1,1':4',1'':4'',1'''-quaterbicyclo<2.2.2>octane-4,4'''-diyl dioctanoate | 143123-36-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 1,1':4',1'':4'',1'''-quaterbicyclo<2.2.2>octane-4,4'''-diyl dioctanoate
• 英文别名: [4-[4-[4-(4-Octanoyloxy-1-bicyclo[2.2.2]octanyl)-1-bicyclo[2.2.2]octanyl]-1-bicyclo[2.2.2]octanyl]-1-bicyclo[2.2.2]octanyl] octanoate
• CAS: 143123-36-8
• 化学式: C₄₈H₇₈O₄
• 分子量: 719.145
• InChiKey: KGVVLINOLZFVKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.4
• 重原子数：
  52
• 可旋转键数：
  19
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  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

文献信息

• 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.