benzyl (R)-4-hydroxy-3-(phenylselanyl)butanoate | 1428668-65-8

• 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: benzyl (R)-4-hydroxy-3-(phenylselanyl)butanoate
• 英文别名: benzyl (3R)-4-hydroxy-3-phenylselanylbutanoate
• CAS: 1428668-65-8
• 化学式: C₁₇H₁₈O₃Se
• 分子量: 349.288
• InChiKey: NSZNZBAHRKFJCQ-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.93
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  二苯基二硒醚 、 4-氧代丁酸苄酯 在 (R)-5-benzyl-2,2,3-trimethylimidazolidin-4-one 、 碘苯二乙酸 、 对硝基苯甲酸 、 甲醇 、 sodium tetrahydroborate 作用下， 以 甲苯 为溶剂， 反应 20.0h， 以70%的产率得到benzyl (R)-4-hydroxy-3-(phenylselanyl)butanoate
  参考文献：
  名称：

  Highly enantioselective organocatalytic α-selenylation of aldehydes using hypervalent iodine compounds

  摘要：

  The highly enantioselective organocatalytic alpha-selenylation reaction of aldehydes using a hypervalent iodine compound as an oxidative agent from commercially available phenyl diselenide under mild oxidative conditions is described. This transformation affords alpha-selenyl aldehydes in good yields and with excellent enantioselectivities. By using hypervalent iodine compounds, it opens up a suitable and alternative way for the preparation of biologically active building blocks such as beta-hydroxy alcohols, alpha-amino acids, and alpha-hydroxy esters. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.02.008

文献信息

• Highly enantioselective organocatalytic α-selenylation of aldehydes using hypervalent iodine compounds
  作者：Martin Kamlar、Jan Veselý

  DOI：10.1016/j.tetasy.2013.02.008

  日期：2013.3

  The highly enantioselective organocatalytic alpha-selenylation reaction of aldehydes using a hypervalent iodine compound as an oxidative agent from commercially available phenyl diselenide under mild oxidative conditions is described. This transformation affords alpha-selenyl aldehydes in good yields and with excellent enantioselectivities. By using hypervalent iodine compounds, it opens up a suitable and alternative way for the preparation of biologically active building blocks such as beta-hydroxy alcohols, alpha-amino acids, and alpha-hydroxy esters. (C) 2013 Elsevier Ltd. All rights reserved.