3-cyano-4,5-dihydro-2-phenyl-5-<(phenylseleno)methyl>furan | 123883-76-1

• 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: 3-cyano-4,5-dihydro-2-phenyl-5-<(phenylseleno)methyl>furan
• 英文别名: 2-phenyl-5-((phenylselanyl)methyl)-4,5-dihydrofuran-3-carbonitrile；5-Phenyl-2-(phenylselanylmethyl)-2,3-dihydrofuran-4-carbonitrile
• CAS: 123883-76-1
• 化学式: C₁₈H₁₅NOSe
• 分子量: 340.283
• InChiKey: OFEYIMHULVWDJY-UHFFFAOYSA-N

物化性质

• 沸点：
  473.4±45.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.16
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-cyano-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 18.0h， 生成 3-cyano-4,5-dihydro-5-methylene-2-phenylfuran
  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：

  苯甲酰乙腈 在 tetrabutylammonium tetrafluoroborate 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 1.0h， 生成 3-cyano-4,5-dihydro-2-phenyl-5-<(phenylseleno)methyl>furan
  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

• Phenylseleno-lactonization of olefinic nitriles promoted byperoxydisulphate ion oxidation of diphenyl diselenide
  作者：Marcello Tiecco、Lorenzo Testaferri、Marco Tingoli、Donatella Bartoli

  DOI：10.1016/s0040-4020(01)89150-x

  日期：1989.1

  The oxidation of diphenyl diselenide with ammonium peroxydisulphate is a very simple and efficient method to produce phenylselenium cations in the absence of nucleophilic counter ions. The reaction carried out in the presence of an olefin, in acetonitrile or propionitrile containing trifluoromethanesulphonic acid and water afforded the amidoselenenylation products in good yield. The intramolecular

  用过氧二硫酸铵氧化二苯二硒化物是一种在不存在亲核抗衡离子的情况下生产苯基硒阳离子的非常简单有效的方法。该反应在烯烃的存在下，在含有三氟甲磺酸和水的乙腈或丙腈中进行，以高收率得到了酰胺基亚硒基化产物。该反应的分子内形式，使用适当的不饱和腈作为起始产物，并以二恶烷为溶剂，采取了不同的路线，并以良好的收率得到了苯基硒代内酯。这种新的硒诱导的闭环反应通过羟基硒烯基化产物的初始形成而进行，其中羟基被认为是分子内协助氰基的水解。
• 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
• 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。
• 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.