cyclohexyl (phenylseleno)formate

• 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: cyclohexyl (phenylseleno)formate
• 英文别名: Cyclohexyl phenylselanylformate
• 化学式: C₁₃H₁₆O₂Se
• 分子量: 283.229
• InChiKey: DUWXULWKUYPCCU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.49
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  phenylselenocyclohexane 在 四(三苯基膦)钯 偶氮二异丁腈 作用下， 以 苯 为溶剂， 反应 18.0h， 生成 cyclohexyl (phenylseleno)formate
  参考文献：
  名称：

  Phenylselenotris(trimethylsilyl)silane and phenyltellurotris(trimethylsilyl)silane: versatile reagents for the preparation of phenylseleno- and phenyltelluro-formates

  摘要：

  苯基碲杂三(三甲基硅基)硅烷4和(4-氟苯基碲)三(三甲基硅基)硅烷5与甲基、2-甲基丙基、环己基和苯基取代的氯甲酸酯（7、11、15、19）在苯中，并在四(三苯基膦)钯(0)（4摩尔%）的存在下反应，以50-79%的产率得到相应的芳基碲甲酸酯（8、9、12、13、16、17、20、21）；该方法也适用于(苯基硒)甲酸酯和硒、碲酯的制备。

  DOI：

  10.1039/a704402j

文献信息

• Palladium-Mediated Reactions of Chloroformates with Phenylselenotris(trimethylsilyl)silane and Aryltellurotris(trimethylsilyl)silane:  Improved Procedure for the Preparation of (Phenylseleno)- and (Aryltelluro)formates
  作者：Carl H. Schiesser、Melissa A. Skidmore

  DOI：10.1021/jo980710b

  日期：1998.8.1
• (Aryltelluro)formates as Precursors of Alkyl Radicals:  Thermolysis and Photolysis of Primary and Secondary Alkyl (Aryltelluro)formates
  作者：Mathew A. Lucas、Carl H. Schiesser

  DOI：10.1021/jo960838y

  日期：1996.1.1

  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.
• Phenylselenotris(trimethylsilyl)silane and phenyltellurotris(trimethylsilyl)silane: versatile reagents for the preparation of phenylseleno- and phenyltelluro-formates
  作者：Carl H. Schiesser、Melissa A. Skidmore

  DOI：10.1039/a704402j

  日期：——

  Phenyltellurotris(trimethylsilyl)silane 4 and (4-fluorophenyltelluro)tris(trimethylsilyl)silane 5 react with methyl, 2-methylpropyl, cyclohexyl and phenyl substituted chloroformates (7, 11, 15, 19) in benzene and in the presence of tetrakis(triphenylphosphine)palladium(0) (4 mol%) to afford the corresponding aryltelluroformate (8, 9, 12, 13, 16, 17, 20, 21) in 50–79% yield; this procedure is also applicable to the preparation of (phenylseleno)formates and seleno- and telluro-esters.

  苯基碲杂三(三甲基硅基)硅烷4和(4-氟苯基碲)三(三甲基硅基)硅烷5与甲基、2-甲基丙基、环己基和苯基取代的氯甲酸酯（7、11、15、19）在苯中，并在四(三苯基膦)钯(0)（4摩尔%）的存在下反应，以50-79%的产率得到相应的芳基碲甲酸酯（8、9、12、13、16、17、20、21）；该方法也适用于(苯基硒)甲酸酯和硒、碲酯的制备。