(2S^*,3S^*)-(+/-)-1,4-dibromo-2,3-dimethylbutane-2,3-diol | 20955-40-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S^*,3S^*)-(+/-)-1,4-dibromo-2,3-dimethylbutane-2,3-diol
• 英文别名: (2RS,3RS)-1,4-dibromo-2,3-dimethylbutane-2,3-diol；(2S,3S)-1,4-dibromo-2,3-dimethylbutane-2,3-diol
• CAS: 20955-40-2；142483-93-0
• 化学式: C₆H₁₂Br₂O₂
• 分子量: 275.968
• InChiKey: KTECVKAQDIEHPU-PHDIDXHHSA-N

物化性质

• 熔点：
  93 °C
• 沸点：
  148 °C(Press: 16 Torr)
• 密度：
  1.851±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (3R,4R)-3,4-bis(bromomethyl)-3,4-dimethyldioxetane 在 glutathione 作用下， 以 水 为溶剂， 反应 8.0h， 以43%的产率得到(2S^*,3S^*)-(+/-)-1,4-dibromo-2,3-dimethylbutane-2,3-diol
  参考文献：
  名称：

  Electron versus hydride ion transfer in the reduction of .beta.-halogen-substituted 1,2-dioxetanes by 1,4-dihydronicotinamides

  摘要：

  The 3-halo-substituted 1,2-dioxetane 1 was employed as mechanistic probe in the reaction with NADH model compounds, namely, three N-substituted 1,4-dihydronicotinamides and 9,10-dihydro-10-methylacridine (AcrH-2), to differentiate between the direct hydride ion transfer and the electron transfer (SET) mechanisms. While AcrH-2 led mostly to cleavage into carbonyl products, the nicotinamides reduced the dioxetane 1 to yield the epoxy alcohol 3 as the main product. Additionally, the diol 2, the cleavage product bromoacetone, and the dehalogenation product acetone were observed. The formation of 3 is interpreted in terms of direct hydride ion transfer from the nicotinamides to the dioxetane with subsequent bromide elimination of the intermediary alkoxide. The dehalogenation product acetone was taken as evidence for initial electron transfer.

  DOI：

  10.1021/jo00042a033

文献信息

• The Reaction of 1,2:3,4-Diepoxy-2,3-dimethylbutane with Nucleophiles
  作者：Frédéric Farkas、Thomas Wellauer、Thomas Esser、Urs Séquin

  DOI：10.1002/hlca.19910740715

  日期：1991.10.30

  To find out whether the 1,4-addition to 1,2:3,4-diepoxides, which so far has been observed only once, is of a more general character, we investigated the reaction of a variety of O-, C-, N-, and S-nucleophiles with the model compound 1,2:3,4-diepoxy-2,3-dimethylbutane (Scheme 4). In several cases, 1,4-addition products could, indeed, be observed besides the expected 1,2-adducts (Table).

  为了找出到目前为止仅观察到一次的1,2：3,4-二环氧化合物的1,4-加成是否具有更一般的特征，我们研究了各种O-，C-的反应，N-和S-亲核试剂与模型化合物1,2：3,4-二环氧-2,3-二甲基丁烷（方案4）。在某些情况下，除预期的1,2-加合物外，实际上还可以观察到1,4-加成产物（表）。