hexachlorotropone | 21505-24-8

• 分子结构分类: 有机化合物 - 碳氢化合物衍生物 - 环庚三烯酮
• 英文名称: hexachlorotropone
• 英文别名: Hexachlortropon；perchlorotropone；Perchlor-tropon；2,3,4,5,6,7-Hexachlorocyclohepta-2,4,6-trien-1-one
• CAS: 21505-24-8
• 化学式: C₇Cl₆O
• 分子量: 312.794
• InChiKey: WGSYUYMYPJFQHE-UHFFFAOYSA-N

物化性质

• 熔点：
  85 °C
• 沸点：
  165.6±40.0 °C(Predicted)
• 密度：
  1.82±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  hexachlorotropone 在 硫酸 、 水 、 氯 作用下， 生成 2,3-dihydroxyoctachlorocyclohept-2-en-1-one
  参考文献：
  名称：

  PENTACHLOROTROPOLONE AND 3-HYDROXYPENTACHLOROTROPONE

  摘要：

  五氯代托酚酮（3）是通过用浓硫酸处理八氯环庚三烯（1）得到的。将3在液氯中氯化得到了全氯化的七元还原酮（12）。光解4-羟基五氯二环[3.2.0]庚-3,6-二烯-2-酮（18）得到了3-羟基五氯托酚酮（19）。

  DOI：

  10.1246/cl.1982.1119
• 作为产物：
  描述：

  八氯环庚三烯 以 水 、 三氟乙酸 为溶剂， 反应 5.0h， 以96%的产率得到hexachlorotropone
  参考文献：
  名称：

  Drueecke, Stefan; Imming, Peter; Kaempchen, Thomas, Chemische Berichte, 1988, vol. 121, p. 1595 - 1600

  摘要：

  DOI：

文献信息

• [4 + 2] Cycloaddition reactions of hexachlorotropone
  作者：M. Akhtar、D.M. Bratby、J.C. Chadwick、G.I. Fray

  DOI：10.1016/0040-4020(76)85144-7

  日期：1976.1

  The cycloaddition of hexachlorotropone to selected olefins, including 1,3-dienes, has been examined. Unlike tropone, which undergoes [6 + 4] cycloadditions with 1,3-dienes, only [4 + 2] processes were observed with hexachlorotropone. Its apparent preference for exo-addition (contrast tetrachlorocyclopentadienone) probably results from thermodynamic control of the endo : exo product ratios.

  已经研究了六氯四氢环酮与包括1，3-二烯在内的所选烯烃的环加成反应。与托克酮与1,3-二烯经历[6 + 4]环加成反应不同，六氯托酮仅观察到[4 + 2]过程。其表观偏好外-addition（对比度tetrachlorocyclopentadienone）可能导致从热力学控制内：外产物比。
• The alkyne-anion promoted ring-contraction of hexachlorotropone: synthesis and structure of [trimethylsilyl(pentachlorobenzoyl)ethyne]-hexacarbonyldicobalt
  作者：James A Dunn、Laura E Harrington、Michael J McGlinchey

  DOI：10.1016/j.jorganchem.2003.09.033

  日期：2004.1

  The reaction of hexachlorotropone with trimethylsilylethynyl-lithium leads to contraction of the seven-membered ring via a semibenzilic acid rearrangement to yield pentachlorophenyl trimethylsilylethynyl ketone, 4. Treatment of 4 with dicobalt octacarbonyl yields the corresponding alkyne-dicobalt hexacarbonyl, 6, which has been characterized by X-ray crystallography.

  六氯四氢萘酮与三甲基甲硅烷基乙炔基-锂的反应通过半苯甲酸重排导致七元环收缩，生成五氯苯基三甲基甲硅烷基乙炔基酮4。用二羰基八钴二羰处理4，得到相应的炔-二钴六羰基6，已通过X射线晶体学表征。
• Reactions of Dimethoxycarbene with Cyclic Perchlorinated Olefins and Ketones
  作者：James A. Dunn、John Paul Pezacki、Michael J. McGlinchey、John Warkentin

  DOI：10.1021/jo9823846

  日期：1999.6.1

  Reactions of dimnethoxycarbene (2), a carbonyl group equivalent, with perchlorinated olefins and ketones were investigated. Thermolysis of 2,2-dimethoxy-5,5-dimethyl-Delta(3)-1,3,4-oxadiazoline (1) at 110 degrees C generated 2, which reacted with hexachlorocyclopentadiene (4), octachlorocycloheptatriene (12), octachlolobicyclo[3.2.0]hepta-3,6-diene (24), hexachlorotropone (28), hexachlorobicyclo[3.2.0]-hepta-3,6-dien-2-one (32), and tetrachloro-1,4-benzoquinone (35). Reactions of 2 with perchlorinated olefins 4, 12, and 24 led to esters or, in the case of 12, to a ketene acetal. Their formation is rationalized in terms of Michael-like addition and displacement (S(N)2' or S(N)2", if concerted) of allylic chlorine atoms by 2, yielding ion pairs that either dechloromethylate to esters or dechlorinate to a ketene acetal, In contrast, the reactions of 2 with unsaturated perchloroketones 28, 32, and 35 led to ring contraction, ring expansion, and aromatization, respectively. The products from these reactions are consistent with nucleophilic addition of 2 at the carbonyl moiety rather than Michael-type addition. Dimethoxycarbene-d(3) was used to show that demethylation in the latter reaction was intermolecular. Mechanisms for the different reaction courses are proposed.
• Octachlorocycloheptatriene and related compounds
  作者：Robert West、Kousuke Kusuda、V. N. Mallikarjuna Rao

  DOI：10.1021/ja00744a014

  日期：1971.7
• Lou, Yan; He, Yigang; Kendall, John T., Journal of Organic Chemistry, 2003, vol. 68, # 10, p. 3891 - 3895
  作者：Lou, Yan、He, Yigang、Kendall, John T.、Lemal, David M.

  DOI：——

  日期：——

表征谱图