2-hydroxy-3-phenylpropyl phenyl telluride | 396714-79-7

• 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: 2-hydroxy-3-phenylpropyl phenyl telluride
• 英文别名: 1-phenyl-3-(phenyltellanyl)propan-2-ol；1-Phenyl-3-phenyltellanylpropan-2-ol
• CAS: 396714-79-7
• 化学式: C₁₅H₁₆OTe
• 分子量: 339.891
• InChiKey: IWOTYQNKQZWEDM-UHFFFAOYSA-N

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-hydroxy-3-phenylpropyl phenyl telluride 在 sodium hydride 作用下， 以 四氢呋喃 、 乙二醇 为溶剂， 反应 0.1h， 生成 cis-2-benzyl-4-[(phenyltelluro)methyl]tetrahydrofuran
  参考文献：
  名称：

  Microwave-Assisted Group-Transfer Cyclization of Organotellurium Compounds

  摘要：

  Primary- and secondary-alkyl aryl tellurides, prepared by arenetellurolate ring-opening of epoxides/O-allylation, were found to undergo rapid (3 - 10 min) group-transfer cyclization to afford tetrahydrofuran derivatives in 60-74% yield when heated in a microwave cavity at 250 degreesC in ethylene glycol or at 180 degreesC in water. To go to completion, similar transformations had previously required extended photolysis in refluxing benzene containing a substantial amount of hexabutylditin. The only drawback of the microwave-assisted process was the loss in diastereoselectivity which is a consequence of the higher reaction temperature. Substitution in the Te-aryl moiety of the secondary-alkyl aryl tellurides (4-OMe, 4-H, 4-CF3) did not affect the outcome of the group-transfer reaction in ethylene glycol. However, at lower temperature, using water as a solvent, the CF3 derivative failed to react. The microwave-assisted group-transfer cyclization was extended to benzylic but not to primary- and secondary-alkyl phenyl selenides.

  DOI：

  10.1021/jo040155f
• 作为产物：
  描述：

  (2,3-环氧丙基)苯 、 联苯二碲 在 aluminum oxide 、 sodium tetrahydroborate 作用下， 反应 2.0h， 以77%的产率得到2-hydroxy-3-phenylpropyl phenyl telluride
  参考文献：
  名称：

  含硫属元素的仲醇的NMR手性鉴别。

  摘要：

  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。

  DOI：

  10.1002/chir.23030

文献信息

• 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：——
• Construction of Tetrahydrofuran-3-ones from Readily Available Organochalcogen Precursors via Radical Carbonylation/Reductive Cyclization
  作者：Stefan Berlin、Cecilia Ericsson、Lars Engman

  DOI：10.1021/ol016127q

  日期：2002.1.1

  [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.
• 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。
• Microwave-Assisted Group-Transfer Cyclization of Organotellurium Compounds
  作者：Cecilia Ericsson、Lars Engman

  DOI：10.1021/jo040155f

  日期：2004.7.1

  Primary- and secondary-alkyl aryl tellurides, prepared by arenetellurolate ring-opening of epoxides/O-allylation, were found to undergo rapid (3 - 10 min) group-transfer cyclization to afford tetrahydrofuran derivatives in 60-74% yield when heated in a microwave cavity at 250 degreesC in ethylene glycol or at 180 degreesC in water. To go to completion, similar transformations had previously required extended photolysis in refluxing benzene containing a substantial amount of hexabutylditin. The only drawback of the microwave-assisted process was the loss in diastereoselectivity which is a consequence of the higher reaction temperature. Substitution in the Te-aryl moiety of the secondary-alkyl aryl tellurides (4-OMe, 4-H, 4-CF3) did not affect the outcome of the group-transfer reaction in ethylene glycol. However, at lower temperature, using water as a solvent, the CF3 derivative failed to react. The microwave-assisted group-transfer cyclization was extended to benzylic but not to primary- and secondary-alkyl phenyl selenides.