1,1'-bibicyclo<2.2.2>octane-4,4'-diyl diacetate | 116278-39-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,1'-bibicyclo<2.2.2>octane-4,4'-diyl diacetate
• 英文别名: 4,4'-diacetoxy-1,1'-bibicyclo<2.2.2>octane；4,4'-diacetoxy-1,1'-bibicyclo[2.2.2]octane；[4-(4-acetyloxy-1-bicyclo[2.2.2]octanyl)-1-bicyclo[2.2.2]octanyl] acetate
• CAS: 116278-39-8
• 化学式: C₂₀H₃₀O₄
• 分子量: 334.456
• InChiKey: MZRKDGDNPQUAIA-UHFFFAOYSA-N

物化性质

• 沸点：
  394.8±42.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1,1'-bibicyclo<2.2.2>octane-4,4'-diyl diacetate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以90%的产率得到4,4'-dihydroxy-1,1'-bibicyclo<2.2.2>octane
  参考文献：
  名称：

  Transmission of polar substituent effects through the bicyclo[2.2.2]octane ring system as monitored by fluorine-19 NMR shifts: 19F NMR study of 10-substituted 9-fluorotriptycenes and 4-substituted-4'-fluorobibicyclo[2.2.2]octanes

  摘要：

  DOI：

  10.1021/jo00257a011
• 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 3.0h， 生成 1,1'-bibicyclo<2.2.2>octane-4,4'-diyl diacetate
  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