(Z)-1,1,4,4-tetrakis(4-chlorophenyl)-2,3-dichloro-2-butene | 36954-66-2

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: (Z)-1,1,4,4-tetrakis(4-chlorophenyl)-2,3-dichloro-2-butene
• 英文别名: 1,1,4,4-tetrakis(4-chlorophenyl)-2,3-dichloro-2-butene；TTDB (Z)；(Z)-2,3-Dichloro-1,1,4,4-tetrakis-(4-chlorophenyl)but-2-ene；1-chloro-4-[(Z)-2,3-dichloro-1,4,4-tris(4-chlorophenyl)but-2-enyl]benzene
• CAS: 36954-66-2
• 化学式: C₂₈H₁₈Cl₆
• 分子量: 567.169
• InChiKey: GTVUABAMGVJSQR-DQSJHHFOSA-N

物化性质

• 熔点：
  171 °C
• 沸点：
  657.3±55.0 °C(Predicted)
• 密度：
  1.392±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  滴滴涕 在 三乙醇胺 、 C₅₂H₇₅CoN₄O₁₄⁽¹⁺⁾*ClO₄^(1-) 、 rose bengal 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以44%的产率得到1-氯-4-[2-(4-氯苯基)乙烯基]苯
  参考文献：
  名称：

  Supramolecular system composed of B₁₂ model complex and organic photosensitizer: impact of the corrin framework of B₁₂ on the visible-light-driven dechlorination without the use of noble metals

  摘要：

  The visible-light-driven dechlorination system without the use of a noble metal has been developed. We screened the combination of cobalt catalysts having square-planar monoanionic ligands (hydrophobic B-12 model complex 1/imine-oxime type complex 2) and typical red dyes (Rose Bengal 3/Rhodamine B 4/Nile Red 5) for the construction of a dehalogenation system via a noble-metal-free and visible-light-driven process. The combination of the hydrophobic B-12 model complex 1 and Rose Bengal 3 exhibited the highest catalytic activity to 1,1-bis(4-chlorophenyl)-2,2,2-trichloroethane (DDT) to form the monodechlorinated compound, 1,1-bis(4-chlorophenyl)-2,2-dichloroethane, as the major product. The prolonged photocatalysis of DDT by the B-12-Rose Bengal system afforded the tri-dechlorinated compound, trans-4,4-dichlorostilbene, as the major product. Furthermore, we investigated the mechanism of the dehalogenation cycle using various methods such as UV-vis spectroscopy and laser flash photolysis. Finally, we clarified the advantage of using the hydrophobic B-12 model complex 1 as an electron acceptor as well as a cobalt catalyst in the organic dye-involved photocatalysis.

  DOI：

  10.1080/10610278.2015.1103373

文献信息

• B₁₂–TiO₂Hybrid Catalyst for Dehalogenation of Organic Halides
  作者：Hisashi Shimakoshi、Emiko Sakumori、Kenji Kaneko、Yoshio Hisaeda

  DOI：10.1246/cl.2009.468

  日期：2009.5.5

  acid, was effectively immobilized on TiO 2 , and the hybrid Ti0 2 was characterized by UV―vis, XPS, MALDI-TOFMS as well as TEM analysis. The hybrid Ti0 2 exhibits high reactivity for dehalogenation of various organic halides such as phenethyl bromide, benzyl bromide, and 1,1-bis(4-chlorophenyl)-2,2,2-trichloroethane (DDT) under irradiation with UV light at room temperature.

  钴胺素衍生物cobyrinic acid 被有效地固定在TiO 2 上，并且通过UV-vis、XPS、MALDI-TOFMS 以及TEM 分析对杂化TiO 2 进行了表征。杂化TiO 2 在室温下紫外光照射下对苯乙基溴、苄基溴和1,1-双(4-氯苯基)-2,2,2-三氯乙烷(DDT)等各种有机卤化物的脱卤表现出高反应性温度。
• Photochemical dechlorination of DDT catalyzed by a hydrophobic vitamin B12 and a photosensitizer under irradiation with visible light
  作者：Hisashi Shimakoshi、Mami Tokunaga、Tatsushi Baba、Yoshio Hisaeda

  DOI：10.1039/b406400c

  日期：——

  Dechlorination of 1,1-bis(4-chlorophenyl)-2,2,2-trichloroethane (DDT) was catalyzed by a hydrophobic vitamin B(12), heptamethyl cobyrinate perchlorate, with a visible light irradiation system containing a [Ru(ii)(bpy)(3)]Cl(2) photosensitizer, and the hydrophobic vitamin B(12) showed high catalytic efficiency and stability during the reaction.

  1,1-双（4-氯苯基）-2,2,2-三氯乙烷（DDT）的脱氯反应是通过疏水性维生素B（12），高甲基邻苯二甲酸酯七氯酸盐和可见光照射系统进行的，该可见光照射系统包含[Ru（ii） ）（bpy）（3）] Cl（2）光敏剂和疏水性维生素B（12）在反应过程中显示出高催化效率和稳定性。
• Sensitized photolyses of DDT and decyl bromide
  作者：Larry L. Miller、Raginder S. Narang、Gerald D. Nordblom

  DOI：10.1021/jo00942a030

  日期：1973.1
• Supramolecular system composed of B₁₂ model complex and organic photosensitizer: impact of the corrin framework of B₁₂ on the visible-light-driven dechlorination without the use of noble metals
  作者：Keishiro Tahara、Kumiko Mikuriya、Takahiro Masuko、Jun-ichi Kikuchi、Yoshio Hisaeda

  DOI：10.1080/10610278.2015.1103373

  日期：2016.2.1

  The visible-light-driven dechlorination system without the use of a noble metal has been developed. We screened the combination of cobalt catalysts having square-planar monoanionic ligands (hydrophobic B-12 model complex 1/imine-oxime type complex 2) and typical red dyes (Rose Bengal 3/Rhodamine B 4/Nile Red 5) for the construction of a dehalogenation system via a noble-metal-free and visible-light-driven process. The combination of the hydrophobic B-12 model complex 1 and Rose Bengal 3 exhibited the highest catalytic activity to 1,1-bis(4-chlorophenyl)-2,2,2-trichloroethane (DDT) to form the monodechlorinated compound, 1,1-bis(4-chlorophenyl)-2,2-dichloroethane, as the major product. The prolonged photocatalysis of DDT by the B-12-Rose Bengal system afforded the tri-dechlorinated compound, trans-4,4-dichlorostilbene, as the major product. Furthermore, we investigated the mechanism of the dehalogenation cycle using various methods such as UV-vis spectroscopy and laser flash photolysis. Finally, we clarified the advantage of using the hydrophobic B-12 model complex 1 as an electron acceptor as well as a cobalt catalyst in the organic dye-involved photocatalysis.