1,4-Dimethoxy-bicyclo<2.2.2.>octane | 59880-84-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,4-Dimethoxy-bicyclo<2.2.2.>octane
• 英文别名: 1,4-Dimethoxybicyclo<2.2.2>octane；1,4-Dimethoxybicyclo<2.2.2>octan；Bicyclo(2.2.2)octane, 1,4-dimethoxy-；1,4-dimethoxybicyclo[2.2.2]octane
• CAS: 59880-84-1
• 化学式: C₁₀H₁₈O₂
• 分子量: 170.252
• InChiKey: UJJPXAMWJGOJAC-UHFFFAOYSA-N

物化性质

• 沸点：
  191.9±8.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,4-Dimethoxy-bicyclo<2.2.2.>octane 在 氢碘酸 作用下， 以94%的产率得到1,4-二碘双环[2.2.2]辛烷
  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 silver tetrafluoroborate 、 aluminum tri-bromide 、 碘乙烷 作用下， 反应 5.0h， 生成 1,4-Dimethoxy-bicyclo<2.2.2.>octane
  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

• Brown,R.S., Canadian Journal of Chemistry, 1976, vol. 54, p. 805 - 812
  作者：Brown,R.S.

  DOI：——

  日期：——
• MEIJERE, A. DE;SCHALLNER, O.;GOELITZ, P.;WEBER, W.;SCHLEYER, P. VON, R.;P+, J. ORG. CHEM., 1985, 50, N 25, 5255-5257
  作者：MEIJERE, A. DE、SCHALLNER, O.、GOELITZ, P.、WEBER, W.、SCHLEYER, P. VON, R.、P+

  DOI：——

  日期：——
• 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.