diethyl 2,2'-diiodo-4,4'-biphenyldicarboxylate | 107106-76-3

• 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: diethyl 2,2'-diiodo-4,4'-biphenyldicarboxylate
• 英文别名: 2,2'-diiodo-biphenyl-4,4'-dicarboxylic acid diethyl ester；2,2'-Dijod-biphenyl-4,4'-dicarbonsaeure-diaethylester；Ethyl 4-(4-ethoxycarbonyl-2-iodophenyl)-3-iodobenzoate
• CAS: 107106-76-3
• 化学式: C₁₈H₁₆I₂O₄
• 分子量: 550.132
• InChiKey: CHZTUCIXNAQIJO-UHFFFAOYSA-N

物化性质

• 沸点：
  555.4±50.0 °C(Predicted)
• 密度：
  1.788±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl 2,2'-diiodo-4,4'-biphenyldicarboxylate 在 氢氧化钾 、 氯化亚砜 、 硼烷 、 铜 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 52.5h， 生成
  参考文献：
  名称：

  Synthesis and Characterization of Oligo(2,7-biphenylenylene-(E)-vinylene)s: Conjugated Oligomers Containing Antiaromatic 12-π Electron Units

  摘要：

  AbstractThe syntheses and the electronic properties of oligo(2,7‐biphenylenylene‐(E)‐vinylene)s are reported. According to our spectral analysis, a limit of 2.5 ev for the peak band‐gap of poly(2,7‐biphenylenylene‐(E)‐vinylene)s is estimated. In addition, we discovered that oligo(2,7‐biphenylenylene‐(E)‐vinylene)s are amphoteric and can be either oxidized or reduced electrochemically.

  DOI：

  10.1002/jccs.199700033
• 作为产物：
  描述：

  联苯二甲酸二甲酯 在 硫酸 、 silver sulfate 作用下， 反应 60.0h， 生成 diethyl 2,2'-diiodo-4,4'-biphenyldicarboxylate
  参考文献：
  名称：

  Synthesis and Characterization of Oligo(2,7-biphenylenylene-(E)-vinylene)s: Conjugated Oligomers Containing Antiaromatic 12-π Electron Units

  摘要：

  AbstractThe syntheses and the electronic properties of oligo(2,7‐biphenylenylene‐(E)‐vinylene)s are reported. According to our spectral analysis, a limit of 2.5 ev for the peak band‐gap of poly(2,7‐biphenylenylene‐(E)‐vinylene)s is estimated. In addition, we discovered that oligo(2,7‐biphenylenylene‐(E)‐vinylene)s are amphoteric and can be either oxidized or reduced electrochemically.

  DOI：

  10.1002/jccs.199700033

文献信息

• Formation of 4-Methylphenanthrenes in Palladium-Catalyzed Annulation of Diethyl 2,2‘-Diiodo-4,4‘-biphenyldicarboxylate with Internal Alkynes, Using Methyl Nitrobenzoates as the Methylating Agent
  作者：Ashis Baran Mandal、Gene-Hsiang Lee、Yi-Hung Liu、Shie-Ming Peng、Man-kit Leung

  DOI：10.1021/jo991100u

  日期：2000.1.1

  The reaction of diethyl 2,2'-diiodo-4,4'-biphenyldicarboxylate (7) with diarylacetylenes in the presence of 3,5-(NO2)(2)C6H3CO2Me (MeDNB) or 4-(NO2)C6H4CO2Me (MePNB), Pd(OAc)(2) (10 mol %), K2CO3, and Bu4NBr, in DMF at 100 degrees C, gives 4-methyl-9,10-diaryl-2,7-phenanthrenediccarboxylic acid diethyl esters in good yields. The methyl group at position 4 originates from the electron-deficient methyl nitrobenzoates. High regioselectivity for the annulation of 7 with nonsymmetrical diarylalkynes was observed with the selectivity controlled mainly by electronic factors rather than by steric factors. A competitive kinetic isotope study was carried out using a 1:1 mixture of MePNB and MePNB-d(3) in the annulation reaction of 7 which gave 4-methyl- and 4-(methyl-d(3))phenanthrene in a 67:33 ratio, leading to an apparent value of k(H)/k(D) = 1.26. Possible mechanisms for the methyl transferring process are discussed.
• Stereochemistry of Diphenyls. XXX.¹ Preparation and Resolution of 2,2'-Diiodo-4,4'-dicarboxydiphenyl
  作者：N. E. Searle、Roger Adams

  DOI：10.1021/ja01331a055

  日期：1933.4
• Synthesis and Characterization of Oligo(2,7-biphenylenylene-(<i>E</i>)-vinylene)s: Conjugated Oligomers Containing Antiaromatic 12-π Electron Units
  作者：Chi-Yuen Kwong、Tze-Lock Chan、Hak-Fun Chow、Shi-Chun Lin、Man-Kit Leung

  DOI：10.1002/jccs.199700033

  日期：1997.6

  AbstractThe syntheses and the electronic properties of oligo(2,7‐biphenylenylene‐(E)‐vinylene)s are reported. According to our spectral analysis, a limit of 2.5 ev for the peak band‐gap of poly(2,7‐biphenylenylene‐(E)‐vinylene)s is estimated. In addition, we discovered that oligo(2,7‐biphenylenylene‐(E)‐vinylene)s are amphoteric and can be either oxidized or reduced electrochemically.