(1R)-1-phenyl-2-(phenylseleno)ethanol | 204574-76-5

• 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: (1R)-1-phenyl-2-(phenylseleno)ethanol
• 英文别名: (1R)-1-phenyl-2-phenylselanylethanol
• CAS: 204574-76-5
• 化学式: C₁₄H₁₄OSe
• 分子量: 277.225
• InChiKey: RKLQIYWNDDRJHD-AWEZNQCLSA-N

物化性质

• 沸点：
  400.167±45.00 °C(Press: 760.00 Torr)(predicted)

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：

  (1R)-1-phenyl-2-(phenylseleno)ethanol 在 吡啶 、 偶氮二异丁腈 、 三正丁基氢锡 、 sodium hydride 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 甲苯 、 苯 为溶剂， 生成 (3R,5S)-5-phenyltetrahydrofuran-3-yl acetate
  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：

  α-(phenylseleno)acetophenone 在 甲酸 、 [(1S,2S)-N-(p-toluensulfonyl)-1,2-diphenylethanediamine](p-cymene)ruthenium (I) 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以95 %的产率得到(1R)-1-phenyl-2-(phenylseleno)ethanol
  参考文献：
  名称：

  CN116178232

  摘要：

  公开号：

文献信息

• Mechanistic Course of the Asymmetric Methoxyselenenylation Reaction
  作者：Thomas Wirth、Gianfranco Fragale、Martin Spichty

  DOI：10.1021/ja974177d

  日期：1998.4.1

  competition experiments it was shown that the formation of these intermediates is reversible. The seleniranium ions of type 20 + formed by addition of chiral selenium electrophiles to alkenes are the decisive intermediates in the asymmetric methoxyselenenylation reaction. Their stabilities are strongly dependent on the strength of the selenium-heteroatom interaction. This was shown experimentally, because

  在烯烃的烷氧基硒基化反应中，形成中间体硒离子 1。在竞争实验中表明这些中间体的形成是可逆的。通过将手性硒亲电子试剂加成到烯烃上形成的 20 + 型硒离子是不对称甲氧基硒基化反应中的决定性中间体。它们的稳定性强烈依赖于硒-杂原子相互作用的强度。这是通过实验证明的，因为已经使用了一种独立的方法来合成不同的非对映硒离子。此外，还进行了计算以确定非对映体硒离子 20 + 的相对稳定性。从计算中获得的结果支持了实验结果。
• Stereospecific carbon–carbon bond formation by the reaction of a chiral episelenonium ion with aromatic compounds
  作者：Kazuki Okamoto、Yoshiaki Nishibayashi、Sakae Uemura、Akio Toshimitsu

  DOI：10.1016/j.tetlet.2004.06.042

  日期：2004.8

  The stereospecific exchange of a hydroxyl group of chiral alcohols bearing a pyridylseleno group on the adjacent carbon atom with aromatic compounds occurred smoothly in the presence of Lewis acid.

  在路易斯酸的存在下，在相邻碳原子上带有吡啶基硒烯基的手性醇的羟基与芳族化合物的立体定向交换是平稳进行的。
• 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.
• Intramolecular addition of carbon radicals to aldehydes: synthesis of enantiopure tetrahydrofuran-3-ols
  作者：Marcello Tiecco、Lorenzo Testaferri、Francesca Marini、Silvia Sternativo、Claudio Santi、Luana Bagnoli、Andrea Temperini

  DOI：10.1016/j.tet.2007.04.047

  日期：2007.6

  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.