1--2,2-diphenylethene | 133776-80-4

• 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--2,2-diphenylethene
• 英文别名: 1-(2,2-Diphenylethenyl)-4-methylsulfanylbenzene
• CAS: 133776-80-4
• 化学式: C₂₁H₁₈S
• 分子量: 302.44
• InChiKey: VNYMMMMQGZTANF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1--2,2-diphenylethene 在 溴 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以68%的产率得到1-bromo-1--2,2-diphenylethene
  参考文献：
  名称：

  Phenylthiolation of arylvinyl bromides by photolysis

  摘要：

  DOI：

  10.1021/jo00011a062
• 作为产物：
  描述：

  二苯基乙酰氯 在 三氯化铝 sodium hydroxide 、 sodium tetrahydroborate 、 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 99.5h， 生成 1--2,2-diphenylethene
  参考文献：
  名称：

  Phenylthiolation of arylvinyl bromides by photolysis

  摘要：

  DOI：

  10.1021/jo00011a062

文献信息

• Palladium- and Nickel-Catalyzed Kumada Cross-Coupling Reactions of <i>gem</i>-Difluoroalkenes and Monofluoroalkenes with Grignard Reagents
  作者：Wenpeng Dai、Juan Xiao、Guanyi Jin、Jingjing Wu、Song Cao

  DOI：10.1021/jo5022234

  日期：2014.11.7

  A novel Kumada–Tamao–Corriu cross-coupling reaction of gem-di- or monofluoroalkenes with Grignard reagents, with or without β-hydrogen atoms, in the presence of a catalytic amount of palladium- or nickel-based catalysts has been developed. The reaction is performed under mild conditions (room temperature or reflux in diethyl ether for 1–2 h) and leads to di-cross- or mono-cross-coupled products in

  在催化量的钯或镍基催化剂存在下，开发了一种新型的Kumada-Tamao-Corriu宝石二或单氟烯烃与Grignard试剂（含或不含β-氢原子）的交叉偶联反应。该反应在温和的条件下进行（室温或在乙醚中回流1–2小时），从而以高收率或高收率得到双交叉或单交叉偶联的产物。
• Electrochemical aerobic Wacker-type oxygenation of triaryl substituted alkenes to 1,2,2-triarylethanones
  作者：Zhou Zhang、Jin Li、Zhiwei Cai、Songyao Kang、Jian Wang、Yue Cui、Siyuan Han、Lei Sheng、Qing Yin、Ang Dai、Weining Zhao、Fangyuan Zhao

  DOI：10.1039/d3cc05770d

  日期：——

  An effective synthetic approach for various 1,2,2-triarylethanones from triaryl substituted alkenes has been developed via an electrochemical Wacker-type oxygenation with O2 as the sole oxygen source. It presents the first instance of the Wacker-type oxidation expanding its substrate scope to trisubstituted alkenes. The approach is transition-metal-free, compatible with various functional groups, and

  通过以 O 2作为唯一氧源的电化学瓦克型氧化，开发了一种从三芳基取代的烯烃中有效合成各种 1,2,2-三芳基乙酮的方法。它提出了瓦克型氧化将其底物范围扩展到三取代烯烃的第一个实例。该方法不含过渡金属，与各种官能团相容，并且可以在温和的条件下进行，从而获得令人满意的产率。机械实验表明 C O 键的形成是通过阳离子碳物质和超氧自由基之间的反应发生的，其中涉及富电子取代基的 1,2-位移。
• Organometallic compounds of Group III. XVI. Polar and stereochemical effects in the addition of triphenylaluminum to para-substituted diphenylacetylenes
  作者：John J. Eisch、Charles K. Hordis

  DOI：10.1021/ja00741a026

  日期：1971.6
• Ipso substitution of triarylvinyl cations by alkoxide anions
  作者：Tsugio Kitamura、Takashi Kabashima、Ichizo Nakamura、Tetsuro Fukuda、Hiroshi Taniguchi

  DOI：10.1021/ja00019a025

  日期：1991.9

  Photolysis and solvolysis of triarylbromoethanes 1 in the presence of alkoxide anions in alcohols resulted in significant formation of products derived from ipso substitution by alkoxide anions. Photolysis of 1-aryl-1-bromo-2,2-diphenylethenes 1Aa and 1Ab with 10 mol equiv of alkoxide anions gave 1-alkoxy-1-aryl-2,2-diphenylethenes 2A and 3,3-dialkoxy-6-(2,2-diphenylvinylidene)-1,4-cyclohexadienes 3A (ipso adducts). However, the photolysis with weak bases such as TEA, pyridine, NaHCO3, and K2CO3 did not give ipso adducts 3A but only enol ethers 2A. Interestingly, photolysis of 2,2-bis(p-alkoxyphenyl)-1-bromo-1-phenylethenes 4a and 4b with NaOEt in ethanol afforded ipso adducts 6a and 6b, respectively, which had a 1,2-aryl-rearranged structure. Furthermore, solvolysis of 1-bromo-1-(p-methoxyphenyl)ethenes 1Aa, 1Ba, and 1Ca in ethanol containing 10 mol equiv of NaOEt at 120-130-degrees-C for 1-3 days provided p-ethoxyphenyl-substituted enol ethers 2bb, p-ethoxyphenyl-substituted bromoethenes 1b, and p-methoxyphenyl-substituted enol ethers 2ab, respectively. The major formation of p-ethoxyphenyl-substituted compounds (ipso-substituted products) suggests that there is no large difference in ipso substitution between vinyl cations generated by photolysis and solvolysis. On the basis of the results obtained above the factors affecting ipso attack on arylvinyl cations are discussed.