2-methylselenane | 180588-50-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 金属杂环化合物
• 英文名称: 2-methylselenane
• 英文别名: 2-methyltetrahydro-2H-selenopyran；(+/-)-2-Methyl-tetrahydro-selenopyran
• CAS: 180588-50-5
• 化学式: C₆H₁₂Se
• 分子量: 163.121
• InChiKey: TVQANDHATBATBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  2-methylselenane 在 溴 作用下， 以 四氯化碳 、 苯 为溶剂， 以332 mg的产率得到1,1-dibromo-2-methylselenane
  参考文献：
  名称：

  (Aryltelluro)formates as Precursors of Alkyl Radicals:  Thermolysis and Photolysis of Primary and Secondary Alkyl (Aryltelluro)formates

  摘要：

  Alkyl (aryltelluro)formates are effective precursors of oxyacyl, methyl, and primary and secondary alkyl radicals. At room temperature, irradiation of a benzene solution of methyl (aryltelluro)formates 10-12, 2-methylpropyl (aryltelluro)formates 14 and 15, octyl (phenyltelluro)formate (17), cyclohexyl (aryltelluro)formates 19 and 20, 3 beta-cholestanyl (aryltelluro)formates 22 and 23, cholesteryl (phenyltelluro)formate (24) and benzyl (phenyltelluro)formate (27) with a 250-W low-pressure mercury lamp leads to the formation of oxyacyl radicals (34), which can be trapped by diphenyl diselenide to give the corresponding alkyl (phenylseleno)formates 13, 16, 18, 21, 24, 26, and 28 with excellent overall conversions. Thermolysis of these telluroformates at 160 degrees C in the dark leads to the formation of methyl and primary and secondary alkyl aryl tellurides 36-43 in excellent yields. Presumably, these transformations involve oxyacyl radicals, which undergo subsequent decarboxylation at the elevated temperature to afford alkyl radicals, which become involved in further radical chemistry. When 1-(benzylseleno)-5-hexyl (phenyltelluro)formate (44) was thermolysed under these conditions, 2-methylselenane (45) was observed as the sole selenium-containing product, demonstrating the synthetic utility of (aryltelluro)formates as alkyl radical precursors.

  DOI：

  10.1021/jo960838y
• 作为产物：
  描述：

  6-bromohexan-2-ol 以 四氢呋喃 、 乙醇 、 苯 为溶剂， 反应 337.0h， 生成 2-methylselenane
  参考文献：
  名称：

  (Aryltelluro)formates as Precursors of Alkyl Radicals:  Thermolysis and Photolysis of Primary and Secondary Alkyl (Aryltelluro)formates

  摘要：

  Alkyl (aryltelluro)formates are effective precursors of oxyacyl, methyl, and primary and secondary alkyl radicals. At room temperature, irradiation of a benzene solution of methyl (aryltelluro)formates 10-12, 2-methylpropyl (aryltelluro)formates 14 and 15, octyl (phenyltelluro)formate (17), cyclohexyl (aryltelluro)formates 19 and 20, 3 beta-cholestanyl (aryltelluro)formates 22 and 23, cholesteryl (phenyltelluro)formate (24) and benzyl (phenyltelluro)formate (27) with a 250-W low-pressure mercury lamp leads to the formation of oxyacyl radicals (34), which can be trapped by diphenyl diselenide to give the corresponding alkyl (phenylseleno)formates 13, 16, 18, 21, 24, 26, and 28 with excellent overall conversions. Thermolysis of these telluroformates at 160 degrees C in the dark leads to the formation of methyl and primary and secondary alkyl aryl tellurides 36-43 in excellent yields. Presumably, these transformations involve oxyacyl radicals, which undergo subsequent decarboxylation at the elevated temperature to afford alkyl radicals, which become involved in further radical chemistry. When 1-(benzylseleno)-5-hexyl (phenyltelluro)formate (44) was thermolysed under these conditions, 2-methylselenane (45) was observed as the sole selenium-containing product, demonstrating the synthetic utility of (aryltelluro)formates as alkyl radical precursors.

  DOI：

  10.1021/jo960838y

文献信息

• Transition-metal-free one-pot synthesis of alkynyl selenides from terminal alkynes under aerobic and sustainable conditions
  作者：Adrián A Heredia、Alicia B Peñéñory

  DOI：10.3762/bjoc.13.92

  日期：——

  Alkynyl selenides were synthesized by a straightforward one-pot and three-step methodology, without the need of diselenides as starting reagents, under an oxygen atmosphere and using PEG 200 as the solvent. This procedure involves the in situ generation of dialkyl diselenides through a K3PO4-assisted reaction of an alkyl selenocyanate obtained by a nucleophilic substitution reaction between KSeCN and

  在氧气气氛下，使用PEG 200作为溶剂，通过简单的一锅三步法合成炔基硒化物，不需要二硒化物作为起始试剂。该程序涉及通过KSeCN与卤代烷之间的亲核取代反应获得的硒代氰酸烷基酯的K3PO4辅助反应，原位生成二烷基二硒代烷。在t-BuOK存在下与末端炔烃的连续反应以中等至良好的产率得到相应的烷基炔基硒化物。最后，该方法允许从方便的2-取代的乙炔开始合成2-烷基硒基取代的苯并呋喃和吲哚衍生物。
• XXIII.—Heterocyclic systems containing selenium. Part IV. cycloSelenohexane
  作者：Gilbeet T. Morgan、Francis Hereward Burstall

  DOI：10.1039/jr9310000173

  日期：——