(2-(phenylselanylmethyl)oxane) | 75526-73-7

• 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-(phenylselanylmethyl)oxane)
• 英文别名: 2-((phenylselanyl)methyl)tetrahydro-2H-pyran；2H-Pyran, tetrahydro-2-[(phenylseleno)methyl]-；2-(phenylselanylmethyl)oxane
• CAS: 75526-73-7
• 化学式: C₁₂H₁₆OSe
• 分子量: 255.218
• InChiKey: LRAOKELWNHJUIQ-UHFFFAOYSA-N

物化性质

• 沸点：
  332.1±24.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.0
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  甲醇 、 (2-(phenylselanylmethyl)oxane) 在 萘-1,4-二腈 作用下， 以80%的产率得到2-methoxymethyl-tetrahydro-pyran
  参考文献：
  名称：

  Photoinduced single electron transfer initiated heterolytic carbon-selenium bond dissociation. Sequential one-pot selenenylation and deselenenylation reaction

  摘要：

  DOI：

  10.1021/ja00170a045
• 作为产物：
  描述：

  苯基氯化硒 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 3.08h， 生成 (2-(phenylselanylmethyl)oxane)
  参考文献：
  名称：

  Formation and electrophilic reactions of benzeneselenenyl p-toluenesulfonate. Preparation and properties of addition products with acetylenes

  摘要：

  Benzeneselenenyl p-toluenesulfonate (1) was generated in situ by the reaction of silver p-toluenesulfonate with benzeneselenenyl chloride in acetonitrile. The reagent reacted with acetylenes by electrophilic 1,2-addition to afford the beta-(phenylseleno)vinyl p-toluenesulfonates 2-12, generally in high yield. The latter were formed preferentially by anti addition, but with poor regioselectivity, unless a strongly orienting group (e.g., phenyl) was present. Selenenyl sulfonate 1 was also unexpectedly produced via radical pathways by heating p-toluenesulfonic acid with AIBN in the presence of diphenyl diselenide, or from the pyrolysis of sulfinyl sulfone 15 with the diselenide. The regioisomeric adducts 3 and 4 were prepared from 1 and 1-decyne, and both underwent elimination with potassium tert-butoxide to afford the acetylenic selenide 19 initially, which isomerized to a 6:1 mixture of the propargylic and allenic selenides 20 and 21 upon further equilibration. A Fritsch-Buttenberg-Wiechell rearrangement is proposed for the elimination of 4. The syn elimination of the selenoxide of 4 required forcing conditions and afforded only ca. 20% of the corresponding allenic sulfonate 22. The electrophile 1 induced the efficient cyclization of 5-hexen-1-ol and 4-pentenoic acid to the corresponding pyran 24 and lactone 25, respectively. It failed to cyclize alkynols, but afforded the lactones 28 and 29 from 4-pentynoic acid in low yield.

  DOI：

  10.1021/jo00008a039

文献信息

• Automated Electrochemical Selenenylations
  作者：Thomas Wirth、Nasser Amri

  DOI：10.1055/s-0039-1690868

  日期：2020.6

  Integrated electrochemical reactors in automated flow systems were utilised for selenenylation reactions. The automation allowed multiple electrochemical reactions of a programmed sequence to be performed in a fully autonomous way. Many functionalised selenenylated­ products were synthesised in short reaction times in good to high yields.

  自动流动系统中的集成电化学反应器用于亚硒化反应。自动化允许以完全自主的方式执行程序化序列的多个电化学反应。在短的反应时间内以高到高的产率合成了许多官能化的亚硒化产物。
• Oxidative Cleavage of Diselenide by<i>m</i>-Nitrobenzenesulfonyl Peroxide. Novel Method for the Electrophilic Benzeneselenenylations of Olefins and Aromatic Rings
  作者：Masato Yoshida、Shuichi Sasage、Kyoko Kawamura、Takashi Suzuki、Nobumasa Kamigata

  DOI：10.1246/bcsj.64.416

  日期：1991.2

  acetic acid, phenol, and anisole could be employed; oxyselenenylated ((Remark: Graphics omitted.) : R=H, Me, Ac, and Ph) and arylselenenylated ((Remark: Graphics omitted.) : R=H and Me) adducts were afforded. Phenol gave oxyselenenylated products in cyclohexene or 1-octene and arylselenenylated products in styrene. Efficient intramolecular cyclizations of unsaturated alcohols and carboxylic acids were

