2,6-Dimethyl-2-(phenylselanylmethyl)oxane | 114524-34-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 2,6-Dimethyl-2-(phenylselanylmethyl)oxane
• CAS: 114524-34-4
• 化学式: C₁₄H₂₀OSe
• 分子量: 283.272
• InChiKey: CEMMNILZKKMWIS-UHFFFAOYSA-N

物化性质

• 沸点：
  342.1±24.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.78
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  6-methylhept-6-en-2-ol 、 苯基溴化硒 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到2,6-Dimethyl-2-(phenylselanylmethyl)oxane
  参考文献：
  名称：

  使用吡啶、Ag2O 和一些路易斯酸作为催化剂对某些 α5-烯醇进行苯基硒醚化的改进方法

  摘要：

  已经开发了使用 PhSeX (X = Cl, Br) 对某些 Δ5-烯醇进行分子内环化的改进程序。我们发现在吡啶、Ag2O 和一些路易斯酸作为催化剂的存在下可以促进环化。因此，催化量的添加剂（吡啶和 Ag2O）会影响更高的产率，但在极其温和的实验条件下等摩尔量可实现几乎定量的产率。在路易斯酸（ZnCl2 和 FeCl3）的存在下，以催化量获得高产率的环醚产物。© 2004 Wiley Periodicals, Inc. 杂原子化学 15:146–149, 2004; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.10227

  DOI：

  10.1002/hc.10227

文献信息

• Electrochemical cyclization of unsaturated hydroxy compounds. Part I. Phenylselenoetherification
  作者：M.Lj. Mihailovic̀、S. Konstantinovic̀、R. Vukic̀evic̀

  DOI：10.1016/s0040-4039(00)96504-3

  日期：1987.1

  One-step cyclization of alkenols has been accomplished by electrooxidative phenylselenoetherification. The reaction was performed by electrolysis of unsaturated alcohols and diphenyl diselenide in methylene chloride containing tetraethylammonium bromide.

  烯醇的一步环化已通过电氧化苯基硒醚化完成。通过不饱和醇和二苯基二硒化物在含溴化四乙铵的二氯甲烷中的电解进行反应。
• An Efficient Route to Phenylselenoethers in the Presence of Ag2O
  作者：Zorica M. Bugarčić、Vera M. Divac、Mariana P. Gavrilović

  DOI：10.1007/s00706-007-0661-y

  日期：2007.10

  An efficient protocol for the preparation of phenylselenoethers from unsaturated alcohols using phenylselenenyl halides at room temperature was developed. The procedure employs phenylselenenyl chloride and bromide, some Δ 4- and Δ 5-alkenols and Ag2O, as an additive, to generate the tetrahydropyrans or tetrahydrofurans. This method permits the preparation of cyclic phenylselenoethers in high yields

  开发了一种在室温下使用苯基硒烯基卤化物从不饱和醇制备苯基硒醚的有效方案。该过程采用苯硒基氯化物和溴化物，一些Δ 4 -和Δ 5个-alkenols和Ag 2 O，作为添加剂，以产生所述的四氢吡喃或四氢呋喃。该方法允许在极温和的条件下以高收率制备环状苯基硒醚。
• Electrochemical cyclization of unsaturated hydroxy compounds. Phenylselenoetherification and phenylselenolactonization
  作者：R. Vukićevic、S. Konstantinovic、M.Lj. Mihailovic

  DOI：10.1016/s0040-4020(01)87074-5

  日期：1991.1

  Phenylselenoetherification and phenylselenolactonization were performed in one step by electrolysis of unsaturated alcohols or carboxylic acids and diphenyl diselenide in organic solvent containing halide ions as mediators.
• Bugarčić, Zorica; Konstantinović, Stanimir; Mojsilović, Biljana, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999, vol. 38, # 6, p. 728 - 731
  作者：Bugarčić, Zorica、Konstantinović, Stanimir、Mojsilović, Biljana

  DOI：——

  日期：——
• Phenylselenoetherification of Some ?5-Alkenols in the Presence of Pyridine, Ag2O, and AgOAc as Additives
  作者：Zorica M. Bugarcic、Marijana Gavrilovic

  DOI：10.1007/s00706-002-0596-2

  日期：2003.10.1

  An improved procedure for intramolecular cyclization of some Delta(5)-alkenols using PhSex (X = Cl, Br) was developed. We found that cyclization can be facilitated in the presence of pyridine, Ag2O, and AgOAc as additives. Thus, a catalytic amount of additive influenced higher yields and equimolar amounts achieved almost quantitative yields under extremely mild experimental conditions. The effect of the halide ion of the selenylating reagent was not significant.