Methyl (Z)-3-phenylselenoacrylate | 15642-77-0

• 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 (Z)-3-phenylselenoacrylate
• 英文别名: methyl 3-(phenylseleno)acrylate；cis-3-Phenylseleno-acrylsaeure-methylester；methyl (Z)-3-phenylselanylprop-2-enoate
• CAS: 15642-77-0
• 化学式: C₁₀H₁₀O₂Se
• 分子量: 241.148
• InChiKey: CNXFTZQUFGKZBG-FPLPWBNLSA-N

物化性质

• 沸点：
  295.6±32.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  二苯基二硒醚 在 盐酸 、 sodium tetrahydroborate 、 碳酸氢钠 作用下， 以 乙醇 、 水 、 乙酸乙酯 为溶剂， 反应 46.5h， 生成 Methyl (Z)-3-phenylselenoacrylate
  参考文献：
  名称：

  O-(tert-butyl) Se-phenyl selenocarbonate: A convenient, bench-stable and metal-free precursor of benzeneselenol

  摘要：

  A study by our laboratory shows that air, light and moisture stable O-(tert-butyl) Se-phenyl selenocarbonate could be employed as a safer, practical and efficient alternative to generate "in situ" benzeneselenol or benzeneselenolate anion under different and transition metal-free conditions. This procedure seems to be of general application since the nucleophilic selenium species obtained can be trapped by electrophiles such as alkyl halides, epoxides and electron-deficient alkenes and alkynes under different reaction conditions. (C) 2020 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2020.131311

文献信息

• Chemoselective and metal-free reduction of α,β-unsaturated ketones by <i>in situ</i> produced benzeneselenol from <i>O</i>-(<i>tert</i>-butyl) Se-phenyl selenocarbonate
  作者：Andrea Temperini、Marco Ballarotto、Carlo Siciliano

  DOI：10.1039/d0ra07128e

  日期：——

  The carbon–carbon double bond of arylidene acetones and chalcones can be selectively reduced with benzeneselenol generated in situ by reacting O-(tert-butyl) Se-phenyl selenocarbonate with hydrochloric acid in ethanol. This mild, metal-free and experimentally simple reduction procedure displays considerable functional-group compatibility, products are obtained in good to excellent yields, and the use

  亚芳基丙酮和查耳酮的碳碳双键可以通过O- (叔丁基)硒苯基硒代碳酸酯与盐酸在乙醇中的反应原位产生的苯硒醇选择性还原。这种温和、无金属且实验简单的还原过程显示出相当大的官能团兼容性，产品的收率非常好，并且避免使用有毒的 Se/CO 混合物和 NaSeH，或有气味且对空气敏感的苯硒醇.
• Palladium and platinum catalyzed hydroselenation of alkynes: SeH vs SeSe addition to CC bond
  作者：Valentine P Ananikov、Denis A Malyshev、Irina P Beletskaya、Grigory G Aleksandrov、Igor L Eremenko

  DOI：10.1016/s0022-328x(03)00546-1

  日期：2003.8

  alkynes catalyzed by Pd(PPh3)4 and Pt(PPh3)4 has shown that the palladium complex gives products of both SeH and SeSe bond addition to the triple bond of alkynes, while the platinum complex selectively catalyzes SeH bond addition. The key intermediate of PhSeH addition to the metal center, namely Pt(H)(SePh)(PPh3)2, was detected by 1H-NMR spectroscopy. The analogous palladium complex rapidly decomposes

  对Pd（PPh 3）4和Pt（PPh 3）4催化的炔烃加氢精制的机理研究表明，钯配合物使SeH和SeSe键的产物加成到炔烃的三键上，而铂络合物选择性催化SeH键的添加。通过1 H-NMR光谱检测到PhSeH添加到金属中心的关键中间体，即Pt（H）（SePh）（PPh 3）2。类似的钯配合物随着分子氢的释放而迅速分解。开发了一种方便的方法来制备马尔可夫尼可夫盐精制产物H 2CC（SePh）R，并研究了该反应的范围。的马氏产物H的第一X射线结构2 CC（SEPH）CH 2 Ñ + HME 2 ·HOOCCOO -报道。
• Vinyl radical generation with selenoborane and its application to cyclization reaction of enynes
  作者：Tadashi Kataoka、Mitsuhiro Yoshimatsu、Hiroshi Shimizu、Mikio Hori

  DOI：10.1016/s0040-4039(00)97996-6

  日期：1990.1

  Tris(methylseleno)- and tris(phenylseleno)boranes added to acetylenes to afford methylseleno- and phenylseleno-substituted -vinylselenides in high yields. The addition reactions proceeded by way of free radicals and were applied to cyclization reactions of enyne compounds. The radical cyclization provided pyrrolidine derivatives diastereoselectively.

  将三（甲基硒代）-和三（苯基硒代）硼烷加到乙炔中，以高收率得到甲基硒代和苯基硒代取代的乙烯基硒化物。加成反应通过自由基进行，并用于烯炔化合物的环化反应。自由基环化非对映选择性地提供了吡咯烷衍生物。
• “On-Water” Michael-Type Addition Reactions Promoted by PhSeZnCl
  作者：Benedetta Battistelli、Testaferri Lorenzo、Marcello Tiecco、Claudio Santi

  DOI：10.1002/ejoc.201100045

  日期：2011.4

  communication we report that our reagent PhSeZnCl can be conveniently used to effect Michael addition like reactions of unsaturated ketones and electron-deficient alkynes, leading to synthetically useful β-seleno derivatives and vinyl selenides, respectively. The reactions are effected at room temperature in THF as well as under "on water" conditions. When the addition occurs on a triple bond, good stereoselectivity

  在这篇通讯中，我们报告说我们的试剂 PhSeZnCl 可以方便地用于影响不饱和酮和缺电子炔烃的迈克尔加成反应，分别导致合成有用的 β-硒代衍生物和乙烯基硒化物。反应在室温下在 THF 中以及在“水上”条件下进行。当加成发生在三键上时，观察到良好的立体选择性，并且反应在水悬浮液中显示出速率加速。
• ——
  作者：V. P. Ananikov、D. A. Malyshev、I. P. Beletskaya

  DOI：10.1023/a:1022500420741

  日期：——

  Addition of benzeneselenol to terminal alkynes HCdropCR, catalyzed by Pd(0) complexes, leads to formation of mixtures of mono- and bis(phenylseleno)alkenes, depending on the nature of the R substituent. Electron-donor groups (R = Bu, CH2OH, CH2NMe2) give rise to addition according to the Markownikoff rule, whereas from alkynes with electron-acceptor groups (R = Ph, COOMe) mixtures of products are formed as a result of side reactions. A probable reaction mechanism includes oxidative addition of benzeneselenol to the metal, alkyne insertion into the Pd-Se bond, and reductive elimination.