Undecyl phenyl selenide | 53198-60-0

• 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: Undecyl phenyl selenide
• 英文别名: phenyl undecyl selenide；Undecylselanylbenzene
• CAS: 53198-60-0
• 化学式: C₁₇H₂₈Se
• 分子量: 311.369
• InChiKey: BREAQKQUBIKPFD-UHFFFAOYSA-N

物化性质

• 沸点：
  367.2±15.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.97
• 重原子数：
  18
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 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：

  苯硒酚 在 双氧水 作用下， 以 丙酮 、 苯 为溶剂， 生成 Undecyl phenyl selenide
  参考文献：
  名称：

  S H 2联苯二硒化物的反应；桥头硒化物的制备与反应

  摘要：

  对于S H 2过程，R·+ PhSeSePh→PhSeR + PhSe·，k = ca。当R为伯烷基时，在苯中80°C，5×10 7 mol –1 s –1；具有1-金刚烷基的该S H 2置换提供了通往1-金刚烷基苯基硒化物的途径，其在所得硒氧化物的氧化和热解后，产生了金刚烷-1-醇。与此相反，从双环的氧化硒[3.3.1]壬烷-1-基苯基硒化物分解经由二环[3.3.1]壬-1-烯。

  DOI：

  10.1039/c39810000139

文献信息

• A Novel and Highly Efficient Synthetic Route to Unsymmetrical Organoselenides Using Cesium Bases
  作者：Richard J. Cohen、Daniel L. Fox、Ralph Nicholas Salvatore

  DOI：10.1021/jo0401265

  日期：2004.6.1

  A new and convenient one-pot method for the preparation of unsymmetrical selenides has been developed. In the presence of cesium hydroxide, molecular sieves, and DMF, benzeneselenol undergoes direct alkylation with various alkyl halides for the synthesis of alkyl phenyl selenides in moderate to excellent yields. Another method to prepare unsymmetrical organoselenides was also completed by coupling terminal alkynes with benzeneselenyl bromide. As an application, the synthesis of a selenopeptide was also accomplished. Furthermore, this methodology was extended to the synthesis of an organoselenide on solid support.
• Seebach,D.; Beck,A.K., Angewandte Chemie, 1974, vol. 86, p. 859 - 860
  作者：Seebach,D.、Beck,A.K.

  DOI：——

  日期：——
• Rate constants for chalcogen group transfers in bimolecular substitution reactions with primary alkyl radicals
  作者：Dennis P. Curran、Amanda A. Martin-Esker、Sung Bo Ko、Martin Newcomb

  DOI：10.1021/jo00069a036

  日期：1993.8

  Rate constants for group transfers of the MeS, PhS, PhSe, and PhTe groups from chalcogen-substituted acetate, acetonitrile, malonate, and malononitrile compounds, from N-(phenylthio) phthalimide and from Me2S2 and Ph2S2 to primary alkyl radicals, have been determined by competition kinetics using PTOC esters as the radical precursors and competing trapping agents. Thio group transfers from malononitrile derivatives are marginally faster than the corresponding group transfer from the symmetrical disulfide, and the rate constant for PhSe group transfer from PhSeSePh is greater than those from the derivatives studied here. Substituent effects suggest that the chalcogen transfer reactions may be concerted. For three cases in which direct comparisons can be made, the rate constants for reactions of phenylchalcogenides are approximately equal to those for halogen atom transfer when the chalcogen and halide are in the same row of the periodic table and the radical resulting from displacement is the same. The rate constants reported in this work will be useful for the rational design of synthetic schemes based on homolytic group transfer chemistry.
• Synthesis of α-selenoalkyllithium compounds
  作者：A. Krief、W. Dumont、M. Clarembeau、G. Bernard、E. Badaoui

  DOI：10.1016/s0040-4020(01)80063-6

  日期：1989.1
• PERKINS M. J.; TURNER E. S., J. CHEM. SOC. CHEM. COMMUN., 1981 NO 3, 139-140
  作者：PERKINS M. J.、 TURNER E. S.

  DOI：——

  日期：——