1-(4,6-dimethyl-d₆-s-triazin-2-yl)-1,1-d₂-propan-2-ol-d₁ | 138606-47-0

• 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: 1-(4,6-dimethyl-d₆-s-triazin-2-yl)-1,1-d₂-propan-2-ol-d₁
• 英文别名: 2-(1,1-dideuterio-2-deuteriooxypropyl)-4,6-bis(trideuteriomethyl)-1,3,5-triazine
• CAS: 138606-47-0
• 化学式: C₈H₁₃N₃O
• 分子量: 176.139
• InChiKey: VLSUUJSJVHBRQM-VUFJLUSDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.41
• 重原子数：
  12.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  58.9
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-(4,6-dimethyl-d₆-s-triazin-2-yl)-1,1-d₂-propan-2-ol-d₁ 在 2-甲基苯磺酸 、 乙酸酐 、 氘氧化钠 、 重水 作用下， 反应 24.0h， 生成 2,4-dimethyl-d6-6-(1-propenyl-1-d)-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 在 正丁基锂 、 重水 、 氨-d3 作用下， 生成 1-(4,6-dimethyl-d₆-s-triazin-2-yl)-1,1-d₂-propan-2-ol-d₁
  参考文献：
  名称：

  Solvolysis of the sulfonate esters of 1-(4,6-dimethyl-s-triazin-2-yl)-2-propanol and 4-(4,6-dimethyl-s-triazin-2-yl)-2-butanol involving a special salt effect and anchimeric assistance

  摘要：

  The sulfonate esters of 1-(4,6-dimethyl-s-triazin-2-yl)-2-propanol (2a) and of 4-(4,6-dimethyl-s-triazin-2-yl)-2-butanol (3a) have been synthesized and solvolyzed in formic acid and acetic acid to determine their products and rates. The solvolysis of the esters of 2a gave predominantly alkene, and the results of formolysis are consistent with an E2 mechanism. However, in buffered acetic acid the 20-fold increase in rate relative to the unbuffered acetic acid requires the postulation of an E1cB-like mechanism involving ion pairs and a special salt effect by acetate ion. In contrast, the solvolysis of the sulfonate ester of 3a gave a product (11) which resulted from anchimeric assistance by the triazine ring. Qualitative and quantitative evidence of 11 was obtained from the hydrolysis of 11 and subsequent derivatization of the 4-aminopentanoic acid.

  DOI：

  10.1021/jo00031a023