2-methyl-d3-1-(4,6-dimethyl-s-triazin-2-yl)-1-propanol-3,3,3-d3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: 2-methyl-d3-1-(4,6-dimethyl-s-triazin-2-yl)-1-propanol-3,3,3-d3
• 英文别名: 1,1,1,3,3,3-Hexadeuterio-2-[(4,6-dimethyl-1,3,5-triazin-2-yl)methyl]propan-2-ol
• 化学式: C₉H₁₅N₃O
• 分子量: 187.19
• InChiKey: TWCZURSZFUEBJI-LIJFRPJRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  58.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-methyl-d3-1-(4,6-dimethyl-s-triazin-2-yl)-1-propanol-3,3,3-d3 在 2-甲基苯磺酸 、 乙酸酐 作用下， 以65%的产率得到2,4-dimethyl-6-(2-methyl-d3-1-propenyl-3,3,3-d3)-s-triazine
  参考文献：
  名称：

  Hydration with Mercuric Acetate and the Reduction with 9-BBN−H of 2-(1-Alkenyl)-4,6-dimethyl-s-triazines

  摘要：

  Oxymercuration-demercuration of a double bond in conjugation with the 4,6-dimethyl-s-triazin-2-yl substituent as in alkenes la,b gave anti-Markovnikov regioselectivity, which is explained by the electron-withdrawing nature of the triazinyl substituent. However, hydroboration of the conjugated alkenes with 9-BBN-H gave the corresponding alkanes 5a-c under normal workup conditions with or without oxidation. With time and without workup the hydroboration of 1b gave spectral evidence for the formation of intermediates 9-13 resulting from the migration of the 9-BBN moiety from the a-carbon to a ring nitrogen with concurrent formation of an exocyclic double bond to an a-carbon of the ring. Hydrolysis of the intermediates gave 5a-c. A possible mechanism involving successive allylic rearrangements is presented.

  DOI：

  10.1021/jo010784e
• 作为产物：
  描述：

  2,4,6-三甲基-1,3,5-三嗪 、 氘代丙酮 在 正丁基锂 作用下， 以 乙醚 为溶剂， 反应 0.5h， 以36 mg的产率得到2-methyl-d3-1-(4,6-dimethyl-s-triazin-2-yl)-1-propanol-3,3,3-d3
  参考文献：
  名称：

  Hydration with Mercuric Acetate and the Reduction with 9-BBN−H of 2-(1-Alkenyl)-4,6-dimethyl-s-triazines

  摘要：

  Oxymercuration-demercuration of a double bond in conjugation with the 4,6-dimethyl-s-triazin-2-yl substituent as in alkenes la,b gave anti-Markovnikov regioselectivity, which is explained by the electron-withdrawing nature of the triazinyl substituent. However, hydroboration of the conjugated alkenes with 9-BBN-H gave the corresponding alkanes 5a-c under normal workup conditions with or without oxidation. With time and without workup the hydroboration of 1b gave spectral evidence for the formation of intermediates 9-13 resulting from the migration of the 9-BBN moiety from the a-carbon to a ring nitrogen with concurrent formation of an exocyclic double bond to an a-carbon of the ring. Hydrolysis of the intermediates gave 5a-c. A possible mechanism involving successive allylic rearrangements is presented.

  DOI：

  10.1021/jo010784e