2-(4-methoxyphenyl)-4,5-dimethyl-3,6-dihydro-2H-selenopyran | 127275-32-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(4-methoxyphenyl)-4,5-dimethyl-3,6-dihydro-2H-selenopyran
• CAS: 127275-32-5
• 化学式: C₁₄H₁₈OSe
• 分子量: 281.256
• InChiKey: REYCXLBCELECTI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2,4,6-Tris(4-methoxyphenyl)-1,3,5-triselenane 、 2,3-二甲基-1,3-丁二烯 反应 4.0h， 以60%的产率得到2-(4-methoxyphenyl)-4,5-dimethyl-3,6-dihydro-2H-selenopyran
  参考文献：
  名称：

  Novel synthesis of 1,3,5-triselenanes from aldehydes, and novel generation of selenoaldehydes by fragmentation of 1,3,5-triselenanes

  摘要：

  DOI：

  10.1016/s0040-4039(01)93851-1

文献信息

• 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。
• Silicon-Mediated Synthesis of Selenoaldehydes and Selenoacylsilanes and Their Hetero Diels–Alder Reactions
  作者：Alessandro Degl'Innocenti、Antonella Capperucci、Miriam Acciai、Caterina Tiberi

  DOI：10.1080/10426500902947989

  日期：2009.6.23

  Bis(trimethylsilyl)selenide (HMDSS) reacts efficiently with aldehydes in the presence of CoCl 2 .6H 2 O to afford selenoaldehydes, which are trapped as Diels–Alder adducts by different dienes. The reaction can be applied to acylsilanes, to afford selenoacylsilanes, isolated as their cycloadducts.

  双（三甲基甲硅烷基）硒化物 (HMDSS) 在 CoCl 2 .6H 2 O 的存在下与醛有效反应，得到硒醛，硒醛被不同的二烯以 Diels-Alder 加合物形式捕获。该反应可以应用于酰基硅烷，以提供硒酰基硅烷，作为它们的环加合物分离。
• Generation of Selenoaldehydes via Retro Diels–Alder Reaction and Their Behavior in the Reaction with Some Enophiles
  作者：Masahito Segi、Aojia Zhou、Mitsunori Honda

  DOI：10.1080/10426500590906283

  日期：2005.2.23

  Abstract The [4, 2] cycloadducts of selenoaldehydes and anthracene regenerate selenoaldehydes in situ quantitatively under neutral conditions via thermal retro Diels–Alder reaction. The reactions of selenoaldehydes generated by this method with 2-silyloxy-1,3-butadiene, 2-methoxyfuran, and 5-ethoxyoxazoles are described.

  摘要 [4, 2] 硒醛和蒽的环加合物在中性条件下通过热逆狄尔斯-阿尔德反应原位再生硒醛。描述了通过该方法生成的硒醛与 2-甲硅烷氧基-1,3-丁二烯、2-甲氧基呋喃和 5-乙氧基恶唑的反应。