2,6-dichloro-1-(1-undecyl)benzene

• 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: 2,6-dichloro-1-(1-undecyl)benzene
• 英文别名: 1,3-Dichloro-2-undecylbenzene
• 化学式: C₁₇H₂₆Cl₂
• 分子量: 301.299
• InChiKey: SAKWCGJPHVBVBJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  19
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 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：

  1,3-Dichloro-2-((E)-undec-1-enyl)-benzene 在 platinum on activated charcoal 氢气 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 2,6-dichloro-1-(1-undecyl)benzene
  参考文献：
  名称：

  Synthesis and Diatropicity of trans-10b-Methyl-10c-undecyl- and trans-10b-Methyl-10c-pentadecyl-10b,10c-dihydropyrene. An Empirical Approach to a Semiquantitative Assessment of the Diamagnetic Ring Current in a [14]Annulene

  摘要：

  trans-10b-Methyl-10c-undecyl- and trans-10b-methyl-10c-pentadecyl-10b,10c-dihydropyrene, 3b and 3c, were obtained from the valence isomerization of their corresponding [2.2]cyclophanedienes 28a and 28b. The long internal alkyl chain in each case was previously introduced via a Wittig reaction followed by reduction. The cyclophanedienes were synthesized from their corresponding dithia-[3.3]cyclophanes via a Wittig rearrangement-Hofmann elimination sequence. Proton chemical shifts of H1' to H9' of the alkyl chains in 3b and 3c, respectively, are identical, suggesting that the C1'-C9' section of the long alkyl chain in 3b or 3c has similar averaged conformational movement. Application of the Johnson-Bovey (J-B) model to 3b does not give a satisfactory correlation between the proton ring current shift and the out-of-plane distance. A direct empirical plot of the out-of-plane distance, D, against the proton ring current shifts, Delta delta, however, gives a curve similar to that obtained from the J-B model of benzene. This curve in fact corresponds to a linear relationship between D and log \Delta delta\. Calculated ring current shifts of several derivatives of 10b,10c-dihydropyrene based on the above empirical correlation agree well with the reported experimental values. Our model shows that the experimental detectable limit for the diatropicity of 10b,10c-dihydropyrene is about 14 Angstrom from the mean molecular plane. A similar empirical treatment based on the carbon chemical shifts of the n-undecyl chain in 3b gives unsatisfactory results. Our model does not support the prediction that the magnitude of ring current effect on proton and carbon chemical shifts is essentially the same at the sample position in space relative to the mean plane of delocalization of an aromatic pi-electron cloud.

  DOI：

  10.1021/jo9612382

文献信息

• Iron(III)-Catalyzed Ortho-Preferred Radical Nucleophilic Alkylation of Electron-Deficient Arenes
  作者：Fei Yu、Ting Wang、Huan Zhou、Yajun Li、Xinhao Zhang、Hongli Bao

  DOI：10.1021/acs.orglett.7b03244

  日期：2017.12.15

  ortho-preferred, radical alkylation of electron-deficient (hetero)arenes is reported. A variety of electron-deficient arenes were shown to react with various primary alkyl sources, producing the alkylated (hetero)arenes in good yields. This reaction might be an alkyl radical, nucleophilic aromatic substitution reaction, rather than the traditional electrophilic Friedel–Crafts reaction. HOMO–LUMO analysis and

  报道了缺电子（杂）芳烃的非传统铁催化的，邻位优选的自由基烷基化。已显示出各种电子不足的芳烃可与各种伯烷基源反应，以高收率生产烷基化（杂）芳烃。该反应可能是烷基自由基，亲核芳香取代反应，而不是传统的亲电Friedel-Crafts反应。关于区域选择性的关键过渡态的HOMO-LUMO分析和DFT研究与观察到的反应和结论一致。
• Synthesis and Diatropicity of <i>trans</i>-10b-Methyl-10c-undecyl- and <i>trans</i>-10b-Methyl-10c-pentadecyl-10b,10c-dihydropyrene. An Empirical Approach to a Semiquantitative Assessment of the Diamagnetic Ring Current in a [14]Annulene
  作者：Yee-Hing Lai、Zhao-Lin Zhou

  DOI：10.1021/jo9612382

  日期：1997.2.1

  trans-10b-Methyl-10c-undecyl- and trans-10b-methyl-10c-pentadecyl-10b,10c-dihydropyrene, 3b and 3c, were obtained from the valence isomerization of their corresponding [2.2]cyclophanedienes 28a and 28b. The long internal alkyl chain in each case was previously introduced via a Wittig reaction followed by reduction. The cyclophanedienes were synthesized from their corresponding dithia-[3.3]cyclophanes via a Wittig rearrangement-Hofmann elimination sequence. Proton chemical shifts of H1' to H9' of the alkyl chains in 3b and 3c, respectively, are identical, suggesting that the C1'-C9' section of the long alkyl chain in 3b or 3c has similar averaged conformational movement. Application of the Johnson-Bovey (J-B) model to 3b does not give a satisfactory correlation between the proton ring current shift and the out-of-plane distance. A direct empirical plot of the out-of-plane distance, D, against the proton ring current shifts, Delta delta, however, gives a curve similar to that obtained from the J-B model of benzene. This curve in fact corresponds to a linear relationship between D and log \Delta delta\. Calculated ring current shifts of several derivatives of 10b,10c-dihydropyrene based on the above empirical correlation agree well with the reported experimental values. Our model shows that the experimental detectable limit for the diatropicity of 10b,10c-dihydropyrene is about 14 Angstrom from the mean molecular plane. A similar empirical treatment based on the carbon chemical shifts of the n-undecyl chain in 3b gives unsatisfactory results. Our model does not support the prediction that the magnitude of ring current effect on proton and carbon chemical shifts is essentially the same at the sample position in space relative to the mean plane of delocalization of an aromatic pi-electron cloud.