(2R)-3-(phenylseleno)propane-1,2-diol | 744198-92-3

• 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: (2R)-3-(phenylseleno)propane-1,2-diol
• 英文别名: (2R)-3-phenylselanylpropane-1,2-diol
• CAS: 744198-92-3
• 化学式: C₉H₁₂O₂Se
• 分子量: 231.153
• InChiKey: WSKDWDWIFRMWQD-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.21
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R)-3-(phenylseleno)propane-1,2-diol 在 咪唑 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 5.0h， 生成 methyl ({(1R)-2-{[tert-butyl(diphenyl)silyl]oxy}-1-[(phenylseleno)methyl]ethyl}oxy)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：

  二苯基二硒醚 、 (R)-缩水甘油 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 6.5h， 以93%的产率得到(2R)-3-(phenylseleno)propane-1,2-diol
  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。
• 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.