4,5-dimethyl-2,2-diphenyl-3,6-dihydro-2H-selenopyran | 116897-07-5

• 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: 4,5-dimethyl-2,2-diphenyl-3,6-dihydro-2H-selenopyran
• 英文别名: 3,4-Dimethyl-6,6-diphenyl-2,5-dihydroselenopyran
• CAS: 116897-07-5
• 化学式: C₁₉H₂₀Se
• 分子量: 327.328
• InChiKey: ZVORNFYRVBHAIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.79
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  selenobenzophenone 在 selenium 作用下， 反应 18.0h， 生成 4,5-dimethyl-2,2-diphenyl-3,6-dihydro-2H-selenopyran
  参考文献：
  名称：

  Regioselective Synthesis of Bicyclic Diselenides by the Reaction of Phosphonium Ylides with Elemental Selenium

  摘要：

  Selenabicyclo[2.2.1]heptenes reacted with elemental selenium to produce unusual bicyclic diselenides in 30-40% yield. The reaction of phosphonium ylides with excess of elemental selenium also afforded bicyclic diselenides in good yields. The reactions might proceed via biradical intermediates.

  DOI：

  10.3987/com-90-5598

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)
• An Efficient Synthesis of Selenocarbonyl Compounds by the Treatment of Carbonyl Compounds with Bis[1,5-cyclooctanediylboryl] Selenide
  作者：Kazuaki Shimada、Norikazu Jin、Manabu Fujimura、Yumi Nagano、Eiichi Kudoh、Yuji Takikawa

  DOI：10.1246/cl.1992.1843

  日期：1992.9

  An efficient synthesis of selenoaldehydes, selenoketones, and selenoamides was achieved by the treatment of carbonyl compounds with bis[1,5-cyclooctanediylboryl] selenide.

  通过使用双[1,5-环辛二基硼烷]硒化物处理羰基化合物，实现了硒醛、硒酮和硒酰胺的高效合成。
• Efficient Synthesis of Selenocarbonyl Compounds by Treating Carbonyl Compounds with Bis(1,5-cyclooctanediylboryl) Selenide
  作者：Kazuaki Shimada、Norikazu Jin、Michiko Kawaguchi、Kumiko Dobashi、Yumi Nagano、Manabu Fujimura、Eiichi Kudoh、Tomonari Kai、Noboru Saito、Jun-ichi Masuda、Masaki Iwaya、Hiroyuki Fujisawa、Shigenobu Aoyagi、Yuji Takikawa

  DOI：10.1246/bcsj.70.197

  日期：1997.1

  Selenoaldehydes and selenoketones were generated in situ, by treating aldehydes or ketones, respectively, with bis(1,5-cyclooctanediylboryl) selenide; the resulting selenocarbonyl compounds were trapped with 2,3-dimethyl-1,3-butadiene to give the corresponding [4+2] cycloadducts. The treatment of amides, an ester, and ketones possessing bulky substituents with the reagent also afforded the corresponding selenoamides, a selenoester, and sterically protected selones, respectively, in modest yields. On the other hand, a similar treatment of cinnamaldehyde with the reagent gave the 2,3-dihydroselenophene derivative, which originated from a [4+2]-type self-dimerization of in situ generated 3-phenyl-2-propeneselenal.

  在原位生成硒醛和硒酮，通过将醛或酮与双(1,5-环辛烷二基)硒化物处理；由此得到的硒羰基化合物与2,3-二甲基-1,3-丁二烯反应，形成相应的[4+2]环加成物。将具有体积较大取代基的酰胺、酯和酮与该试剂处理，亦分别得到相应的硒酰胺、硒酯和体积保护的硒酮，产率适中。另一方面，将肉桂醛与该试剂处理，得到2,3-二氢硒苯衍生物，这源于原位生成的3-苯基-2-丙烯硒醛的[4+2]型自聚合反应。
• Preparation of cycloaddition chemistry of thio- and selenocarbonyls derived from reaction of elemental sulfur and selenium with stabilized α-halo anions
  作者：Matthew M. Abelman

  DOI：10.1016/0040-4039(91)80114-l

  日期：1991.12

  Reaction of diethyl chloromalonate with Cs2CO3 in the presence of elemental S8 or Sen generates the corresponding diethyl thioxo- or selenoxomalonates which are subsequently trapped in situ with various 1,3-dienes. Similarly, the chalcogen carbonyls can be prepared from other halogenated using DBU as the base and effectively trapped in Diels-Alder fashion with 2,3-dimethyl-1,3-butadiene (Table 2).

  氯丙二酸二乙酯与Cs 2 CO 3在元素S 8或Se n的存在下反应，生成相应的二乙基硫代肟酸或亚硒酸丙二酸酯，随后将其与各种1,3-二烯原位捕获。同样，硫族化合物羰基化合物可以用DBU作为碱从其他卤代物中制备，并以Diels-Alder方式有效地被2,3-二甲基-1,3-丁二烯捕获（表2）。
• 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。