perchloro-3-vinylindene | 143617-72-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 英文名称: perchloro-3-vinylindene
• 英文别名: 1,1,2,4,5,6,7-Heptachloro-3-(1,2,2-trichloroethenyl)indene
• CAS: 143617-72-5
• 化学式: C₁₁Cl₁₀
• 分子量: 486.651
• InChiKey: RNFDXNFUSGLAGE-UHFFFAOYSA-N

物化性质

• 沸点：
  496.0±45.0 °C(Predicted)
• 密度：
  1.92±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  21
• 可旋转键数：
  1
• 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：
  0

反应信息

• 作为反应物：
  描述：

  perchloro-3-vinylindene 在 三氯化铝 、 磺酰氯 、 二氯化硫 作用下， 反应 10.0h， 以16%的产率得到perchloro-1-vinylindan
  参考文献：
  名称：

  Extensive chlorination of methylnaphthalenes, Friedel-Crafts alkylation of pentachlorobenzene by heptachloro(chloromethyl)naphthalenes, and related results

  摘要：

  The chlorination of 2-methylnaphthalene (1) and 1-methylnaphthalene (12) by means of Silberrad's reagent (initial components: SO2Cl2, S2Cl2, and AlCl3) has been performed. From 1 or 12, the following compounds have been synthesized for first time: nonachloro-3-(chloromethyl)-1,4-dihydronaphthalene (3), nonachloro-7-(chloromethyl)-1,4-dihydronaphthalene (4), perchloro-3-vinylindene (2), perchloro-1-vinylindan, nonachloro-4-(chloromethyl)-1,4-dihydronaphthalene (11), heptachloro-7-(chloromethyl)naphthalene (6), heptachloro-8-(chloromethyl)naphthalene (10), heptachloro-7-methylnaphthalene, heptachloro-8-methylnaphthalene, 2-(bromochloromethyl)heptachloronaphthalene, 1-(bromochloromethyl)heptachloronaphthalene, heptachloro-7-formylnaphthalene (24), heptachloro-8-formylnaphthalene (26), (2-heptachloronaphthyl) (pentachlorophenyl)methane (17), and (1-heptachloronaphthyl) (pentachlorophenyl)methane (20). Silberrad's reagent interconverts dihydronaphthalenes 3 and 4. The AlCl3-promoted Friedel-Crafts alkylation of pentachlorobenzene (16) by naphthalenes 6 and 10, giving diarylmethanes 17 and 20, respectively, takes place in mild conditions (refluxing CS2) although the substrate and the alkylating agents are highly crowded polychloro compounds. By heating (100-degrees-C) a mixture of 17, 16, and AlCl3, 1H-heptachloronaphthalene (18) and bis(pentachlorophenyl)methane were obtained. Aldehyde 24, treated with Rh(PPh3)3Cl, gave 2H-heptachloronaphthalene, which was prepared in pure form for the first time. Under similar treatment, aldehyde 26 gave 18. The X-ray structures of indene 2 and dihydronaphthalene 11 are reported and discussed. Some probable mechanisms, as ell as IR, UV, and H-1 NMR spectra data of the compounds synthesized, are presented.

  DOI：

  10.1021/jo00047a026
• 作为产物：
  描述：

  2-甲基萘 在 二氯化二硫 、 三氯化铝 、 磺酰氯 作用下， 反应 8.25h， 生成 perchloro-3-vinylindene
  参考文献：
  名称：

  Extensive chlorination of methylnaphthalenes, Friedel-Crafts alkylation of pentachlorobenzene by heptachloro(chloromethyl)naphthalenes, and related results

