2,3-dihydro-2-<(phenylseleno)methyl>benzofuran | 66558-11-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: 2,3-dihydro-2-<(phenylseleno)methyl>benzofuran
• 英文别名: 2-((phenylselanyl)methyl)-2,3-dihydrobenzofuran；2-(phenylselenomethyl)-2,3-dihydrobenzofuran；2-phenylselenomethyl-2,3-dihydrobenzofuran；2-(phenylselanyl-methyl)-2,3-dihydro-benzofuran；2-(Phenylselanylmethyl)-2,3-dihydro-1-benzofuran
• CAS: 66558-11-0
• 化学式: C₁₅H₁₄OSe
• 分子量: 289.236
• InChiKey: BDXKISVTHDWTFF-UHFFFAOYSA-N

物化性质

• 熔点：
  61-62 °C(Solv: ligroine (8032-32-4))
• 沸点：
  390.7±25.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.44
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,3-dihydro-2-<(phenylseleno)methyl>benzofuran 在 双氧水 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成
  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：

  苯基氯化硒 、 2-烯丙基酚 以 二氯甲烷 为溶剂， 以82%的产率得到2,3-dihydro-2-<(phenylseleno)methyl>benzofuran
  参考文献：
  名称：

  从 2-烯基苯胺和活性硒合成吲哚、3,1-苯并恶嗪和喹啉

  摘要：

  二苯基二硒化物与[双(三氟乙酰氧基)碘]苯反应，然后加入2-烯丙基苯酚，以82%的产率得到2-苯基硒基甲基-2,3-二氢-苯并呋喃。苯硒酰氯与 N-tosyl-2-isopropenylanilide 反应，然后加入 m-CPBA，以 68% 的产率得到 N-tosyl-3-methylindole。有趣的是，二苯基二硒化物与 [双（三氟乙酰氧基）碘] 苯反应，然后加入 2-异丙烯基苯胺，以 65% 的产率得到 4-甲基-4-苯基硒甲基-2-三氟甲基-3,1-苯并恶嗪。

  DOI：

  10.1080/10426501003772169

文献信息

• Organoselenium-induced cyclizations in organic synthesis
  作者：K.C. Nicolaou

  DOI：10.1016/s0040-4020(01)93285-5

  日期：——

  A number of organoselenium reagents are introduced as efficient initiators of ring closures leading from unsaturated substrates to lactones, cyclic ethers, cyclic thioethers, N-heterocycles and carbocycles. These cyclizations often proceed with high ring selectivity and stereoselectivity and are accompanied by the incorporation of the phenylseleno group (PhSe) into the final product. Methods are described

  引入了许多有机硒试剂，作为从不饱和底物到内酯，环醚，环硫醚，N-杂环和碳环的有效的环闭合引发剂。这些环化通常以高环选择性和立体选择性进行，并伴随有苯硒基（PhSe）结合到最终产物中。描述了通过氧化或还原以实现不饱和或饱和来有效去除该基团（PhSe）的方法。最后，概述了这种基于硒的方法在稳定和具有生物活性的前列环素的合成中的成功应用。包括代表性的实验程序。
• 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。
• A mild and efficient procedure for alkenols oxyselenocyclization by using ionic liquids
  作者：Marina Kostić、Pedro Verdía、Verónica Fernández‐Stefanuto、Ralph Puchta、Emilia Tojo

  DOI：10.1002/poc.3928

  日期：2019.5

  treatment with phenylselenyl chloride using ionic liquids as solvents/catalyzers has been developed. The reaction proceeds instantaneously under mild conditions with absolute regioselectivity, using primary, secondary, tertiary, and aromatic alcohols, as well as monosubstituted, disubstituted, and trisubstituted alkenols. This procedure provides a new method for the synthesis of substituted tetrahydrofurans

  通过使用离子液体作为溶剂/催化剂，用苯硒基氯进行处理，开发了一种温和而有效的不饱和醇的氧硒环化方法。使用伯，仲，叔和芳族醇，以及单取代，二取代和三取代的烯醇，该反应在温和条件下以绝对的区域选择性瞬时进行。该方法为合成取代的四氢呋喃和四氢吡喃醚（许多具有生物活性的代谢物的前体）提供了一种新方法，从而避免了使用有毒和腐蚀性的催化剂。以前没有离子液体中硒介导的环功能化反应的报道。考虑到[MMIM] [MSO 4 ]的良好结果其易于制备，低粘度，低价格，可回收再利用的能力被选作溶剂/催化剂。量子化学计算（MP2（fc）/ 6-311 + G ** // B3LYP / 6-311 + G **）表明，分子内环化是由离子液体阴离子与羟基之间形成的氢键促进的组烯醇。
• Electrochemical synthesis of selenyl-dihydrofurans <i>via</i> anodic selenofunctionalization of allyl-naphthol/phenol derivatives and their anti-Alzheimer activity
  作者：Marcos R. Scheide、Alex R. Schneider、Guilherme A. M. Jardim、Guilherme M. Martins、Daniele C. Durigon、Sumbal Saba、Jamal Rafique、Antonio L. Braga

  DOI：10.1039/d0ob00629g

  日期：——

  Herein, we report an eco-friendly, electrosynthetic approach for the intramolecular oxyselenylation of allyl-naphthol/phenol derivatives. This reaction proceeds with 0.2 equiv. of nBu4NClO4 as an electrolyte and Pt working electrodes in an undivided cell, resulting in the selenyl-dihydrofurans in good to excellent yields. Furthermore, several of the synthesized products presented a high percentage

  在此，我们报告了烯丙基萘酚/苯酚衍生物的分子内氧硒化反应的生态友好型电合成方法。该反应以0.2当量进行。在一个未分开的电池中，将n Bu 4 NClO 4用作电解质和Pt工作电极，得到的硒基二氢呋喃具有良好至极好的产率。此外，一些合成产物表现出高百分比的乙酰胆碱酯酶（AChE）抑制作用，突出了其潜在的抗阿尔茨海默氏病活性。
• Green Approach for the Synthesis of Chalcogenyl‐ 2,3‐dihydrobenzofuran Derivatives Through Allyl‐phenols/ Naphthols and Their Potential as MAO‐B Inhibitors
  作者：Amanda R. Azevedo、Pâmella Cordeiro、Dianer N. Strelow、Karine N. de Andrade、Marcos R. S. Neto、Rodolfo Goetze Fiorot、César A. Brüning、Antonio L. Braga、Luciano M. Lião、Cristiani F. Bortolatto、José S. S. Neto、Vanessa Nascimento

  DOI：10.1002/asia.202300586

  日期：2023.12.14

  This study focuses on the design, synthesis, and activity of chalcogenyl-2,3-dihydrobenzofuran derivatives as MAO-B inhibitors. A series of chalcogen-containing dihydrobenzofurans were successfully synthesized using a solvent- and metal-free approach with high yields. The proposed mechanism involving iodide species was investigated through theoretical calculations. Promising MAO-B inhibitory activity

  本研究重点关注硫属基-2,3-二氢苯并呋喃衍生物作为 MAO-B 抑制剂的设计、合成和活性。采用无溶剂和无金属的方法成功合成了一系列含硫族二氢苯并呋喃，且收率高。通过理论计算研究了涉及碘化物物质的所提出的机制。一些合成的化合物观察到了良好的 MAO-B 抑制活性。