p-Methoxybenzyl 2,4,6-triisopropylphenyl selenide | 139706-17-5

• 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: p-Methoxybenzyl 2,4,6-triisopropylphenyl selenide
• 英文别名: 2-[(4-Methoxyphenyl)methylselanyl]-1,3,5-tri(propan-2-yl)benzene
• CAS: 139706-17-5
• 化学式: C₂₃H₃₂OSe
• 分子量: 403.466
• InChiKey: RPQOZYGXNQQHBW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  p-Methoxybenzyl 2,4,6-triisopropylphenyl selenide 在 (-)-N-(phenylsulfonyl)-(3,3-dichlorocamphoryl)oxaziridine 作用下， 以 氯仿 为溶剂， 反应 2.0h， 生成 (S)-(-)-p-Methoxybenzyl 2,4,6-triisopropylphenyl selenoxide 、 (S)-(-)-p-Methoxybenzyl 2,4,6-triisopropylphenyl selenoxide
  参考文献：
  名称：

  Asymmetric oxidation of simple selenides to selenoxides in high enantiopurity. Stereochemical aspects of the allyl selenoxide/allyl selenenate rearrangement

  摘要：

  For the first time simple alkyl aryl selenoxides of high enantiomeric purity (90-95% ee) and well-defined stereochemistry are available via the asymmetric oxidation of selenides using (+)- or (-)-N-(phenylsulfonyl)-(3,3-dichlorocamphoryl)oxaziridine [4, [3,3-dichloro-1,7,7-trimethyl-2'-(phenylsulfonyl)spiro[bicyclo[2.2.1]heptane-2,3'-oxaziridine]]]. These nonracemic selenoxides, which are more stable in solution than in the solid state, exhibit high configurational stability as long as acid and moisture are excluded. Complete racemization occurs within minutes on addition of trace amounts of acid and water. The asymmetric oxidation of (E)- and (Z)-aryl cinnamyl selenides 11 and 12 with oxaziridine (+)-4 affords optically active 1-phenyl allyl alcohol (15) via a concerted [2,3] sigmatropic selenoxide-selenenate rearrangement. The extent of 1 --> 3 chirality transfer (41-62% ee) as well as the endo/exo transition state geometry is highly dependent on the structure of the allylic selenide.

  DOI：

  10.1021/jo00035a014
• 作为产物：
  描述：

  bis(2,4,6-triisopropylphenyl)diselenide 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium tetrahydroborate 作用下， 生成 p-Methoxybenzyl 2,4,6-triisopropylphenyl selenide
  参考文献：
  名称：

  Asymmetric oxidation of simple selenides to selenoxides in high enantiopurity. Stereochemical aspects of the allyl selenoxide/allyl selenenate rearrangement

  摘要：

  For the first time simple alkyl aryl selenoxides of high enantiomeric purity (90-95% ee) and well-defined stereochemistry are available via the asymmetric oxidation of selenides using (+)- or (-)-N-(phenylsulfonyl)-(3,3-dichlorocamphoryl)oxaziridine [4, [3,3-dichloro-1,7,7-trimethyl-2'-(phenylsulfonyl)spiro[bicyclo[2.2.1]heptane-2,3'-oxaziridine]]]. These nonracemic selenoxides, which are more stable in solution than in the solid state, exhibit high configurational stability as long as acid and moisture are excluded. Complete racemization occurs within minutes on addition of trace amounts of acid and water. The asymmetric oxidation of (E)- and (Z)-aryl cinnamyl selenides 11 and 12 with oxaziridine (+)-4 affords optically active 1-phenyl allyl alcohol (15) via a concerted [2,3] sigmatropic selenoxide-selenenate rearrangement. The extent of 1 --> 3 chirality transfer (41-62% ee) as well as the endo/exo transition state geometry is highly dependent on the structure of the allylic selenide.

  DOI：

  10.1021/jo00035a014