4-methoxy-4''-(1,3,6,9-tetraoxaundecyl)-1,1':4',1''-terbicyclo<2.2.2>octane | 143123-41-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methoxy-4''-(1,3,6,9-tetraoxaundecyl)-1,1':4',1''-terbicyclo<2.2.2>octane
• 英文别名: 1-[2-(2-Ethoxyethoxy)ethoxymethoxy]-4-[4-(4-methoxy-1-bicyclo[2.2.2]octanyl)-1-bicyclo[2.2.2]octanyl]bicyclo[2.2.2]octane
• CAS: 143123-41-5
• 化学式: C₃₂H₅₄O₅
• 分子量: 518.778
• InChiKey: WYTFNZBMJTWOEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  37
• 可旋转键数：
  13
• 环数：
  9.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-methoxy-4''-(1,3,6,9-tetraoxaundecyl)-1,1':4',1''-terbicyclo<2.2.2>octane 在 盐酸 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 生成 4''-methoxy-1,1':4',1''-terbicyclo<2.2.2>octane-1-ol
  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 K/Na 、 N,N-二异丙基乙胺 作用下， 以 乙二醇二甲醚 、 二氯甲烷 为溶剂， 反应 9.0h， 生成 4-methoxy-4''-(1,3,6,9-tetraoxaundecyl)-1,1':4',1''-terbicyclo<2.2.2>octane
  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.