  摘要：

  The chlorination of 2-methylnaphthalene (1) and 1-methylnaphthalene (12) by means of Silberrad's reagent (initial components: SO2Cl2, S2Cl2, and AlCl3) has been performed. From 1 or 12, the following compounds have been synthesized for first time: nonachloro-3-(chloromethyl)-1,4-dihydronaphthalene (3), nonachloro-7-(chloromethyl)-1,4-dihydronaphthalene (4), perchloro-3-vinylindene (2), perchloro-1-vinylindan, nonachloro-4-(chloromethyl)-1,4-dihydronaphthalene (11), heptachloro-7-(chloromethyl)naphthalene (6), heptachloro-8-(chloromethyl)naphthalene (10), heptachloro-7-methylnaphthalene, heptachloro-8-methylnaphthalene, 2-(bromochloromethyl)heptachloronaphthalene, 1-(bromochloromethyl)heptachloronaphthalene, heptachloro-7-formylnaphthalene (24), heptachloro-8-formylnaphthalene (26), (2-heptachloronaphthyl) (pentachlorophenyl)methane (17), and (1-heptachloronaphthyl) (pentachlorophenyl)methane (20). Silberrad's reagent interconverts dihydronaphthalenes 3 and 4. The AlCl3-promoted Friedel-Crafts alkylation of pentachlorobenzene (16) by naphthalenes 6 and 10, giving diarylmethanes 17 and 20, respectively, takes place in mild conditions (refluxing CS2) although the substrate and the alkylating agents are highly crowded polychloro compounds. By heating (100-degrees-C) a mixture of 17, 16, and AlCl3, 1H-heptachloronaphthalene (18) and bis(pentachlorophenyl)methane were obtained. Aldehyde 24, treated with Rh(PPh3)3Cl, gave 2H-heptachloronaphthalene, which was prepared in pure form for the first time. Under similar treatment, aldehyde 26 gave 18. The X-ray structures of indene 2 and dihydronaphthalene 11 are reported and discussed. Some probable mechanisms, as ell as IR, UV, and H-1 NMR spectra data of the compounds synthesized, are presented.

  DOI：

  10.1021/jo00047a026

文献信息

• Extensive chlorination of methylnaphthalenes, Friedel-Crafts alkylation of pentachlorobenzene by heptachloro(chloromethyl)naphthalenes, and related results
  作者：R. Garcia、J. Riera、J. Carilla、L. Julia、E. Molins、C. Miravitlles

  DOI：10.1021/jo00047a026

  日期：1992.10

  The chlorination of 2-methylnaphthalene (1) and 1-methylnaphthalene (12) by means of Silberrad's reagent (initial components: SO2Cl2, S2Cl2, and AlCl3) has been performed. From 1 or 12, the following compounds have been synthesized for first time: nonachloro-3-(chloromethyl)-1,4-dihydronaphthalene (3), nonachloro-7-(chloromethyl)-1,4-dihydronaphthalene (4), perchloro-3-vinylindene (2), perchloro-1-vinylindan, nonachloro-4-(chloromethyl)-1,4-dihydronaphthalene (11), heptachloro-7-(chloromethyl)naphthalene (6), heptachloro-8-(chloromethyl)naphthalene (10), heptachloro-7-methylnaphthalene, heptachloro-8-methylnaphthalene, 2-(bromochloromethyl)heptachloronaphthalene, 1-(bromochloromethyl)heptachloronaphthalene, heptachloro-7-formylnaphthalene (24), heptachloro-8-formylnaphthalene (26), (2-heptachloronaphthyl) (pentachlorophenyl)methane (17), and (1-heptachloronaphthyl) (pentachlorophenyl)methane (20). Silberrad's reagent interconverts dihydronaphthalenes 3 and 4. The AlCl3-promoted Friedel-Crafts alkylation of pentachlorobenzene (16) by naphthalenes 6 and 10, giving diarylmethanes 17 and 20, respectively, takes place in mild conditions (refluxing CS2) although the substrate and the alkylating agents are highly crowded polychloro compounds. By heating (100-degrees-C) a mixture of 17, 16, and AlCl3, 1H-heptachloronaphthalene (18) and bis(pentachlorophenyl)methane were obtained. Aldehyde 24, treated with Rh(PPh3)3Cl, gave 2H-heptachloronaphthalene, which was prepared in pure form for the first time. Under similar treatment, aldehyde 26 gave 18. The X-ray structures of indene 2 and dihydronaphthalene 11 are reported and discussed. Some probable mechanisms, as ell as IR, UV, and H-1 NMR spectra data of the compounds synthesized, are presented.