4,4'-diiodo-1,1'-bibicyclo<2.2.2>octane | 143123-43-7

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机碘化物
• 英文名称: 4,4'-diiodo-1,1'-bibicyclo<2.2.2>octane
• 英文别名: 1-Iodo-4-(4-iodo-1-bicyclo[2.2.2]octanyl)bicyclo[2.2.2]octane
• CAS: 143123-43-7
• 化学式: C₁₆H₂₄I₂
• 分子量: 470.176
• InChiKey: YMMVZFXKJXBMPC-UHFFFAOYSA-N

物化性质

• 沸点：
  414.6±45.0 °C(Predicted)
• 密度：
  1.81±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  4,4'-dimethoxy-1,1'-bibicyclo<2.2.2>octane 在 氢碘酸 作用下， 反应 12.0h， 以95%的产率得到4,4'-diiodo-1,1'-bibicyclo<2.2.2>octane
  参考文献：
  名称：

  The di-.pi.-methane rearrangement. 226. Molecular rods: synthesis and properties

  摘要：

  Our earlier synthetic methodology affording bicyclo[2.2.2]octyl [1]-rod and [2]-rod systems proved inadequate for [41-rods. New synthetic approaches were developed, and [3]- and [41-rod molecules were obtained. Sodium-potassium coupling was employed to afford the longer rod units. A radical anion approach gave lower yields. Hybrid rods with aromatic rings interposed were also synthesized. Rods of 9.2-, 9.7-, 13.4-, 13.9-, and 18.2-angstrom length were included in this study. Consideration of rod chirality suggests each bicyclooctane rod unit to be stereogenic, either P (clockwise) or M (anticlockwise). Thus, in a [1]-rod there are enantiomers and in a [2]-rod there are diastereomers. Molecular mechanics treatment of rod stereoisomerization was carried out. Interconversion of enantiomers of the [l]-rod and diastereomers of the [n]-rods should be very rapid at room temperature. X-ray analysis of the 4,4'-dimethoxy-[2]-rod reveals an achiral conformation. AMI quantum mechanics computations were carried out on [n]-rod radical cations and bridgehead cations.

  DOI：

  10.1021/jo00046a034