1,1':4',1'':1'''-quaterbicyclo<2.2.2>octane-4,4'''-diol | 143123-35-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,1':4',1'':1'''-quaterbicyclo<2.2.2>octane-4,4'''-diol
• 英文别名: 4-[4-[4-(4-Hydroxy-1-bicyclo[2.2.2]octanyl)-1-bicyclo[2.2.2]octanyl]-1-bicyclo[2.2.2]octanyl]bicyclo[2.2.2]octan-1-ol
• CAS: 143123-35-7
• 化学式: C₃₂H₅₀O₂
• 分子量: 466.748
• InChiKey: ZIQSMYQDFONFKR-UHFFFAOYSA-N

物化性质

• 密度：
  1.279±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  34
• 可旋转键数：
  3
• 环数：
  12.0
• 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

• 作为反应物：
  描述：

  1,1':4',1'':1'''-quaterbicyclo<2.2.2>octane-4,4'''-diol 、 辛酰氯 反应 13.0h， 以85%的产率得到1,1':4',1'':4'',1'''-quaterbicyclo<2.2.2>octane-4,4'''-diyl dioctanoate
  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
• 作为产物：
  描述：

  4-hydroxy-4'-iodo-1,1'-bibicyclo<2.2.2>octane 在 盐酸 、 K/Na 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 9.5h， 生成 1,1':4',1'':1'''-quaterbicyclo<2.2.2>octane-4,4'''-diol
  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