4-hydroxy-4'-iodo-1,1'-bibicyclo<2.2.2>octane | 74467-40-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-hydroxy-4'-iodo-1,1'-bibicyclo<2.2.2>octane
• 英文别名: 4'-iodo-1,1'-bi(bicyclo<2.2.2>octan)-4-ol；4'-Iodo-1,1'-bibicyclo<2.2.2>octyl-4-ol；4'-iodo-1,1'-bibicyclo<2.2.2>octan-4-ol；4'-Iodo-1,1'-bibicyclo[2.2.2]octyl-4-ol；4-(4-Iodo-1-bicyclo[2.2.2]octanyl)bicyclo[2.2.2]octan-1-ol
• CAS: 74467-40-6
• 化学式: C₁₆H₂₅IO
• 分子量: 360.278
• InChiKey: UQYINDNPQFZDCD-UHFFFAOYSA-N

物化性质

• 沸点：
  392.3±42.0 °C(Predicted)
• 密度：
  1.52±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  18
• 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：

  4-hydroxy-4'-iodo-1,1'-bibicyclo<2.2.2>octane 在 盐酸 、 K/Na 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.5h， 生成 1,1'-bibicyclo<2.2.2>oct-4-yl acetate
  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 、 silver(I) acetate 、 sodium hydride 、 magnesium 、 碘乙烷 、 nickel dichloride 作用下， 以 乙二醇二甲醚 、 乙醚 、 苯 为溶剂， 反应 20.0h， 生成 4-hydroxy-4'-iodo-1,1'-bibicyclo<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

• Models for photochemical electron transfer at fixed distances. Porphyrin-bicyclo[2.2.2]octane-quinone and porphyrin-bisbicyclo[2.2.2]octane-quinone
  作者：Alvin D. Joran、Burt A. Leland、George G. Geller、John J. Hopfield、Peter B. Dervan

  DOI：10.1021/ja00332a062

  日期：1984.10

  We report the syntheses of three rigidly linked side-by-side porphyrinquinone molecules 2-4 whose edge-to-edge distances are fixed at 6, 10, and 14 A (Figure 1). The spacer units bicyclo[2.2.2]octane and bibicyclo[2.2.2]octane prevent translational displacement and only allow rotational freedom. Our preliminary studies of the fluorescence yields of both the free base PLQ 2a-4a and Zn PLQ 2b-4b systems

  我们报告了三个刚性连接的并排卟啉醌分子 2-4 的合成，其边缘到边缘的距离固定在 6、10 和 14 A（图 1）。间隔单元双环[2.2.2]辛烷和双双环[2.2.2]辛烷防止平移位移，只允许旋转自由。我们对游离碱 PLQ 2a-4a 和 Zn PLQ 2b-4b 系统的荧光产率的初步研究，相对于 1，一种类似的不配备醌的卟啉，揭示了距离依赖性。这表明 2-4 将是研究距离对从激发态卟啉到醌的光化学电子转移的增量影响的有用系统。
• 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.