1,1'-Bibicyclo<2.2.2>octyl-4-ol | 74467-48-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,1'-Bibicyclo<2.2.2>octyl-4-ol
• 英文别名: 1,1'-bibicyclo<2.2.2>octan-4-ol；1,1'-Bibicyclo[2.2.2]octyl-4-ol；4-(1-Bicyclo[2.2.2]octanyl)bicyclo[2.2.2]octan-1-ol
• CAS: 74467-48-4
• 化学式: C₁₆H₂₆O
• 分子量: 234.382
• InChiKey: VDOKJPBVYZJRMT-UHFFFAOYSA-N

物化性质

• 沸点：
  337.5±10.0 °C(Predicted)
• 密度：
  1.167±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  17
• 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：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,1'-Bibicyclo<2.2.2>octyl-4-ol 在 硫酸 作用下， 以 四氯乙烯 为溶剂， 反应 20.0h， 生成 1,4-bis(1,1'-bibicyclo<2.2.2>oct-4-yl)benzene
  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：

  1,4-二氯双环[2.2.2]辛烷 在 氢氧化钾 、 aluminum tri-bromide 、 氢碘酸 、 叔丁基锂 、 silver(I) acetate 、 sodium hydride 、 magnesium 、 碘乙烷 、 nickel dichloride 作用下， 以 乙二醇二甲醚 、 乙醚 、 正戊烷 、 苯 为溶剂， 反应 21.0h， 生成 1,1'-Bibicyclo<2.2.2>octyl-4-ol
  参考文献：
  名称：

  Rod-like organic molecules. Energy-transfer studies using single-photon counting

  摘要：

  DOI：

  10.1021/jo01308a001

文献信息

• Rod-like organic molecules. Energy-transfer studies using single-photon counting
  作者：Howard E. Zimmerman、Theodore D. Goldman、Timothy K. Hirzel、Steven P. Schmidt

  DOI：10.1021/jo01308a001

  日期：1980.9
• The di-.pi.-methane rearrangement. 226. Molecular rods: synthesis and properties
  作者：Howard E. Zimmerman、Russell K. King、Michael B. Meinhardt

  DOI：10.1021/jo00046a034

  日期：1992.9

  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.