2-羟基-3-苯基丙基苯基硒化物 | 68395-97-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-羟基-3-苯基丙基苯基硒化物
• 英文名称: 2-hydroxy-3-phenylpropyl phenyl selenide
• 英文别名: 1-phenyl-3-(phenylselanyl)propan-2-ol；1-Phenyl-3-phenylselanylpropan-2-ol
• CAS: 68395-97-1
• 化学式: C₁₅H₁₆OSe
• 分子量: 291.251
• InChiKey: MJQPCUHPDDGMTL-UHFFFAOYSA-N

物化性质

• 沸点：
  412.0±45.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.04
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-羟基-3-苯基丙基苯基硒化物 在 偶氮二异丁腈 、 三(三甲基硅基)硅烷 、 sodium hydride 作用下， 以 四氢呋喃 、 苯 为溶剂， 20.0~80.0 ℃ 、8.11 MPa 条件下， 反应 6.25h， 生成 (2R*,5S*)-2-benzenesulfonylmethyl-5-benzyl-dihydro-furan-3-one
  参考文献：
  名称：

  Construction of Tetrahydrofuran-3-ones from Readily Available Organochalcogen Precursors via Radical Carbonylation/Reductive Cyclization

  摘要：

  [GRAPHICS]b-Hydroxyalkyl aryl chalcogenides, readily available by regioselective ring-opening of epoxides with nucleophilic benzeneselenolate or tellurolate, were O-alkylated by treatment with ethyl propiolate or (E)-1,2-bis(phenylsulfonyl)ethylene. Subsequent carbonylation/reductive cyclization in the presence of AIBN/TTMSS and carbon monoxide (80 atm) afforded tetrahydrofuran-3-ones in moderate to good yields.

  DOI：

  10.1021/ol016127q
• 作为产物：
  描述：

  二苯基二硒醚 在 盐酸 、 sodium tetrahydroborate 、 potassium hydroxide 作用下， 以 乙醇 、 水 、 乙酸乙酯 为溶剂， 反应 33.5h， 生成 2-羟基-3-苯基丙基苯基硒化物
  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

• Oxidation of Diphenyl Diselenide with 2,3-Dichloro-5,6-dicyanobenzoquinone (DDQ). A New Method for the Electrophilic Phenylselenenylation of Alkenes under Mild Conditions
  作者：Marcello Tiecco、Lorenzo Testaferri、Andrea Temperini、Luana Bagnoli、Francesca Marini、Claudio Santi

  DOI：10.1055/s-2001-18091

  日期：——

  The oxidation of diphenyl diselenide with 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) represents a convenient mild method to produce a strongly electrophilic phenylselenium reagent. Clean phenylseleno methoxylations and hydroxylations of alkenes containing different types of functional groups can be effected by working in methanol or in acetonitrile and water, respectively. This new electrophilic reagent can also be employed to promote efficient cyclization reactions of alkenols to tetrahydrofurans or of alkenoic acids to lactones.

  二苯二硒化物与2,3-二氯-5,6-二氰苯醌（DDQ）的氧化反应是一种方便温和的方法，可以生成强亲电子性的苯基硒试剂。在甲醇或乙腈和水的条件下，可以对含有不同类型官能团的烯烃进行干净的苯基硒醚化和羟基化。这种新的亲电子试剂还可以用于促进烯醇向四氢呋喃或烯酸向内酯的高效环化反应。
• Facile One‐Pot Synthesis of Oxazolidin‐2‐ones from Phenyl 2‐Hydroxyalkyl Selenides
  作者：Shou‐Ri Sheng、Hai‐Rong Luo、Zhen‐Zhong Huang、Wu‐Kang Sun、Xiao‐Ling Liu

  DOI：10.1080/00397910701465420

  日期：2007.8

  Abstract A novel, convenient, efficient, three‐step, one‐pot synthesis of 2‐oxazolidinones from phenyl 2‐hydroxyalkyl selenides was developed. Using this methodology, 2‐oxazolidinones are obtained in good yields (76–85%) by reaction of phenyl 2‐hydroxyalkyl selenides with benzoyl isocyanate and subsequent oxidation/cyclization, followed by hydrolysis with hydrochloric acid solution.

  摘要 开发了一种新颖、方便、高效、三步、一锅法从苯基 2-羟烷基硒化物合成 2-恶唑烷酮的方法。使用这种方法，通过苯基 2-羟烷基硒化物与异氰酸苯甲酰酯反应，随后氧化/环化，然后用盐酸溶液水解，以良好的收率（76-85%）获得 2-恶唑烷酮。
• NMR chiral discrimination of chalcogen containing secondary alcohols
  作者：Naiade B.G. Marques、Raquel G. Jacob、Gelson Perin、Eder J. Lenardão、Diego Alves、Márcio S. Silva

  DOI：10.1002/chir.23030

  日期：2019.1

  stable, nonhygroscopic, and readily available chiral derivatizing agent (CDA) for NMR chiral discrimination of chalcogen containing secondary alcohols. The chiral recognition by CDA and chiral solvating agent (CSA) was assessed using 1H, 77Se‐1H}, and 125Te‐1H} NMR spectroscopy. A simple model for the assignment of the absolute configuration from NMR data is presented.

  在这里，我们报告了可以使用NMR光谱法确定含硫属元素的仲醇的对映体纯度和绝对构型的一般策略，包括使用手性溶剂化和手性衍生剂的评估。BINOL / DMAP三元复合物证明了测定对映体纯度的简单而快速的协议。萘普生药物提供了一种稳定，不吸湿且易于获得的手性衍生剂（CDA），用于对含硫族元素的仲醇进行NMR手性鉴别。使用1 H，77 Se- 1H}和125 H评估CDA和手性溶剂化剂（CSA）的手性识别Te- 1H} NMR光谱。提供了一个简单的模型，用于根据NMR数据分配绝对构型。
• Radical Carbonylation/Reductive Cyclization for the Construction of Tetrahydrofuran-3-ones and Pyrrolidin-3-ones
  作者：Stefan Berlin、Cecilia Ericsson、Lars Engman

  DOI：10.1021/jo030153f

  日期：2003.10.1

  beta-Hydroxyalkyl aryl chalcogenides obtained by regioselective ring-opening of epoxides with benzeneselenolate or -tellurolate were found to undergo efficient hetero-Michael addition when treated with ethyl propiolate. Subsequent carbonylation/reductive cyclization of the resulting vinylogous carbonates in the presence of AIBN/TTMSS and carbon monoxide (80 atm) afforded 2,5-disubstituted tetrahydrofuran-3-ones, predominantly as cis isomers (cis/trans = 4/1-9/1). Starting from a polymer-supported diaryl diselenide, the methodology was also successfully extended to solid-phase synthesis. Vinylogous carbamates prepared by hetero-Michael addition of aziridines to electron-deficient alkynes were regioselectively ring-opened with benzeneselenolate from the sterically least hindered side. Radical carbonylation/reductive cyclization of the resulting N-vinyl-beta-amino-alkyl phenyl selenides afforded 2,5-disubstituted pyrrolidin-3-ones, predominantly as cis isomers (cis/trans = 3/1-12/1).
• 10.3998/ark.5550190.p009.906
  作者：Borges, Elton L.、Jacob, Raquel G.、Lenardão, Eder J.、Lima, David B.、Perin, Gelson、Silva, Márcio S.、Silva, Patrícia C.

  DOI：10.3998/ark.5550190.p009.906

  日期：——