nonachloro-3-(chloromethyl)-1,4-dihydronaphthalene | 143617-73-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: nonachloro-3-(chloromethyl)-1,4-dihydronaphthalene
• 英文别名: 1,1,2,4,4,5,6,7,8-Nonachloro-3-(chloromethyl)naphthalene
• CAS: 143617-73-6
• 化学式: C₁₁H₂Cl₁₀
• 分子量: 488.667
• InChiKey: QSGHCDOKKCOWPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  nonachloro-3-(chloromethyl)-1,4-dihydronaphthalene 在 硫酸 、 溴 、 tin(ll) chloride 作用下， 以 1,4-二氧六环 、 四氯化碳 、 苯甲腈 为溶剂， 反应 131.0h， 生成 1,2,3,4,5,6,8-heptachloronaphthalene
  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 16.0h， 生成 nonachloro-3-(chloromethyl)-1,4-dihydronaphthalene
  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

• Synthesis and dynamic NMR studies of heptachloro-7-(dihalomethyl)naphthalenes
  作者：R. García、J. Riera、J. Carilla、L. Juliá、F.J. Sánchez-Baeza、E. Molins

  DOI：10.1016/0040-4020(95)00078-m

  日期：1995.3

  Accordingly, the 1H NMR spectra of 5, 7, and 2-(bromochloromethyl)heptachloronaphthalene (9) are temperature dependent, displaying two singlets that collapse in a sharp singlet about 100°C. Although the two conformers of 5, 7, and 9 can be detected in solution, only the most stable of each pair, at least in the case of 7, is present in solid form (X-ray analysis). A dynamic 1H NMR study shows that the barriers

  九氯-3-（氯甲基）-1,4-二氢萘（1）和九氯-7-（氯甲基）-1,4-二氢萘（2）的光氯化得到九氯-3-（二氯甲基）-1,4-二氢萘（3）和九氯-7-（二氯甲基）-1,4-二氢萘（4）。通过SnCl 2 .2H 2 O对3和4进行脱氯，得到七氯-7-（二氯甲基）萘（5）。Br 2对七氯-7-甲基萘（6）的光溴化反应生成2-（溴甲基）七氯萘（8）或七氯7-（二溴甲基）萘（7），具体取决于反应时间。通过在AIBN存在下用NBS溴化6可以高产率地制备中间体8。7中的理论计算表明，存在两个在能量上受到大力支持的构象者，并且其中一个似乎比另一个更稳定。因此，5、7和2-（溴氯甲基）七氯萘（9）的1 H NMR光谱是温度依赖性的，显示出两个单峰在约100°C的锐角单峰中折叠。尽管所两种构象异构5，7，和9可以在溶液中检测到，至少每对中只有最稳定的一对（至少在7种情况下）以固体形式存在（X射线分析）。动态1
• 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.