3,6-dihydro-4,5-dimethyl-2-phenyl-2H-selenapyran | 112196-22-2

• 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: 3,6-dihydro-4,5-dimethyl-2-phenyl-2H-selenapyran
• 英文别名: 3,6-dihydro-2-phenyl-4,5-dimethyl-2H-selenin；3,6-dihydro-4,5-dimethyl-2-phenyl-2H-selena-pyran；4,5-dimethyl-2-phenyl-3,6-dihydro-2H-selenopyran
• CAS: 112196-22-2
• 化学式: C₁₃H₁₆Se
• 分子量: 251.23
• InChiKey: IVHRBDFKOOZHLF-UHFFFAOYSA-N

物化性质

• 沸点：
  311.2±42.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  α,α-二溴甲苯 在 sodium tetrahydroborate 、 四氯化锡 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 6.0h， 生成 3,6-dihydro-4,5-dimethyl-2-phenyl-2H-selenapyran
  参考文献：
  名称：

  氯化锡诱导的双（N，N-二甲基氨基甲酰硒）甲烷的不对称 CSe 键断裂：硒醛的新生成

  摘要：

  用 SnCl4 处理双（N,N-二甲基氨基甲酰硒）甲烷以中等至高产率获得 β-1,3,5-三硒烷，反应的关键中间体，即酰基硒离子和硒醛被成功捕获使用烯丙基三甲基硅烷或2,3-二甲基-1,3-丁二烯分别得到烯丙基化产物或环加合物。© 2006 Wiley Periodicals, Inc. 杂原子化学 17:125–135, 2006; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20190

  DOI：

  10.1002/hc.20190

文献信息

• 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。
• Reaction of phosphorus ylides with elemental selenium: generation of seleno aldehydes and selenium-catalyzed Ph3P:CHR cleavage to give RHC:CHR and triphenylphosphine
  作者：Gerhard. Erker、Regina. Hock、Rainer. Nolte

  DOI：10.1021/ja00210a066

  日期：1988.1

  Les selenals du titre sont pieges par le dimethyl-2,3butadiene-1,3 ou l'anthracene pour donner par addition de Diels Alder des heterocycles du selenium

  Les selenals du titre sont pieges par le dimethyl-2,3butadiene-1,3 ou l'anthracene pour donner par added de Diels Alder desheterocycles du selenium
• Convenient Syntheses of N,N-Dialkylselenoamides and N,N,N′,N′-Tetraalkylselenoureas by Treating Terminal<i>gem</i>-Dihaloalkanes, Chloroform, or Sodium Trichloroacetate with a Base, Elemental Selenium, and Amines
  作者：Yuji Takikawa、Minoru Yamaguchi、Tohru Sasaki、Kenji Ohnishi、Kazuaki Shimada

  DOI：10.1246/cl.1994.2105

  日期：1994.11

  Treatment of terminal gem-dihaloalkanes, chloroform, or sodium trichloroacetate with elemental selenium in the presence of NaH and an excess amount of primary or secondary amines gave selenoamides and selenoureas in modest yields.

  对终端gem-二卤烷、氯仿或三氯乙酸钠在NaH和过量的初级或次级胺存在下用元素硒处理，得到了中等产率的硒酰胺和硒脲。
• A Willgerodt–Kindler Type Selenation of Dihalomethane Derivatives, Chloroform, and Sodium Trichloroacetate by Treating with a Base, Elemental Selenium, and an Amine
  作者：Kazuaki Shimada、Minoru Yamaguchi、Tohru Sasaki、Kenji Ohnishi、Yuji Takikawa

  DOI：10.1246/bcsj.69.2235

  日期：1996.8

  Treatment of dihalomethane derivatives, chloroform, or sodium trichloroacetate with elemental selenium in the presence of NaH and an excess amount of an amine gave the corresponding selenoamides, selenoureas, and bis(selenocarbamoyl) triselenides in modest yields. These products were afforded from reactive intermediates related to “selenocarbonyl halides” and “selenophosgenoids” generated by the reaction of dichloromethanide ions and trichloromethanide ion with N-alkylated aminopolyselenide species (R2N–(Se)n−).

  处理二溴甲烷衍生物、氯仿或三氯乙酸钠与元素硒，配合氢化钠和过量胺，在适当条件下可得到相应的硒酰胺、硒脲和双（硒氨基）三硒化物，产率适中。这些产品来源于与“硒羰基卤化物”和“硒羰基氟化物”相关的活性中间体，这些中间体是二氯甲烷离子和三氯甲烷离子与N-烷基化氨基多硒化物（R2N–(Se)n−）反应生成的。
• 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。