(2S,4R)-6-heptene-2,4-diyl bis(p-bromobenzoate) | 133850-40-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,4R)-6-heptene-2,4-diyl bis(p-bromobenzoate)
• 英文别名: [(2S,4R)-4-(4-bromobenzoyl)oxyhept-6-en-2-yl] 4-bromobenzoate
• CAS: 133850-40-5
• 化学式: C₂₁H₂₀Br₂O₄
• 分子量: 496.195
• InChiKey: QNACBWIOBXMHGE-IFXJQAMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,4R)-6-heptene-2,4-diyl bis(p-bromobenzoate) 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以96%的产率得到(2S,4R)-2,4-heptanediyl dibenzoate
  参考文献：
  名称：

  A CD method for determination of the absolute stereochemistry of acyclic glycols. 1. Application of the CD exciton chirality method to acyclic 1,3-dibenzoate systems

  摘要：

  To determine the absolute configuration and conformation of chiral acyclic 1,3-glycols, the CD exciton chirality method has been applied to various acyclic 1,3-diesters with p-bromobenzoate, p-chlorobenzoate, or benzoate chromophore. Acyclic anti-1,3-dibenzoates exhibit typical exciton split CD Cotton effects, the sign of which agrees with the sign of the screw sense between two benzoate chromophores in the conformation expanded in a zigzag form. For example, the CD spectrum of bis(p-bromobenzoate) (2S,4S)-2 shows first the positive and then secondly the negative Cotton effects: lambda-ext 252.5 nm, DELTA-epsilon +26.5 and lambda-ext 236.0 nm, DELTA-epsilon -9.1, A = +35.6. On the other hand, syn-1,3-dibenzoates exhibit no exciton split Cotton effects irrespective of the asymmetric structure. Instead the CD spectra of syn-dibenzoates show a weak single Cotton effect: e.g., (2S,4R)-5, lambda-ext 238.0 nm, DELTA-epsilon -1.7. Other 1,3-dibenzoates composed of primary and secondary alcoholic benzoates exhibit exciton split CD Cotton effects of half intensity in comparison with those of anti-1,3-dibenzoates: e.g., 1,3-bis(p-bromobenzoate) (S)-1, lambda-ext 252.6 nm, DELTA-epsilon +13.9 and lambda-ext 235.9 nm, DELTA-epsilon -3.9, A = +17.8. These results provided the CD method for determination of the absolute stereochemistry of acyclic 1,3-glycols.

  DOI：

  10.1021/ja00010a029