2-phenyl-5-((phenylselanyl)methyl)-4,5-dihydrooxazole | 123883-85-2

• 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: 2-phenyl-5-((phenylselanyl)methyl)-4,5-dihydrooxazole
• 英文别名: 2-Phenyl-5-(phenylselanylmethyl)-4,5-dihydro-1,3-oxazole
• CAS: 123883-85-2
• 化学式: C₁₆H₁₅NOSe
• 分子量: 316.261
• InChiKey: CLHJIXIFNWUZOZ-UHFFFAOYSA-N

物化性质

• 沸点：
  437.1±27.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.28
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-phenyl-5-((phenylselanyl)methyl)-4,5-dihydrooxazole 在 偶氮二异丁腈 三苯基氢化锡 作用下， 反应 3.0h， 以80%的产率得到5-Methyl-2-phenyl-2-oxazoline
  参考文献：
  名称：

  Organoselenium- and proton-mediated cyclization reactions of allylic amides and thioamides. Syntheses of 2-oxazolines and 2-thiazolines

  摘要：

  A variety of allylic amides and thioamides were treated with phenylselenenyl bromide in chloroform to give, via 5-exo cyclization, 2-oxazolines and 2-thiazolines, respectively, carrying a (phenylselenenyl)methyl substituent in the 5-position. In some cases (N-crotyl- and N-cinnamylamides/thioamides), dihydro-1,3-oxazines/-thiazines were formed via 6-endo cyclization. The phenylselenenyl group of the cyclofunctionalization products was slowly eliminated by treatment with m-chloroperbenzoic acid to introduce unsaturation in the resulting oxazoline/thiazoline. Reductive removal of the phenylselenenyl group was effected by treatment with triphenyltin hydride. This reaction was sometimes accompanied by a rearrangement of the heterocyclic ring. Proton-induced cyclizations of allylic thioamides to give 2-thiazolines was slowly but efficiently effected in boiling toluene containing a catalytic amount of p-toluenesulfonic acid.

  DOI：

  10.1021/jo00010a045
• 作为产物：
  描述：

  苯甲酰氯 在 2,2,2-三氟乙醇 、 tetrabutylammonium tetrafluoroborate 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 2.0h， 生成 2-phenyl-5-((phenylselanyl)methyl)-4,5-dihydrooxazole
  参考文献：
  名称：

  烯烃羰基与二硒化物的电化学氧化环化†

  摘要：

  已经成功地开发了通过电化学氧化促进具有容易获得的二硒化物的烯烃羰基的串联环化反应，这为同时构建C-Se和C-O键提供了一种环境友好的方法。使用这种优雅的螯合策略，可以伪造一系列带有易碎杂环，微妙的C–I键和大量乙烯基的硒代二氢呋喃和硒代恶唑啉。既不需要金属催化剂也不需要外部化学氧化剂来促进这种转变。

  DOI：

  10.1039/c9gc02665g

文献信息

• 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。
• Time-economical synthesis of selenofunctionalized heterocycles <i>via</i> I₂O₅-mediated selenylative heterocyclization
  作者：Chen-Fan Zhou、Yun-Qian Zhang、Yong Ling、Liang Ming、Xia Xi、Gong-Qing Liu、Yanan Zhang

  DOI：10.1039/d1ob02196f

  日期：——

  A time-economical and robust synthesis of various selenofunctionalized heterocycles was accomplished via I2O5-mediated selenocyclizations of olefins with diselenides. Using this method, 116 selenomethyl-substituted heterocycles were synthesized with up to 97% isolated yield in minutes. Additional features of this new protocol include the use of an inorganic oxidant, mild conditions, and easy operation

  通过I 2 O 5介导的烯烃与二硒化物的硒环化，实现了各种硒官能化杂环的经济且稳健的合成。使用这种方法，在几分钟内合成了 116 个硒甲基取代的杂环，分离产率高达 97%。这个新协议的其他特点包括使用无机氧化剂、温和的条件和易于操作。初步研究表明，这种转化是通过硒基碘诱导的亲电环化进行的。
• Electrochemical Chalcogenation of <i>β,γ</i> ‐Unsaturated Amides and Oximes to Corresponding Oxazolines and Isoxazolines
  作者：Samrat Mallick、Mrinmay Baidya、Kingshuk Mahanty、Debabrata Maiti、Suman De Sarkar

  DOI：10.1002/adsc.201901262

  日期：2020.3.4

  The current report represents a transition‐metal‐free synthesis of oxazoline and isoxazoline derivatives by a tandem electro‐oxidative chalcogenation‐cyclization process. Both C−Se and C−S bond‐forming protocols were developed without using any external oxidant and the reaction was performed at room temperature, open to the air. Using this methodology, 29 substituted oxazoline and 16 substituted isoxazoline

  本报告显示了通过串联电氧化硫属元素化-环化过程的无过渡金属合成恶唑啉和异恶唑啉衍生物。C-Se和C-S键形成方案均不使用任何外部氧化剂而开发，并且反应在室温下进行，并且对空气开放。使用这种方法，合成了29个取代的恶唑啉和16个取代的异恶唑啉衍生物，分离产率高达91％。
• Iodosobenzene Diacetate and Diphenyl Diselenide: An Electrophilic Selenenylating Agent of Double Bonds
  作者：Marco Tingoli*、Marcello Tiecco、Lorenzo Testaferri、Andrea Temperini

  DOI：10.1080/00397919808007007

  日期：1998.5

  Abstract Phenylseleno-acetoxylation, hydroxylation, etherification and lactonization products are obtained in good yields from the reaction of alkenes with diphenyl diselenide and iodosobenzene diacetate, in acetonitrile. present address: Dipartimento di Scienza degli Alimenti, Universita di Napoli “Federico II” Via Universita, 100 - 80055-Portici, Napoli-Italy. e-mail [e-mail].

  摘要 烯烃与二苯基二硒化物和碘代苯二乙酸酯在乙腈中反应，可得到苯硒-乙酰氧基化、羟基化、醚化和内酯化产物，收率良好。当前地址：Dipartimento di Scienza degli Alimenti, Universita di Napoli “Federico II” Via Universita, 100 - 80055-Portici, Napoli-Italy。电子邮件 [e-mail]。
• Ring-closure reactions initiated by the peroxydisulfate ion oxidation of diphenyl diselenide
  作者：Marcello Tiecco、L. Testaferri、M. Tingoli、D. Bartoli、R. Balducci

  DOI：10.1021/jo00289a010

  日期：1990.1