2-hydroxy-3-phenoxypropyl phenyl telluride | 743420-48-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-hydroxy-3-phenoxypropyl phenyl telluride
• 英文别名: 1-phenoxy-3-(phenyltellanyl)propan-2-ol；1-Phenoxy-3-phenyltellanylpropan-2-ol
• CAS: 743420-48-6
• 化学式: C₁₅H₁₆O₂Te
• 分子量: 355.891
• InChiKey: PDCYBVGTJWCXGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.87
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-hydroxy-3-phenoxypropyl 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 trans-2-phenoxymethyl-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：

  联苯二碲 、 苯基缩水甘油醚 在 aluminum oxide 、 sodium tetrahydroborate 作用下， 反应 2.0h， 以82%的产率得到2-hydroxy-3-phenoxypropyl 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

• Rongalite Promoted Highly Regioselective Synthesis of <i>β</i>-hydroxytellurides
  作者：Dongsheng Sui、Feifei Wu、Qing Xu、Xiaochun Yu

  DOI：10.3184/174751911x13049538828959

  日期：2011.5

  Ditellurides undergo facile cleavage on treatment with rongalite (sodium hydroxymethanesulfinate) to generate tellurium anions in situ, which undergo ring opening of epoxides in high regioselective manner. A simple, cost-effective method has been developed to prepare β-hydroxytellurides with good yields.

  双碲化物在用 rongalite（羟基甲亚磺酸钠）处理时容易裂解，原位生成碲阴离子，以高区域选择性方式使环氧化物开环。已经开发出一种简单、经济高效的方法来制备具有良好产率的 β-羟基碲化物。
• 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：——
• 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.