1,1,2,2-四-(4-氯-苯基)-乙烷 | 13144-33-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: 1,1,2,2-四-(4-氯-苯基)-乙烷
• 英文名称: 1,1,2,2-tetrakis(4-chlorophenyl)ethane
• 英文别名: 1-Chloro-4-[1,2,2-tris(4-chlorophenyl)ethyl]benzene
• CAS: 13144-33-7
• 化学式: C₂₆H₁₈Cl₄
• 分子量: 472.241
• InChiKey: PDYTYXBWHJLEMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.6
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 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：

  1,1,2,2-四-(4-氯-苯基)-乙烷 以 乙腈 为溶剂， 生成 p,p'-Dichlorodiphenylmethyl radical 、 4,4'-dichlorobenzhydrylium ion
  参考文献：
  名称：

  Photohomolysis and Photoionization of Substituted Tetraphenylethanes and C-C Fragmentation of 1,1,2,2-Tetra(p-R-phenyl)ethane Radical Cations (R=H, CH3, OCH3, Cl)

  摘要：

  On photolysis of a series of tetraphenylethanes in 2,2,2-trifluoroethanol (TFE) solution with 248 nm light, homolysis of the central C-C bond occurs to yield the corresponding substituted diphenylmethyl radicals, in a process requiring one quantum of light. A second process takes place under conditions of high photon fluxes, namely biphotonic photoionization to produce a radical cation, which subsequently undergoes efficient C-C scission of the aliphatic central bond to yield the radical and carbocation fragments. Photoionization and photohomolysis are the preferred processes of excited state deactivation in the solvents acetonitrile, TFE, and 1,1,1,3,3,3-hexafluoroisopropanol. The lifetime of the radical cation could be directly determined by following the formation rates of the fragments in solution. The cations were characterized by their UV absorption spectra and electrophilic reactivities.

  DOI：

  10.1002/(sici)1521-3765(19980710)4:7<1275::aid-chem1275>3.0.co;2-x
• 作为产物：
  描述：

  1,1’-亚甲基双(4-氯苯) 在 manganese(IV) oxide 作用下， 以 联苯 、 苯 为溶剂， 生成 1,1,2,2-四-(4-氯-苯基)-乙烷
  参考文献：
  名称：

  Oxidation by Solids. II. The Preparation of Either Tetraarylethanes or Diaryl Ketones by the Oxidation of Diarylmethanes with Manganese Dioxide

  摘要：

  DOI：

  10.1021/jo01038a009

文献信息

• Facile reductive coupling of benzylic halides with ferrous oxalate dihydrate
  作者：Jitender M. Khurana、Sushma Chauhan、Golak C. Maikap

  DOI：10.1039/b211792d

  日期：2003.5.15

  Facile reductive coupling of benzylic halides is reported with ferrous oxalate dihydrate in DMF or HMPA under nitrogen atmosphere at 155–160 °C. The coupling is proposed to proceed by two successive oxidative additions of benzylic halides to ferrous oxalate to give an intermediate organoiron complex which undergoes concerted dimerization to give the corresponding reductively coupled dimers in high yields.

  报道称，在氮气气氛下，使用二水合草酸亚铁在DMF或HMPA中，于155-160°C的温度下，可以轻松实现苄基卤化物的还原耦合反应。该耦合反应被认为是通过苄基卤化物对草酸亚铁的两次连续氧化加成，生成一种中间体有机铁配合物，该配合物随后经历协同二聚反应，以高产率得到相应的还原耦合二聚体。
• Generation and Reactivity Studies of Diarylmethyl Radical Pairs in Crystalline Tetraarylacetones via Laser Flash Photolysis Using Nanocrystalline Suspensions
  作者：Jin H. Park、Melissa Hughs、Tim S. Chung、A. Jean-Luc Ayitou、Vanessa M. Breslin、Miguel A. Garcia-Garibay

