1,2-dichloro-1,2-diphenylethylene | 13700-82-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1,2-dichloro-1,2-diphenylethylene
• 英文别名: 1,2-dichloro-1,2-diphenylethene；Dichlorodiphenylethylene；(1,2-dichloro-2-phenylethenyl)benzene
• CAS: 13700-82-8
• 化学式: C₁₄H₁₀Cl₂
• 分子量: 249.139
• InChiKey: FTIHFTVXYNBUSM-UHFFFAOYSA-N

物化性质

• 熔点：
  193-194 °C
• 沸点：
  104-106 °C(Press: 6.1 Torr)
• 密度：
  1.232±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 海关编码：
  2903999090

反应信息

• 作为反应物：
  描述：

  1,2-dichloro-1,2-diphenylethylene 在 四(三苯基膦)钯 、 potassium hydroxide 、 苯硼酸 作用下， 以 四氢呋喃 为溶剂， 以10 %的产率得到二苯基乙炔
  参考文献：
  名称：

  使用 Suzuki 偶联反应后用正丁基锂处理从四氯乙烯制备二苯乙炔的简明合成路线

  摘要：

  我们想报道一种新的二苯乙炔合成方法，其中四氯乙烯在 Pd 催化剂存在下与苯硼酸反应，然后进行后处理程序以提供粗产物，然后允许其通过 Cl 原子的卤素锂交换和锂和 Cl 原子的损失与正丁基锂反应，以获得所需的二苯乙炔，产率高。

  DOI：

  10.1093/chemle/upae043
• 作为产物：
  描述：

  三氯化苄 在 Bis[2-(dimethylamino)phenyl]azanide;carbanide;nickel(2+) 作用下， 以 氘代苯 为溶剂， 反应 0.08h， 以55%的产率得到1,2-dichloro-1,2-diphenylethylene
  参考文献：
  名称：

  钳式酰胺基双（胺）配体的镍配合物：化学计量和催化C ？的合成，结构和活性。卤代烷的C键形成反应

  摘要：

  控制！描述了新的钳制酰胺双（胺）配体的Ni II配合物。氯化镍配合物催化未活化的烷基卤化物与烷基格氏试剂的Kumada–Corriu–Tamao偶联，以及CH 2 Cl 2与烷基格氏试剂的双重C–C偶联（参见方案）。

  DOI：

  10.1002/chem.200802059

文献信息

• Aromatic substitution in ball mills: formation of aryl chlorides and bromides using potassium peroxomonosulfate and NaX
  作者：Robert Schmidt、Achim Stolle、Bernd Ondruschka

  DOI：10.1039/c2gc16508b

  日期：——

  Aryl chlorides and bromides are formed from arenes in a ball mill using KHSO5 and NaX (X = Cl, Br) as oxidant and halogen source, respectively. Investigation of the reaction parameters identified operating frequency, milling time, and the number of milling balls as the main influencing variables, as these determine the amount of energy provided to the reaction system. Assessment of liquid-assisted grinding conditions revealed, that the addition of solvents has no advantageous effect in this special case. Preferably activated arenes are halogenated, whereby bromination afforded higher product yields than chlorination. Most often reactions are regio- and chemoselective, since p-substitution was preferred and concurring side-chain oxidation of alkylated arenes by KHSO5 was not observed.

  芳基氯和芳基溴是通过在球磨机中使用KHSO5和NaX（X=Cl，Br）分别作为氧化剂和卤素源，从芳烃形成的。对反应参数的调查确定操作频率、研磨时间和研磨球数为主要影响变量，因为这些变量决定了向反应系统提供的能量。对液体辅助研磨条件的评估揭示，在这种特殊情况下，溶剂的添加没有优势效应。优先激活的芳烃被卤化，其中溴化得到的产物收率高于氯化。大多数反应具有区域选择性和化学选择性，因为更喜欢对位取代，而且没有观察到KHSO5对烷基化芳烃侧链的氧化作用。
• Inter- and Innermolecular Reactions of Chloro(phenyl)carbene
  作者：Murray G. Rosenberg、Udo H. Brinker

  DOI：10.1021/jo026521h

  日期：2003.6.1

  Supramolecular photolyses of 3-chloro-3-phenyl-3H-diazirine (8) were performed within cyclodextrin (CyD) hosts to determine whether these toroidal inclusion compounds could alter the reactivity of the ensuing carbene reaction intermediate, chloro(phenyl)carbene (9). Remarkably, no intramolecular products stemming from carbene 9 could be detected. Instead, modified CyDs were formed via so-called innermolecular

  在环糊精（CyD）宿主中进行了3-chloro-3-phenyl-3H-diazirine的超分子光解（8），以确定这些环糊精包合物是否可以改变随后的卡宾反应中间体氯（苯基）卡宾的反应性（9） ）。值得注意的是，没有检测到源自卡宾9的分子内产物。而是通过所谓的分子内反应形成修饰的CyD。因此，将重氮嗪8在各种常规溶剂中进行光解，以测定卡宾9的分子间反应性。相关结果用于合理化CyD分子内反应产物。
• Absolute kinetics of phenylchlorocarbene CH insertion reactions
  作者：Robert A. Moss、Shunqi Yan

  DOI：10.1016/s0040-4039(98)02196-0

  日期：1998.12

  Absolute rate constants, activation parameters, a kinetic isotope effect, and hybrid density functional theory computational results are presented for various CH insertion reactions of PhCCl.

  给出了PhCCl各种CH插入反应的绝对速率常数，活化参数，动力学同位素效应和杂化密度泛函理论计算结果。
• Solid-state organic reactions proceeding by pulverization: Oxidation and halogenation with iodosobenzene and inorganic solid-supports
  作者：Hajime Sohmiya、Takahide Kimura、Mitsue Fujita、Takashi Ando

  DOI：10.1016/s0040-4020(98)00844-8

  日期：1998.11

  Pulverization-activation method was employed to accelerate solid-state organic reactions. Crushing and grinding of solid mixtures of hydrogen halide-treated silica gels, iodosobenzene and organic substrates in the absence of a solvent brought about smooth and rapid reactions to give halogenated and/or oxidized products in good yields. Various sulfides were smoothly converted to sulfonyl chlorides in one step in excellent yields. The surface of silica gel activated by pulverization serves as a reaction field on which reagent molecules can effectively encounter with each other. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Spin selectivity in the oxygenation of singlet phenylhalocarbenes with oxygen
  作者：Taiki Makihara、Takayuki Nojima、Katsuya Ishiguro、Yasuhiko Sawaki

  DOI：10.1016/s0040-4039(02)02538-8

  日期：2003.1

  Singlet phenylhalocarbenes are shown to react with triplet oxygen and the apparent spin-forbidden oxygenation rates are strongly dependent on substituents, i.e. in the decreasing order of Br>Clmuch greater thanF for halogen and of p-NO2>Hmuch greater thanp-MeO for p-substituents. These results suggest the oxygenation of triplet halocarbene equilibrated with ground-state singlet, resulting in the first estimation of energy difference between the singlet and triplet states. (C) 2003 Elsevier Science Ltd. All rights reserved.