(1S)-1,3,3-trimethylbicyclo[2.2.1]heptane-2-selone | 56956-24-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1S)-1,3,3-trimethylbicyclo[2.2.1]heptane-2-selone
• 英文别名: selenofenchone；1,3,3-trimethylnorbornane-2-selone；1,3,3-Trimethylnorbornan-2-selon；(1R,4S)-1,3,3-trimethylbicyclo[2.2.1]heptane-2-selone
• CAS: 56956-24-2
• 化学式: C₁₀H₁₆Se
• 分子量: 215.197
• InChiKey: GNMCDOCXUWTHLT-OIBJUYFYSA-N

物化性质

• 沸点：
  235.5±23.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.17
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 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：

  (1S)-1,3,3-trimethylbicyclo[2.2.1]heptane-2-selone 在 溴化硒 作用下， 以 二氯甲烷 为溶剂， 以88%的产率得到1,2-bis(7,7-dimethyl-2-methylenemethylenebicyclo[2.2.1]heptan-1-yl)diselenide
  参考文献：
  名称：

  Reaction of Fenchone Hydrazone with Diselenium Dibromide: Novel Formation of Bicyclic Diselenide

  摘要：

  DOI：

  10.3987/com-13-12888
• 作为产物：
  描述：

  (1R)-1,3,3-三甲基二环[2.2.1]庚-2-酮 在 三乙胺 、 肼 、 溴化硒 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 (1S)-1,3,3-trimethylbicyclo[2.2.1]heptane-2-selone
  参考文献：
  名称：

  Reaction of Fenchone Hydrazone with Diselenium Dibromide: Novel Formation of Bicyclic Diselenide

  摘要：

  DOI：

  10.3987/com-13-12888

文献信息

• Reaction of Ketone Hydrazones with Diselenium Dihalides: Simple Synthesis of Δ³-1,3,4-Selenadiazolines and 2,5-Diarylselenophenes
  作者：Kentaro Okuma、Toshiharu Izaki、Kento Kubo、Kosei Shioji、Yoshinobu Yokomori

  DOI：10.1246/bcsj.78.1121

  日期：2005.6

  by one-pot reactions of ketone hydrazones with diselenium dibromide, which suggested the in situ formation of selone and diazoalkane intermediates. The thermolysis of these compounds gave symmetrical olefins, whereas oxidation afforded the corresponding azines. The reaction of acetophenone hydrazones with diselenium dibromide afforded 2,5-diarylselenophenes in moderate yields. The reaction proceeded

  通过酮腙与二溴化二硒的一锅反应分离了空间拥挤的顺式和反式-Δ 3 -1,3,4-硒二唑啉，这表明selone和重氮烷中间体的原位形成。这些化合物的热解得到对称烯烃，而氧化得到相应的吖嗪。苯乙酮腙与二溴化二硒反应以中等产率得到2,5-二芳基硒吩。反应通过单独的中间体进行。
• 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。
• Synthesis of Dialkenyl Dichalcogenides via Alkenechalcogenolate Ions Generated by Treating Ketone p-Toluenesulfonylhydrazones with a Base and Elemental Chalcogen
  作者：Kazuaki Shimada、Mitsuharu Asahida、Ken Takahashi、Yoshitaka Sato、Shigenobu Aoyagi、Yuji Takikawa、Chizuko Kabuto

  DOI：10.1246/cl.1998.513

  日期：1998.6

  Alkeneselenolate and alkenetellurolate ions were generated by treating ketone p-toluenesulfonylhydrazones possessing an α-methylene or an α-methine group with t-BuOK and elemental selenium or tellurium, respectively, at 110-150 °C, and were converted into dialkenyl dichalcogenides by aerobic oxidation.

  通过分别用 t-BuOK 和元素硒或碲处理具有 α-亚甲基或 α-次甲基基团的酮对甲苯磺酰腙，分别在 110-150 °C 下产生烯硒烯酸和烯四烯酸离子，并通过好氧转化为二烯基二硫属化物氧化。
• “Tied-back” carbocyclic intermediates in the preparation of very sterically strained olefins: Derivatives of tetra--butylethylene
  作者：Edward R. Cullen、Frank S. Guziec、Mitchell I. Hollander、Christopher J. Murphy

  DOI：10.1016/s0040-4039(01)82982-8

  日期：1981.1

  The preparations of the extremely sterically hindered olefins (12) and-(13) are described, and attempts to convert these compounds to other derivatives of tetra--butylethylene (1) are outlined.

  描述了极受空间阻碍的烯烃（12）和-（13）的制备，并概述了将这些化合物转化为四-丁基乙烯（1）的其他衍生物的尝试。
• Synthesis and properties of monomeric selenoketones
  作者：Thomas G. Back、Derek H. R. Barton、Michael R. Britten-Kelly、Frank S. Guziec

  DOI：10.1039/c39750000539

  日期：——

  The preparation and reactions of di-t-butyl selenoketone (Ib) and of (–)-selenofenchone (IIb) are described; fenchylidenefenchane (VI) has been synthesised.

  描述了二叔丁基硒酮（Ib）和（-）-硒烯酮（IIb）的制备和反应；fenchylidenefenfenchane（VI）已合成。