1-phenyl-2-(2-vinylphenyl)ethanone | 66657-90-7

• 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-phenyl-2-(2-vinylphenyl)ethanone
• 英文别名: Ethanone, 2-(2-ethenylphenyl)-1-phenyl-；2-(2-ethenylphenyl)-1-phenylethanone
• CAS: 66657-90-7
• 化学式: C₁₆H₁₄O
• 分子量: 222.287
• InChiKey: SDDBDAXOFAFFHW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-phenyl-2-(2-vinylphenyl)ethanone 在 臭氧 作用下， 以 二氯甲烷 为溶剂， 生成 ethyl 2-(benzoylmethyl)cinnamate
  参考文献：
  名称：

  Ozonolyses of 1,2-diphenyl- and 2-phenylindene

  摘要：

  Ozonolyses of 1,2-diphenylindene (7), 2-phenylindene (18), and the structurally related acyclic keto olefins 13, 14, 26, and 32 were conducted in MeOH/CH2Cl2 at -70 and 0-degrees-C. The structure of the indenes, 7 and 18, and the reaction temperature, were found to exert an influence on the outcome of the reaction. Ozonolysis of 1,2-diphenylindene (7) at -70-degrees-C proceeded exclusively via the carbonyl oxide intermediate 15 providing the methanol-derived isochroman 9a as the sole isolable product. In contrast, four methanol-derived products, 20-23, were obtained from 2-phenylindene (18) under similar reaction conditions, suggesting that the primary ozonide 25 from 18 undergoes two competing modes of decomposition. Ozonolyses of indenes, 7 and 18, and 0-degrees-C gave mainly the corresponding ozonides, 8 and 19, respectively, while analogous reactions at -70-degrees-C resulted in the predominant formation of the methanol-derived products 9 and 20-23, respectively. The major differences in composition between the ozonolysis product mixtures derived from the acyclic keto olefins 13, 14, 26, and 32 and the appropriate corresponding indenes 7 and 18 suggest that the intermediate carbonyl oxides generated from the former do not make significant contributions to the reaction pathways of the latter.

  DOI：

  10.1021/jo00053a026
• 作为产物：
  描述：

  2-苯基茚 生成 1-phenyl-2-(2-vinylphenyl)ethanone
  参考文献：
  名称：

  Photochemical transformations of small ring heterocyclic compounds. 93. Spatial requirements associated with the intramolecular 1,1-cycloaddition reactions of nitrile ylides

  摘要：

  DOI：

  10.1021/ja00475a032

文献信息

• Gold(I)-Catalyzed Cascade Cycloadditions between Allenamides and Carbonyl-Tethered Alkenes: An Enantioselective Approach to Oxa-Bridged Medium-Sized Carbocycles
  作者：Hélio Faustino、Isaac Alonso、José L. Mascareñas、Fernando López

  DOI：10.1002/anie.201302713

  日期：2013.6.17

  Gold standard: Allenamides react with aldehydes or ketones having γ, δ, or ε alkenyl groups, upon activation with suitable gold catalysts, to provide oxa‐bridged systems containing seven‐ to nine‐membered carbocycles, in a formal cascade cycloaddition. By using chiral phosphoramidite/gold or bisphosphine/gold catalysts it is possible to obtain the oxa‐bridged seven‐ and eight‐membered rings with good

  金标准：在适当的金催化剂活化后，烯丙酰胺与具有γ，δ或ε烯基的醛或酮反应，以正式的级联环加成反应提供含7至9元碳环的氧杂桥连体系。通过使用手性亚磷酰胺/金或双膦/金催化剂，可以获得具有良好至高对映选择性的氧杂桥联的七元和八元环。
• Copper-catalyzed acylations of o-vinylbenzylzirconocene intermediate and synthetic application toward steroid skeleton
  作者：Yutaka Ikeuchi、Takeo Taguchi、Yuji Hanzawa

  DOI：10.1016/j.tetlet.2004.04.049

  日期：2004.5

  Benzylzirconocene intermediate, which was readily prepared by a reaction of o-alkoxymethylstyrene with `Cp2Zr' under mild conditions, reacted with acyl chlorides in the presence of a catalytic amount of CuBr–SMe2 to give ketone derivatives in moderate to good yields.

  苄基锆茂新中间体很容易通过邻烷氧基甲基苯乙烯与“ Cp 2 Zr”在温和的条件下反应制备，并在催化量的CuBr-SMe 2存在下与酰氯反应，以中等至良好的收率得到酮衍生物。