4-Bromo-hex-5-ene-2,3-diol | 184897-23-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-Bromo-hex-5-ene-2,3-diol
• 英文别名: 4-bromohex-5-ene-2,3-diol
• CAS: 184897-23-2
• 化学式: C₆H₁₁BrO₂
• 分子量: 195.056
• InChiKey: KSPKKCBUCDAEDJ-UHFFFAOYSA-N

物化性质

• 沸点：
  288.6±40.0 °C(Predicted)
• 密度：
  1.477±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.68
• 重原子数：
  9.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4-Bromo-hex-5-ene-2,3-diol 在 indium 作用下， 以 水 为溶剂， 反应 7.0h， 生成 (2S,3R)-5-hexene-2,3-diol 、 (2R,3R)-Hex-5-ene-2,3-diol
  参考文献：
  名称：

  Comparative Diastereoselectivity Analysis of Crotylindium and 3-Bromoallylindium Additions to α-Oxy Aldehydes in Aqueous and Nonaqueous Solvent Systems

  摘要：

  The couplings of crotyl bromide (1) and 1,3-dibromopropene (2) to a triad of conformationally unrestricted a-oxy aldehydes in water, aqueous THF (1:1), and anhydrous THF are described. In no example involving 1 was the formation of anti,syn product detected. The proportion of syn isomers reached a maximum (syn/anti = 5.6:1) when the neighboring hydroxyl group was unprotected and water was the reaction medium. Although internal chelation also operates to some degree with 2, considerable erosion of this mechanistic pathway (maximum now only 2:1) in favor of Felkin and ''anti-Felkin'' transition states is reflected in the product distributions. This trend can be synthetically advantageous, and a utilitarian example is demonstrated. The indium reagents studied here are notably efficient nucleophilic reaction partners in water.

  DOI：

  10.1021/jo9613489
• 作为产物：
  描述：

  trans 1,3-dibromoprop-1-ene 、 2-hydroxypropanal 以 水 为溶剂， 反应 4.0h， 以80%的产率得到4-Bromo-hex-5-ene-2,3-diol
  参考文献：
  名称：

  Comparative Diastereoselectivity Analysis of Crotylindium and 3-Bromoallylindium Additions to α-Oxy Aldehydes in Aqueous and Nonaqueous Solvent Systems

  摘要：

  The couplings of crotyl bromide (1) and 1,3-dibromopropene (2) to a triad of conformationally unrestricted a-oxy aldehydes in water, aqueous THF (1:1), and anhydrous THF are described. In no example involving 1 was the formation of anti,syn product detected. The proportion of syn isomers reached a maximum (syn/anti = 5.6:1) when the neighboring hydroxyl group was unprotected and water was the reaction medium. Although internal chelation also operates to some degree with 2, considerable erosion of this mechanistic pathway (maximum now only 2:1) in favor of Felkin and ''anti-Felkin'' transition states is reflected in the product distributions. This trend can be synthetically advantageous, and a utilitarian example is demonstrated. The indium reagents studied here are notably efficient nucleophilic reaction partners in water.

  DOI：

  10.1021/jo9613489