decakis(bromomethyl)biphenyl | 132590-72-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: decakis(bromomethyl)biphenyl
• 英文别名: 1,2,3,4,5-Pentakis(bromomethyl)-6-[2,3,4,5,6-pentakis(bromomethyl)phenyl]benzene；1,2,3,4,5-pentakis(bromomethyl)-6-[2,3,4,5,6-pentakis(bromomethyl)phenyl]benzene
• CAS: 132590-72-8
• 化学式: C₂₂H₂₀Br₁₀
• 分子量: 1083.44
• InChiKey: SAYJCOIRCGQNHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  Decamethylbiphenyl 在 四丁基溴化铵 溴 作用下， 以 四氯化碳 为溶剂， 反应 48.0h， 以69%的产率得到decakis(bromomethyl)biphenyl
  参考文献：
  名称：

  Conformational shift by mutual steric interactions between two multiarmed units

  摘要：

  Decakis(bromomethyl)biphenyl (3) has been prepared by reaction of decamethylbiphenyl with Br2/CCl4 in the presence of tetrabutylammonium bromide as catalyst. The attempted synthesis of decakis(bromomethyl)benzophenone resulted only in bromopentakis(bromomethyl)benzene (8). X-ray diffraction of a single crystal of 3 shows that the preferred conformation of 3 is not the alternate ''up-down'' conformation observed for the parent hexakis(bromomethyl)benzene, but a conformation in which the up-down alternation of the CH2Br groups is disrupted at the meta-para position of each ring. MM(85) calculations on 3 indicate that some conformations with disrupted ''up-down'' alternation of the CH2Br groups are favored over the all-alternate up-down form. It is suggested that this conformational shift is the result of the mutual steric interactions between arms of different moieties, and that syn interactions between m- and p-CH2Br groups operate in order to avoid bromine contacts between ortho groups at different rings. The barrier for Ar-CH2Br rotation was estimated from dynamic NMR data as 12.5 kcal mol-1.

  DOI：

  10.1021/jo00007a035

文献信息

• Conformational shift by mutual steric interactions between two multiarmed units
  作者：Naama Zuaretz、Oren Golan、Silvio Biali

  DOI：10.1021/jo00007a035

  日期：1991.3

  Decakis(bromomethyl)biphenyl (3) has been prepared by reaction of decamethylbiphenyl with Br2/CCl4 in the presence of tetrabutylammonium bromide as catalyst. The attempted synthesis of decakis(bromomethyl)benzophenone resulted only in bromopentakis(bromomethyl)benzene (8). X-ray diffraction of a single crystal of 3 shows that the preferred conformation of 3 is not the alternate ''up-down'' conformation observed for the parent hexakis(bromomethyl)benzene, but a conformation in which the up-down alternation of the CH2Br groups is disrupted at the meta-para position of each ring. MM(85) calculations on 3 indicate that some conformations with disrupted ''up-down'' alternation of the CH2Br groups are favored over the all-alternate up-down form. It is suggested that this conformational shift is the result of the mutual steric interactions between arms of different moieties, and that syn interactions between m- and p-CH2Br groups operate in order to avoid bromine contacts between ortho groups at different rings. The barrier for Ar-CH2Br rotation was estimated from dynamic NMR data as 12.5 kcal mol-1.