3-carbethoxy-4,5-dihydro-2-phenyl-5-<(phenylseleno)methyl>furan | 146896-34-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 3-carbethoxy-4,5-dihydro-2-phenyl-5-<(phenylseleno)methyl>furan
• 英文别名: ethyl 2-phenyl-5-((phenylselanyl)methyl)-4,5-dihydrofuran-3-carboxylate；ethyl-2-phenyl-5-((phenylselanyl)methyl)-4,5-dihydrofuran-3-carboxylate；Ethyl 5-phenyl-2-(phenylselanylmethyl)-2,3-dihydrofuran-4-carboxylate
• CAS: 146896-34-6
• 化学式: C₂₀H₂₀O₃Se
• 分子量: 387.337
• InChiKey: PTQDLUXJUOUCKG-UHFFFAOYSA-N

物化性质

• 沸点：
  498.5±45.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-carbethoxy-4,5-dihydro-2-phenyl-5-<(phenylseleno)methyl>furan 在 双氧水 、 碳酸氢钠 作用下， 以 甲醇 、 苯 为溶剂， 反应 25.0h， 生成 3-carbethoxy-4,5-dihydro-2-phenyl-5-methylenefuran
  参考文献：
  名称：

  Elimination reactions of terminal .beta.-oxy selenoxides. Synthesis of aryl and vinyl enol ethers and of furans, oxazoles, and thiazoles

  摘要：

  Elimination reactions of terminal selenoxides holding an alkoxy group in the beta position, RCH-(OR)CH2SeOPh, are usually difficult and can give rise to complex reaction mixtures. We report that these reactions take place more easily whenever the oxygen atom is linked to an unsaturated group (-CH=CHR, -Ar, -CR=O, -CH=NR). These selenoxides are easily available, and the elimination reaction was employed to effect useful syntheses of both open-chain and cyclic aryl and vinyl enol ethers. Moreover, by simple isomerization with acids or bases the cyclic derivatives can be transformed into the corresponding furans. The same procedure has been employed to synthesize substituted oxazoles and thiazoles also.

  DOI：

  10.1021/jo00058a011
• 作为产物：
  描述：

  碘苯 在 selenium 、 亚碘酰苯 作用下， 以 二氯甲烷 为溶剂， 生成 3-carbethoxy-4,5-dihydro-2-phenyl-5-<(phenylseleno)methyl>furan
  参考文献：
  名称：

  通过碘代苯介导的烯烃与二硒化物的分子内硒环化制备硒官能化杂环

  摘要：

  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。

  DOI：

  10.1016/j.cclet.2021.02.050

文献信息

• Electrochemical oxidative cyclization of olefinic carbonyls with diselenides
  作者：Zhipeng Guan、Yunkun Wang、Huamin Wang、Yange Huang、Siyuan Wang、Hongding Tang、Heng Zhang、Aiwen Lei

  DOI：10.1039/c9gc02665g

  日期：——

  The tandem cyclization of olefinic carbonyls with easily accessible diselenides facilitated by electrochemical oxidation has been successfully developed, which provides an environmentally friendly method for the construction of C–Se and C–O bonds simultaneously. A series of seleno dihydrofurans and seleno oxazolines, bearing fragile heterocycles, subtle C–I bonds and supernumerary vinyl groups, were

  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。
• 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。
• 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。
• Preparation of Heterocycles via Visible-Light-Driven Aerobic Selenation of Olefins with Diselenides
  作者：Qing-Bao Zhang、Pan-Feng Yuan、Liang-Lin Kai、Kai Liu、Yong-Liang Ban、Xue-Yang Wang、Li-Zhu Wu、Qiang Liu

  DOI：10.1021/acs.orglett.8b03738

  日期：2019.2.15

  The aerobic dehydrogenative cyclization of alkenes with easily accessible diselenides facilitated by visible light is reported. Notably, the features of this transition-metal-free protocol are pronounced efficiency and practicality, good functional group tolerance, atom economy, and high sustainability, since ambient air and visible light are adequate for the clean construction of five- and six membered heterocycles in yields of up to 98%.
• 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。