2-(4-chlorophenyl)-4,5-dimethyl-3,6-dihydro-2H-selenopyran | 127275-33-6

• 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: 2-(4-chlorophenyl)-4,5-dimethyl-3,6-dihydro-2H-selenopyran
• CAS: 127275-33-6
• 化学式: C₁₃H₁₅ClSe
• 分子量: 285.675
• InChiKey: TWXQGDARBKUJPG-UHFFFAOYSA-N

物化性质

• 沸点：
  338.9±42.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.24
• 重原子数：
  15
• 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：

  3-氯代亚苄基二溴 在 四氯化锡 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 6.0h， 生成 2-(4-chlorophenyl)-4,5-dimethyl-3,6-dihydro-2H-selenopyran
  参考文献：
  名称：

  通过氯化锡诱导的双（N，N-二甲基氨基甲酰基硒基）甲烷的不对称C-Se键裂解产生新一代的硒醛

  摘要：

  用SnCl 4处理双（N，N-二甲基氨基甲酰基硒基）甲烷的苯或CH 2 Cl 2溶液可得到β-1,3,5-三硒烯，并成功地通过捕获了关键中间体酰基ls离子和硒醛烯丙基三甲基硅烷或2,3-二甲基-1,3-丁二烯分别获得烯丙基化产物或环加合物。

  DOI：

  10.1016/j.tetlet.2005.03.153

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。
• Stannic chloride-induced unsymmetrical CSe bond cleavage of bis(N,N-dimethylcarbamoylseleno)methanes: Novel generation of selenoaldehydes
  作者：Yaling Gong、Kazuaki Shimada、Hidenori Nakamura、Masamichi Fujiyama、Akihiro Kodama、Miyuki Otsuki、Rei Matsumoto、Shigenobu Aoyagi、Yuji Takikawa

  DOI：10.1002/hc.20190

  日期：——

  Treatment of bis(N,N-dimethylcar- bamoylseleno)methanes with SnCl4 afforded β-1,3,5-triselenanes in moderate to high yields, and the key intermediates of the reactions, i.e., acylselonium ions and selenoaldehydes, were successfully trapped by using allyltrimethylsilane or 2,3-dimethyl-1,3-butadiene to obtain the allylation products or the cycloadducts, respectively. © 2006 Wiley Periodicals, Inc. Heteroatom

  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
• Novel synthesis of 1,3,5-triselenanes from aldehydes, and novel generation of selenoaldehydes by fragmentation of 1,3,5-triselenanes
  作者：Yuji Takikawa、Akira Uwano、Hiroyuki Watanabe、Masaki Asanuma、Kazuaki Shimada

  DOI：10.1016/s0040-4039(01)93851-1

  日期：1989.1