(3S,4R,5S,6R)-1,1-dibromo-octa-1,7-diene-3,4,5,6-tetrol | 697756-56-2

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代醇
• 英文名称: (3S,4R,5S,6R)-1,1-dibromo-octa-1,7-diene-3,4,5,6-tetrol
• CAS: 697756-56-2
• 化学式: C₈H₁₂Br₂O₄
• 分子量: 331.989
• InChiKey: HYXUZBPFAZAJPQ-HETMPLHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.25
• 重原子数：
  14.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  80.92
• 氢给体数：
  4.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (3S,4R,5S,6R)-1,1-dibromo-octa-1,7-diene-3,4,5,6-tetrol 在 吡啶 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 12.0h， 生成 (3S,4R,5S,6R)-3,4,5,6-tetra-O-acetyl-oct-7-en-1-yne-3,4,5,6-tetrol
  参考文献：
  名称：

  An Efficient Way to 1,7-Enynes and Ethyl 8-Yn-2-enoates from Aldohexoses and to Polyhydroxylated 1-Vinylcyclohexenes

  摘要：

  In this paper, we report the synthesis of carbohydrate-derived 1,7-enynes and subsequent metathesis to yield polyhydroxylated 1-vinylcyclohexenes. For example, we converted D-glucose 2 to the (6,7)dideoxy-D-gluco-hept-6-ene-pyranose 7, which led to the desired 1,7-enyne 16. The ring-closing metathesis of this 1,7-enyne 16 with the second generation Grubbs catalyst, under Mori's conditions, gave the corresponding polyhydroxylated 1-vinylcyclohexene 25 in 76% yield. The conversion of several aldohexoses into polyhydroxylated 1-vinylcyclohexenes was carried out with satisfying yields. We report also the synthesis of two carbohydrate-derived ethyl 8-yn-2-enoates from D-glucose derivatives.

  DOI：

  10.1021/jo035437e
• 作为产物：
  描述：

  6,7-dideoxy-α,β-D-galacto-hept-6-enopyranose 、 (dibromomethyl)(triphenyl)phosphonium bromide 在 锌 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.5h， 以70%的产率得到(3S,4R,5S,6R)-1,1-dibromo-octa-1,7-diene-3,4,5,6-tetrol
  参考文献：
  名称：

  An Efficient Way to 1,7-Enynes and Ethyl 8-Yn-2-enoates from Aldohexoses and to Polyhydroxylated 1-Vinylcyclohexenes

  摘要：

  In this paper, we report the synthesis of carbohydrate-derived 1,7-enynes and subsequent metathesis to yield polyhydroxylated 1-vinylcyclohexenes. For example, we converted D-glucose 2 to the (6,7)dideoxy-D-gluco-hept-6-ene-pyranose 7, which led to the desired 1,7-enyne 16. The ring-closing metathesis of this 1,7-enyne 16 with the second generation Grubbs catalyst, under Mori's conditions, gave the corresponding polyhydroxylated 1-vinylcyclohexene 25 in 76% yield. The conversion of several aldohexoses into polyhydroxylated 1-vinylcyclohexenes was carried out with satisfying yields. We report also the synthesis of two carbohydrate-derived ethyl 8-yn-2-enoates from D-glucose derivatives.

  DOI：

  10.1021/jo035437e