAc)(2)/NaOAc in DMSO. Dibromophakellstatin can be synthesized in five steps with 40% overall yield using this new C-H activation method.

  DOI：

  10.1021/ja072844p
• 作为产物：
  描述：

  2,5-二碘-1-甲基-1H-咪唑 在 叔丁基锂 、 重水 作用下， 以 四氢呋喃 、 乙醚 、 正戊烷 为溶剂， 反应 0.08h， 生成 2,5-dideuterio-1-methylimidazole
  参考文献：
  名称：

  Palladium-Catalyzed Direct Functionalization of Imidazolinone:  Synthesis of Dibromophakellstatin

  摘要：

  The direct C-H functionalization of imidazolinone is achieved with Pd(OAc)(2)/NaOAc in DMSO. Dibromophakellstatin can be synthesized in five steps with 40% overall yield using this new C-H activation method.

  DOI：

  10.1021/ja072844p

文献信息

• Carpenter, Andrew J.; Chadwick, Derek J.; Ngochindo Raphael I., Journal of Chemical Research, Miniprint, 1983, # 8, p. 1913 - 1941
  作者：Carpenter, Andrew J.、Chadwick, Derek J.、Ngochindo Raphael I.

  DOI：——

  日期：——
• Phototransposition chemistry of 1-methylpyrazole. Deuterium, methyl, and fluorine substitution
  作者：James W. Pavlik、Edyth M. Kurzweil

  DOI：10.1021/jo00022a019

  日期：1991.10

  1-Methylpyrazole (1) was observed to undergo photo-ring cleavage to 3-(N-methylamino)propenenitrile (17) and phototransposition to 1-methylimidazole (3). Although upon prolonged irradiation 17 is also converted to 3, the efficiency of the 1 --> 17 --> 3 pathway is low and cannot account for a significant fraction of 3 observed upon short-duration irradiation. Under these conditions, deuterium-labeling studies show that 1 phototransposes to 3 by the P4, P6, and P7 permutation patterns in a ratio of 4.8:6.5:1.0. These scrambling patterns are consistent with mechanisms involving ring contration-ring expansion (P4) and electrocyclic ring closure followed by one (P6) or two (P7) sigmatropic shifts of nitrogen. Methyl and fluorine substitution on the 1-methylpyrazole ring reduces reactivity via the P6 and P7 pathways. Thus, 1,5-dimethylpyrazole transposes by these pathways in a ratio of 3.5:1.8:1.0, whereas 5-fluoro-1-methylpyrazole isomerizes only by the P4 and P6 pathways in a ratio of 9.7:1.
• CARPENTER, A. J.;CHADWICK, D. J.;NGOCHINDO, R. I., J. CHEM. RES. MICROFICHE, 1983, N 8, 196-197
  作者：CARPENTER, A. J.、CHADWICK, D. J.、NGOCHINDO, R. I.

  DOI：——

  日期：——