  DOI：10.1021/jacs.7b04449

  日期：2017.9.27

  The nanosecond electronic spectra and kinetics of the radical pairs from various crystalline tetraarylacetones were obtained using transmission laser flash photolysis methods by taking advantage of aqueous nanocrystalline suspensions in the presence of submicellar CTAB, which acts as a surface passivator. After showing that all tetraarylacetones react efficiently by a photodecarbonylation reaction

  使用透射激光闪光光解法，在亚胶束 CTAB 存在下，利用纳米晶水悬浮液作为表面钝化剂，获得了来自各种结晶四芳基丙酮的自由基对的纳秒电子光谱和动力学。在证明所有四芳基丙酮在结晶状态下通过光脱羰反应有效反应后，我们能够检测到约内的中间自由基对。我们的激光装置的 8 ns 激光脉冲。我们表明自由基对的固态光谱与在溶液中检测到的非常相似，λmax 在 330-360 nm 范围内。观察到固态动力学是双指数的，不受氧气存在或激光功率变化的影响。一个相对短暂的组件（0.3-1.
• Use of Isopropyl Alcohol as a Reductant for Catalytic Dehydoxylative Dimerization of Benzylic Alcohols Utilizing Ti−O Bond Photohomolysis
  作者：Keiichi Sumiyama、Naoyuki Toriumi、Nobuharu Iwasawa

  DOI：10.1002/ejoc.202100286

  日期：2021.5.7

  Titanium‐catalyzed dehydroxylative dimerization of benzylic alcohols using isopropyl alcohol as a reductant has been realized by photoirradiation. The key step is photohomolysis of the Ti−O bond, which enables the utilization of isopropyl alcohol as a hydrogen‐atom donor. The reaction can also proceed under visible‐light irradiation in the presence of thioglycolic acid as a ligand.

  通过异丙醇的光辐照已经实现了钛醇对苄基醇的钛催化脱羟基二聚作用。关键步骤是Ti-O键的光均解，这使得能够利用异丙醇作为氢原子供体。该反应还可以在巯基乙酸为配体的情况下在可见光照射下进行。
• Mechanism of thermal decomposition of dibenzhydryl oxalates
  作者：J. Warkentin、D. M. Singleton

  DOI：10.1139/v67-492

  日期：1967.12.15

  Dibenzhydryl oxalate and several of its para-substituted analogs were thermally decomposed in diphenylmethane, diphenyl ether, and in α-chloronaphthalene solution. Evolution of gas (mainly CO2) was...

  草酸二二苯甲基及其几种对位取代的类似物在二苯甲烷、二苯醚和α-氯萘溶液中热分解。气体（主要是 CO2）的逸出是……
• Molybdenum-Catalyzed Cross-Coupling of Benzyl Alcohols: Direct C–OH Bond Transformation via [2 + 2]-Type Addition and Elimination
  作者：Pan Zhou、Yuqiang Li、Tao XU

  DOI：10.1021/acs.orglett.2c01537

  日期：2022.6.17

  Traditional cross-couplings catalyzed by transition metal catalysts generally rely on the classic oxidative addition–transmetalation–reductive elimination process, which requires low-valent precious metals and an inert atmosphere and which initiates from carbon–alide or pesudo carbon–halide bonds. Herein, an unprecedented molybdenum–oxo-complex-catalyzed intermolecular cross-coupling of benzyl alcohols

  由过渡金属催化剂催化的传统交叉偶联通常依赖于经典的氧化加成-金属转移-还原消除过程，该过程需要低价贵金属和惰性气氛，并从碳-卤化物或拟碳-卤化物键引发。在此，报道了前所未有的钼-氧络合物催化苯甲醇的分子间交叉偶联。包括伯、仲和叔底物在内的各种醇可以在这些条件下有效地进行。对低价过渡金属敏感的几个官能团，如芳基卤化物，可以很好地耐受。机理研究和DFT计算表明分子内协同环化参与了反向[2 + 2]型消除过程。