(2-methyl-5-((phenylselanyl)methyl)-4,5-dihydrofuran-3-yl)(phenyl)methanone | 146896-37-9

• 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-methyl-5-((phenylselanyl)methyl)-4,5-dihydrofuran-3-yl)(phenyl)methanone
• 英文别名: 3-benzoyl-4,5-dihydro-2-methyl-5-<(phenylseleno)methyl>furan；[5-Methyl-2-(phenylselanylmethyl)-2,3-dihydrofuran-4-yl]-phenylmethanone
• CAS: 146896-37-9
• 化学式: C₁₉H₁₈O₂Se
• 分子量: 357.311
• InChiKey: LMFHJMYTJYRFFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.38
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2-methyl-5-((phenylselanyl)methyl)-4,5-dihydrofuran-3-yl)(phenyl)methanone 在 双氧水 、 碳酸氢钠 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 苯 为溶剂， 反应 29.0h， 生成 3-benzoyl-2,5-dimethylfuran
  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：

  二苯基二硒醚 、 2-烯丙基-1-苯基-1,3-丁烷二酮 在 ammonium peroxydisulfate 作用下， 生成 (2-methyl-5-((phenylselanyl)methyl)-4,5-dihydrofuran-3-yl)(phenyl)methanone
  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

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。
• 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。
• Alcohol Substitution and Dehydrogenation of Selenium Compounds: A Convenient Preparation of Trisubstituted Furans from allyl-substituted 1,3-dicarbonyls
  作者：E Tang、Xian Huang

  DOI：10.3184/030823408x320629

  日期：2008.6

  Trisubstituted furans have been synthesised efficiently by an alcohol substitution and dehydrogenation reaction of selenocyclic enol ethers which were prepared by organoselenium-induced regioselective electrophilic intramolecular cyclisation of allyl-substituted 1,3-dicarbonyls.

  通过有机硒诱导的烯丙基取代 1,3 二羰基的亲电分子内环化反应，硒环烯醇醚发生醇取代和脱氢反应，从而高效合成了三取代呋喃。
• Elimination reactions of terminal .beta.-oxy selenoxides. Synthesis of aryl and vinyl enol ethers and of furans, oxazoles, and thiazoles
  作者：Marcello Tiecco、Lorenzo Testaferri、Marco Tingoli、Francesca Marini

  DOI：10.1021/jo00058a011

  日期：1993.3

  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.