  发现二苯基二硒化物通过用间硝基苯磺酰过氧化物处理很容易转化为间硝基苯磺酸苯硒基酯 (PhSeOSO2C6H4NO2-m)。当如此形成的硒基磺酸盐在各种亲核试剂的存在下与烯烃如环己烯、1-辛烯或苯乙烯原位反应时，得到苯硒基基团和亲核试剂的加合物。亲核试剂水、甲醇、乙酸、苯酚和苯甲醚均可使用；得到氧硒烯化（（备注：省略图示。）：R=H、Me、Ac 和 Ph）和芳​​基硒酰化（（备注：图示省略。）：R=H 和 Me）加合物。苯酚在环己烯或 1-辛烯中生成氧化硒化产物，在苯乙烯中生成芳基硒化产物。不饱和醇和羧酸的有效分子内环化同样通过磺酸硒进行，得到相应的苯硒化环醚和内酯。硒基磺酸盐也被发现是一种高...
• Oxidation of Diphenyl Diselenide with 2,3-Dichloro-5,6-dicyanobenzoquinone (DDQ). A New Method for the Electrophilic Phenylselenenylation of Alkenes under Mild Conditions
  作者：Marcello Tiecco、Lorenzo Testaferri、Andrea Temperini、Luana Bagnoli、Francesca Marini、Claudio Santi

  DOI：10.1055/s-2001-18091

  日期：——

  The oxidation of diphenyl diselenide with 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) represents a convenient mild method to produce a strongly electrophilic phenylselenium reagent. Clean phenylseleno methoxylations and hydroxylations of alkenes containing different types of functional groups can be effected by working in methanol or in acetonitrile and water, respectively. This new electrophilic reagent can also be employed to promote efficient cyclization reactions of alkenols to tetrahydrofurans or of alkenoic acids to lactones.

  二苯二硒化物与2,3-二氯-5,6-二氰苯醌（DDQ）的氧化反应是一种方便温和的方法，可以生成强亲电子性的苯基硒试剂。在甲醇或乙腈和水的条件下，可以对含有不同类型官能团的烯烃进行干净的苯基硒醚化和羟基化。这种新的亲电子试剂还可以用于促进烯醇向四氢呋喃或烯酸向内酯的高效环化反应。
• Organoselenium-induced cyclizations in organic synthesis
  作者：K.C. Nicolaou

  DOI：10.1016/s0040-4020(01)93285-5

  日期：——

  A number of organoselenium reagents are introduced as efficient initiators of ring closures leading from unsaturated substrates to lactones, cyclic ethers, cyclic thioethers, N-heterocycles and carbocycles. These cyclizations often proceed with high ring selectivity and stereoselectivity and are accompanied by the incorporation of the phenylseleno group (PhSe) into the final product. Methods are described

  引入了许多有机硒试剂，作为从不饱和底物到内酯，环醚，环硫醚，N-杂环和碳环的有效的环闭合引发剂。这些环化通常以高环选择性和立体选择性进行，并伴随有苯硒基（PhSe）结合到最终产物中。描述了通过氧化或还原以实现不饱和或饱和来有效去除该基团（PhSe）的方法。最后，概述了这种基于硒的方法在稳定和具有生物活性的前列环素的合成中的成功应用。包括代表性的实验程序。
• Preparation of selenofunctionalized heterocycles via iodosobenzene-mediated intramolecular selenocyclizations of olefins with diselenides
  作者：Peng-Fei Wang、Wei Yi、Yong Ling、Liang Ming、Gong-Qing Liu、Yu Zhao

  DOI：10.1016/j.cclet.2021.02.050

  日期：2021.8

  An intramolecular selenocyclizations of olefins mediated by a commercially available hypervalent iodine(III) reagent, PhIO, was developed. This method provided access to a wide range of selenenylated heterocycles under ambient conditions. The striking advantages of this protocol over all previous methods include mild reaction conditions, easy operation, good yields, high levels of functional group

  开发了由市售高价碘 (III) 试剂 PhIO 介导的烯烃分子内硒环化。该方法提供了在环境条件下获得多种硒基化杂环的途径。该协议相对于以前所有方法的显着优势包括反应条件温和、操作简单、产率高、官能团兼容性高、大规模应用以及适用于具有生物学重要性的复杂分子的后期功能化。