Heptachloro-7-(trifluoromethyl)naphthalene

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Heptachloro-7-(trifluoromethyl)naphthalene
• 英文别名: 1,2,3,4,5,6,8-Heptachloro-7-(trifluoromethyl)naphthalene
• 化学式: C₁₁Cl₇F₃
• 分子量: 437.287
• InChiKey: KSQWOWJBDJHZNH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Heptachloro-7-(trifluoromethyl)naphthalene 在 三氯化铝 作用下， 以 二硫化碳 为溶剂， 反应 3.0h， 以70%的产率得到Perchloro-2-methylnaphthalene
  参考文献：
  名称：

  Perchloro-2-methylnaphthalene, a Novel Chlorocarbon with a Highly Strained Structure

  摘要：

  Perchloro-2-methylnaphthalene (1) is prepared in a two-step reaction: treatment of 2H-heptachloronaphthalene (3) with CCl3F in the presence of AlCl3 yields heptachloro-7-(trifluoromethyl)naphthalene (4), which in CS2 and with an excess of AlCl3 affords 1. The spectra and X-ray crystal structure of chlorocarbon 1 are reported, as well as that of the much less strained heptachloro-7-(dichloromethyl)naphthalene (10). The unusual UV spectrum, due to the distortion of the aromatic rings, is also discussed. The reduction of 1 with copper wire to give perchloro(2-naphthyl)methyl radical (11) has been studied by means of electron spin resonance. Steric inhibition to resonance of the free electron within the aromatic ring in 11 has been estimated by a semiempirical AM1 method.

  DOI：

  10.1021/jo00114a019
• 作为产物：
  描述：

  一氟三氯甲烷 、 1,2,3,4,5,6,8-heptachloronaphthalene 在 三氯化铝 作用下， 反应 9.5h， 以83%的产率得到Heptachloro-7-(trifluoromethyl)naphthalene
  参考文献：
  名称：

  Perchloro-2-methylnaphthalene, a Novel Chlorocarbon with a Highly Strained Structure

  摘要：

  Perchloro-2-methylnaphthalene (1) is prepared in a two-step reaction: treatment of 2H-heptachloronaphthalene (3) with CCl3F in the presence of AlCl3 yields heptachloro-7-(trifluoromethyl)naphthalene (4), which in CS2 and with an excess of AlCl3 affords 1. The spectra and X-ray crystal structure of chlorocarbon 1 are reported, as well as that of the much less strained heptachloro-7-(dichloromethyl)naphthalene (10). The unusual UV spectrum, due to the distortion of the aromatic rings, is also discussed. The reduction of 1 with copper wire to give perchloro(2-naphthyl)methyl radical (11) has been studied by means of electron spin resonance. Steric inhibition to resonance of the free electron within the aromatic ring in 11 has been estimated by a semiempirical AM1 method.

  DOI：

  10.1021/jo00114a019

文献信息

• Perchloro-2-methylnaphthalene, a Novel Chlorocarbon with a Highly Strained Structure
  作者：J. Carilla、Ll. Fajari、R. Garcia、L. Julia、C. Marcos、J. Riera、C. R. Whitaker、J. Rius、C. Aleman

  DOI：10.1021/jo00114a019

  日期：1995.5

  Perchloro-2-methylnaphthalene (1) is prepared in a two-step reaction: treatment of 2H-heptachloronaphthalene (3) with CCl3F in the presence of AlCl3 yields heptachloro-7-(trifluoromethyl)naphthalene (4), which in CS2 and with an excess of AlCl3 affords 1. The spectra and X-ray crystal structure of chlorocarbon 1 are reported, as well as that of the much less strained heptachloro-7-(dichloromethyl)naphthalene (10). The unusual UV spectrum, due to the distortion of the aromatic rings, is also discussed. The reduction of 1 with copper wire to give perchloro(2-naphthyl)methyl radical (11) has been studied by means of electron spin resonance. Steric inhibition to resonance of the free electron within the aromatic ring in 11 has been estimated by a semiempirical AM1 method.