methyl 2-methyl-5-((phenylselanyl)methyl)-4,5-dihydrofuran-3-carboxylate | 123883-75-0

• 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: methyl 2-methyl-5-((phenylselanyl)methyl)-4,5-dihydrofuran-3-carboxylate
• 英文别名: methyl 5-methyl-2-(phenylselanylmethyl)-2,3-dihydrofuran-4-carboxylate
• CAS: 123883-75-0
• 化学式: C₁₄H₁₆O₃Se
• 分子量: 311.239
• InChiKey: WUAGTTTZFBPHLZ-UHFFFAOYSA-N

物化性质

• 沸点：
  388.5±42.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.67
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methyl 2-methyl-5-((phenylselanyl)methyl)-4,5-dihydrofuran-3-carboxylate 在 双氧水 、 碳酸氢钠 作用下， 以 甲醇 、 苯 为溶剂， 反应 22.0h， 生成 甲基2-甲基-5-亚甲基-4,5-二氢-3-呋喃羧酸酯
  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：

  乙酰乙酸甲酯 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 methyl 2-methyl-5-((phenylselanyl)methyl)-4,5-dihydrofuran-3-carboxylate
  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

• 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]。
• 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。
• 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