selenobenzophenone | 119579-98-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: selenobenzophenone
• 英文别名: Selenobenzophenon；Benzoselenophenone；diphenylmethaneselone
• CAS: 119579-98-5
• 化学式: C₁₃H₁₀Se
• 分子量: 245.182
• InChiKey: OWFCDQUCJXHNOQ-UHFFFAOYSA-N

物化性质

• 熔点：
  183 °C
• 沸点：
  335.3±25.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.42
• 重原子数：
  14
• 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

反应信息

• 作为反应物：
  描述：

  selenobenzophenone 在 苯基溴化镁 作用下， 以 甲苯 为溶剂， 生成 1,1,2,2-四苯乙烯
  参考文献：
  名称：

  硒代二苯甲酮与烷基锂的新反应生成对称烯烃

  摘要：

  硒代二苯甲酮与烷基锂或格氏试剂的反应专门提供对称的四芳基乙烯作为亲硒产物。该反应可能通过表硒化物（硒烷）中间体进行。

  DOI：

  10.1246/cl.1996.609
• 作为产物：
  描述：

  2,2,4,4-Tetraphenyl-1,3-diselenacyclobutan 以 氘代苯 为溶剂， 生成 selenobenzophenone
  参考文献：
  名称：

  Erker, Gerhard; Hock, Regina; Krueger, Carl, Angewandte Chemie, 1990, vol. 102, # 9, p. 1082 - 1084

  摘要：

  DOI：

文献信息

• Selenobenzophenones and Diazoalkanes: Isolation of Tetraarylethylenes by the Reaction of Benzophenone Hydrazones with Diselenium Dibromide
  作者：Kentaro Okuma、Kazuki Kojima、Kosuke Oyama、Kento Kubo、Kosei Shioji

  DOI：10.1002/ejoc.200300510

  日期：2004.2

  retrocyclization was observed. The formation of 1,3,4-selendiazolines was independently confirmed by the reaction of benzophenone hydrazones with diselenium dibromide, which afforded tetraarylethylenes in good yields. This method is applicable to the two-step synthesis of tetraarylethylenes from benzophenones. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

  硒代二苯甲酮与重氮甲烷反应得到相应的二芳基乙烯和对称烯烃。与二芳基重氮甲烷反应得到三种不同类型的四芳基乙烯。该反应通过 1,3,4-硒二唑啉中间体进行，并观察到逆环化。通过二苯甲酮腙与二溴化二硒的反应独立地证实了 1,3,4-硒二唑啉的形成，其以良好的产率提供了四芳基乙烯。该方法适用于二苯甲酮两步合成四芳基乙烯。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
• Stereospecific Reactions of Donor-Acceptor Cyclopropanes with Thioketones: Access to Highly Substituted Tetrahydrothiophenes
  作者：André U. Augustin、Maximilian Sensse、Peter G. Jones、Daniel B. Werz

  DOI：10.1002/anie.201708346

  日期：2017.11.6

  Lewis‐acid‐catalyzed reactions of 2‐substituted cyclopropane 1,1‐dicarboxylates with thioketones are described. Highly substituted tetrahydrothiophenes with two adjacent quaternary carbon atoms were obtained in a stereospecific manner under mild conditions and in high yield when using AlCl3 as Lewis acid. Moreover, an intramolecular approach was successfully implemented to gain access to sulfur‐bridged

  描述了路易斯酸催化的2-取代的环丙烷1,1-二羧酸酯与硫酮的反应。当使用AlCl 3作为路易斯酸时，在温和的条件下以立体有择的方式高产率地获得了具有两个相邻的季碳原子的高度取代的四氢噻吩。此外，成功地采用了分子内方法来获得硫桥[ n .2.1]双环系统。在类似条件下，硒酮（较重的类似物）的转化导致形成各种四氢硒代苯。
• Stereoselective synthesis of trans olefins by the reaction of Wittig reagents with selenium. Formation of selenocarbonyl compounds
  作者：Kentaro Okuma、Jun-ichi Sakata、Yuji Tachibana、Takumi Honda、Hiroshi Ohta

  DOI：10.1016/s0040-4039(00)96936-3

  日期：——

  Wittig reagents were successfully changed to symmetrical olefins when treated with elemental selenium. The reaction proceeds through a selenocarbonyl intermediate, which existence was confirmed by Diels-Alder reaction.

  用元素硒处理后，维蒂希试剂成功地转变为对称烯烃。反应通过硒代羰基中间体进行，这通过Diels-Alder反应确认。
• Reactions of selenobenzophenones with dimethyl acetylenedicarboxylate or norbornadiene
  作者：Kentaro Okuma、Kazuki Kojima、Isao Kaneko、Hiroshi Ohta

  DOI：10.1016/s0040-4039(00)91615-0

  日期：1992.3

  Reactions of selenobenzophenones with dimethyl acetylenedicarboxylate or norbornadiene gave benzoselenapyranes or seven-membered cyclic selenides; these reactions might proceed through unusual type of cycloaddition reaction.

  硒代二苯甲酮与乙酰二羧酸二甲酯或降冰片二烯的反应生成了苯并硒基吡喃或七元环硒化物；这些反应可能通过异常类型的环加成反应进行。
• Stereochemistry of the [4 + 2] Cycloaddition of Diarylselenoketones with Conjugated Dienes
  作者：Stefanie Wilker、Gerhard Erker

  DOI：10.1021/ja00149a015

  日期：1995.11

  The ylides Ph(3)P=(CArAr2)-Ar-1 1a-g (Ar C6H5, p-C6H4Cl p-C6H4F, m-C6H4CF3, P-C(6)H4OCH(3), p-C6H4CH3) were treated with elemental selenium (similar to 80 degrees C) to give the corresponding selenoketones Se=CAr(1)Ar2 2 by Staudinger-chalcogenation. Their reaction with trans,trans-2,4-hexadiene proceeds completely stereospecifically to yield the 2,2-diaryl-3,6-dihydro-cis-3,6-dimethyl-2H-selenapyrans 3. In contrast, the reactions of the selenoketones 2 with cis, trans-2,4-hexadiene proceeds stereoselectively, also giving the dihydro-cis-dimethyl-2H-selenapyrans 3 as the major products, now admired with small amounts of the dihydro-trans-dimethyl-2H-selenapyran isomers 4. The [4 + 2] cydoaddition of 2 with cis,trans-2,4-hexadiene proceeds stereospecifically, however, when carried out at a pressure of 12 kbar, now yielding 4 as the major products along with the corresponding tetraarylethenes 8. Along with the results of additional mechanistic studies (determination of solvent and substituent effects) it can be concluded that diarylselenoketones are likely to react by means of a concerted [4 + 2] cycloaddition with very reactive conjugated dienes (such as trans,trans-2,4-hexadiene), whereas a stepwise mechanism, resulting in diene cis/trans-isomerization with subsequent mechanistic ''leakage'' to the concerted pathway, appears to be preferred when a much less reactive conjugated diene such as cis,trans-2,4-hexadiene is employed. The reaction of the corresponding diarylthioketones 5a-g with trans,trans- and cis,trans-2,4-hexadiene, respectively, shows an analogous behavior.