O,O'-di-(tert-butoxycarbonyl)ethanediol

• 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-(tert-butoxycarbonyl)ethanediol
• 英文别名: Tert-butyl 2-[(2-methylpropan-2-yl)oxycarbonyloxy]ethyl carbonate；tert-butyl 2-[(2-methylpropan-2-yl)oxycarbonyloxy]ethyl carbonate
• 化学式: C₁₂H₂₂O₆
• 分子量: 262.303
• InChiKey: VGRYJYZAROFZTJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 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 、 乙二醇 在 4-二甲氨基吡啶 作用下， 以 乙腈 为溶剂， 反应 0.5h， 生成 碳酸乙烯酯 、 O,O'-di-(tert-butoxycarbonyl)ethanediol
  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

文献信息

• A New, Efficient, and Catalyst-free Microwave-assisted Approach for Formation of <i>O</i>-<i>tert</i>-Butoxy Carbonates
  作者：Hacène K’tir、Aïcha Amira、Malika Berredjem、Nour-Eddine Aouf

  DOI：10.1246/cl.140075

  日期：2014.6.5

  A new simple, efficient, greener, and catalyst-free chemoselective protocol for the O-tert-butoxycarbonylation of various structurally diverse hydroxy compounds was carried out with (Boc)2O under microwave radiation. The corresponding O-tert-butoxy carbonates were obtained in good to excellent yields in a short reaction time without any side reactions.

  一种新的简单、高效、绿色且无催化剂的化学选择性方案用于各种结构多样的羟基化合物的O-叔丁氧基碳酰化，反应使用了（Boc）2O，并在微波辐射下进行。相应的O-叔丁氧基碳酸酯在较短的反应时间内以良好到优秀的产率获得，且没有任何副反应。
• METHOD FOR PRODUCING TETRAFLUORO COMPOUND
  申请人：Miyashita Yasuhiro

  公开号：US20110178323A1

  公开（公告）日：2011-07-21

  Provided is a method for producing a tetrafluoro nitrogen-containing heterocyclic compound such as tetrafluoropyrrolidine in good yield and at low cost. The method comprises the steps of: (A) reacting a compound represented by the formula (I) with fluorine gas to produce a tetrafluoro compound represented by the formula (II), (B) converting the tetrafluoro derivative represented by the formula (II) to a compound represented by the formula (III), and (C) reacting the compound represented by the formula (III) with an amine compound represented by the formula NH 2 R 9 to produce a tetrafluoro nitrogen-containing heterocyclic compound represented by the formula (IV) or salt thereof.

  提供了一种生产四氟氮含杂环化合物（如四氟吡咯烷）的方法，产率高且成本低。该方法包括以下步骤：（A）将式（I）表示的化合物与氟气反应，生成式（II）表示的四氟化合物，（B）将式（II）表示的四氟衍生物转化为式（III）表示的化合物，以及（C）将式（III）表示的化合物与式NH2R9表示的胺化合物反应，生成式（IV）表示的四氟氮含杂环化合物或其盐。