(1S)-1-phenyl-2-(phenylseleno)ethanol | 223393-84-8

• 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: (1S)-1-phenyl-2-(phenylseleno)ethanol
• 英文别名: (1S)-1-phenyl-2-phenylselanylethanol
• CAS: 223393-84-8
• 化学式: C₁₄H₁₄OSe
• 分子量: 277.225
• InChiKey: RKLQIYWNDDRJHD-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.17
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  (1S)-1-phenyl-2-(phenylseleno)ethanol 在 sodium hydride 、 二异丁基氢化铝 作用下， 以 甲苯 、 苯 为溶剂， 生成 {[(1S)-1-phenyl-2-(phenylseleno)ethyl]oxy}acetaldehyde
  参考文献：
  名称：

  Intramolecular addition of carbon radicals to aldehydes: synthesis of enantiopure tetrahydrofuran-3-ols

  摘要：

  A simple and efficient substrate-controlled asymmetric synthesis of enantiopure tetrahydrofuran-3-ols by a 5-exo-trig radical cyclization is described. This cyclization occurs when a delta-carbon radical adds intramolecularly to the carbonyl group of an aldehyde. The delta-carbon radicals can be efficiently produced from the tin hydride mediated deselenenylation of 5-phenylseleno-3-oxapentanals, which were easily prepared starting from commercially available enantiopure epoxides or chlorohydrins. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.04.047
• 作为产物：
  描述：

  二苯基二硒醚 、 (S)-(+)-2-氯-1-苯乙醇 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 生成 (1S)-1-phenyl-2-(phenylseleno)ethanol
  参考文献：
  名称：

  Intramolecular addition of carbon radicals to aldehydes: synthesis of enantiopure tetrahydrofuran-3-ols

  摘要：

  A simple and efficient substrate-controlled asymmetric synthesis of enantiopure tetrahydrofuran-3-ols by a 5-exo-trig radical cyclization is described. This cyclization occurs when a delta-carbon radical adds intramolecularly to the carbonyl group of an aldehyde. The delta-carbon radicals can be efficiently produced from the tin hydride mediated deselenenylation of 5-phenylseleno-3-oxapentanals, which were easily prepared starting from commercially available enantiopure epoxides or chlorohydrins. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.04.047

文献信息

• Ring-Closure Reactions through Intramolecular Displacement of the Phenylselenonyl Group by Nitrogen Nucleophiles: A New Stereospecific Synthesis ofN-Tosyl andN-Benzoyl-1,3-oxazolidin-2-ones fromβ-Hydroxyalkyl Phenyl Selenides
  作者：Marcello Tiecco、Lorenzo Testaferri、Andrea Temperini、Luana Bagnoli、Francesca Marini、Claudio Santi

  DOI：10.1002/chem.200305497

  日期：2004.4.2

  3-oxazolidin-2-ones from the easily available beta-hydroxyalkyl phenyl selenides is presented. After transformation into the N-tosyl or N-benzoyl carbamates, the selenides were oxidized to the corresponding selenones. The key step of the process is the ring-closure reaction, which occurs by stereospecific intramolecular nucleophilic substitution of the selenone group by the nitrogen atom of the carbamate. Enantiomerically

  提出了一种新的方便的方法，用于从容易获得的β-羟烷基苯基硒化物立体定向合成各种取代的1,3-恶唑烷-2-酮。在转变成N-甲苯磺酰基或N-苯甲酰基氨基甲酸酯之后，硒化物被氧化成相应的硒酮。该过程的关键步骤是闭环反应，该反应是通过氨基甲酸酯的氮原子对硒酮基团进行立体特异性分子内亲核取代而发生的。通过使用对映体纯的β-羟烷基苯基硒化物作为起始原料，可以容易地制备对映体纯的1，3-恶唑烷-2-酮衍生物。
• The Enantioselective Chalcogeno-Baylis-Hillman Reaction Using a Chiral Hydroxy Chalcogenide-TiCl₄Complex
  作者：Tadashi Kataoka、Tetsuo Iwama、Shin-ichiro Tsujiyama、Kiyoko Kanematsu、Tatsunori Iwamura、Shin-ichi Watanabe

  DOI：10.1246/cl.1999.257

  日期：1999.3

  The enantioselective chalcogeno-Baylis-Hillman reaction was investigated by the use of chiral hydroxy chalcogenides in the presence of TiCl4 under atmospheric pressure. The best result was obtained with 10-methylthioisobornenol as a chiral hydroxy chalcogenide.

  在常压下，使用手性羟基钙苷在 TiCl4 的存在下研究了对映体选择性钙苷-Baylis-Hillman 反应。使用 10-甲硫基异冰片烯醇作为手性羟基卤化物获得了最佳结果。
• Synthesis of enantiomerically pure substituted tetrahydrofurans from epoxides and phenylselenium reagents
  作者：Marcello Tiecco、Lorenzo Testaferri、Luana Bagnoli、Valentina Purgatorio、Andrea Temperini、Francesca Marini、Claudio Santi

  DOI：10.1016/j.tetasy.2003.10.042

  日期：2004.2

  pure epoxides, enantiomerically pure substituted tetrahydrofurans were prepared using simple conversions promoted by organoselenium reagents. The first step consisted in the opening of the epoxides with phenylselenolate anions to afford hydroxyalkyl phenyl selenides. The PhSe group was then substituted by an allyl group by treatment with allyltributyltin and AIBN. The reaction of these allylic derivatives

  从市售对映体纯的环氧化物开始，使用有机硒试剂促进的简单转化制备对映体纯的取代的四氢呋喃。第一步是用苯硒酸根阴离子打开环氧化物，得到羟烷基苯基硒化物。然后通过用烯丙基三丁基锡和AIBN处理将PhSe基团用烯丙基取代。这些烯丙基衍生物与亲电试剂phenylselenium反应得到的含有硒的四氢呋喃作为立体特异性5-的结果外切- trig的环化。最终将由此获得的四氢呋喃衍生物用氢化三苯锡和AIBN进行去硒烯基化。
• Lipase-catalyzed resolution of β-hydroxy selenides
  作者：Michelangelo Gruttadauria、Paolo Lo Meo、Serena Riela、Francesca D’Anna、Renato Noto

  DOI：10.1016/j.tetasy.2006.10.010

  日期：2006.10

  Eleven beta-hydroxy selenides were kinetically resolved using an immobilized lipase (Amano PS-C II) in toluene in the presence of vinyl acetate at 30 degrees C. This approach provided, in several cases, both enantiomers in high enantiomeric excess. The role of the size of substituents and the behaviour of cyclic beta-hydroxy selenides is also discussed. Enantiopure beta-hydroxy selenides are useful building blocks. As an application of this chemistry, enantiopure (1S,2R)-indene oxide was obtained in one step from the proper enantiopure beta-hydroxy selenide. (c) 2006 Published by Elsevier Ltd.