O,O'-di-(tret-butoxycarbonyl)-2,3-butanediol

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 英文名称: O,O'-di-(tret-butoxycarbonyl)-2,3-butanediol
• 英文别名: Tert-butyl 3-[(2-methylpropan-2-yl)oxycarbonyloxy]butan-2-yl carbonate
• 化学式: C₁₄H₂₆O₆
• 分子量: 290.357
• InChiKey: ZQIYDPMZAGMKPU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  二碳酸二叔丁酯 、 2,3-丁二醇 在 4-二甲氨基吡啶 作用下， 以 乙腈 为溶剂， 反应 0.5h， 生成 起始原料2杂质B 、 O,O'-di-(tret-butoxycarbonyl)-2,3-butanediol
  参考文献：
  名称：

  Di-tert-butyl Dicarbonate and 4-(Dimethylamino)pyridine Revisited. Their Reactions with Amines and Alcohols¹

  摘要：

  The reaction of BOC2O in the presence and absence of DMAP was examined with some amines, alcohols, diols, amino alcohols, and aminothiols. Often, unusual products were observed depending on the ratio of reagents, reaction time, polarity of solvent, pK(a) of alcohols, or type of amine (primary or secondary). In reactions of aliphatic alcohols with BOC2O/DMAP, we isolated for the first time carbonic-carbonic anhydride intermediates; this helps explain the formation of symmetrical carbonates in addition to the O-BOC products. In the case of secondary amines, we succeeded to isolate unstable carbamic-carbonic anhydride intermediates that in the presence of DMAP led to the final N-BOC product. The effect of N-methylimidazole in place of DMAP was also examined.

  DOI：

  10.1021/jo000257f