methyl (3S,4R)-4-{[(1R,2R)-2-hydroxy-1-methylpropyl]oxy}-4-phenyl-3-(phenylseleno)butanoate | 586953-81-3

• 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: methyl (3S,4R)-4-{[(1R,2R)-2-hydroxy-1-methylpropyl]oxy}-4-phenyl-3-(phenylseleno)butanoate
• CAS: 586953-81-3
• 化学式: C₂₁H₂₆O₄Se
• 分子量: 421.395
• InChiKey: ZVUZWOQWHBZOJG-DCTVWTRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.89
• 重原子数：
  26.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl (3S,4R)-4-{[(1R,2R)-2-hydroxy-1-methylpropyl]oxy}-4-phenyl-3-(phenylseleno)butanoate 在 双氧水 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 methyl [(2R,3R,5R,6R)-5,6-dimethyl-3-phenyl-1,4-dioxan-2-yl]acetate
  参考文献：
  名称：

  Synthesis of enantiomerically pure 1,4-dioxanes from alkenes promoted by organoselenium reagents

  摘要：

  An alkene can be converted into two enantiomerically pure diastereomeric selenoethers through a regio- and stereospecific anti addition reaction mediated by N-(phenylseleno)phthalimide in the presence of an enantiomerically pure 1,2-diol. This alkoxyselenylation reaction can be employed as the key step to allow the synthesis of several isomeric tetrasubstituted 1,4-dioxanes in enantiomerically pure form. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00124-1
• 作为产物：
  描述：

  N-(苯硒基)邻苯二甲酰亚胺 、 (2R,3R)-(-)-2,3-丁二醇 、 (E)-methyl 4-phenylbut-3-enoate 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以31%的产率得到methyl (3S,4R)-4-{[(1R,2R)-2-hydroxy-1-methylpropyl]oxy}-4-phenyl-3-(phenylseleno)butanoate
  参考文献：
  名称：

  Synthesis of enantiomerically pure 1,4-dioxanes from alkenes promoted by organoselenium reagents

  摘要：

  An alkene can be converted into two enantiomerically pure diastereomeric selenoethers through a regio- and stereospecific anti addition reaction mediated by N-(phenylseleno)phthalimide in the presence of an enantiomerically pure 1,2-diol. This alkoxyselenylation reaction can be employed as the key step to allow the synthesis of several isomeric tetrasubstituted 1,4-dioxanes in enantiomerically pure form. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00124-1

文献信息

• Synthesis of enantiomerically pure 1,4-dioxanes from alkenes promoted by organoselenium reagents
  作者：Marcello Tiecco、Lorenzo Testaferri、Francesca Marini、Silvia Sternativo、Claudio Santi、Luana Bagnoli、Andrea Temperini

  DOI：10.1016/s0957-4166(03)00124-1

  日期：2003.5

  An alkene can be converted into two enantiomerically pure diastereomeric selenoethers through a regio- and stereospecific anti addition reaction mediated by N-(phenylseleno)phthalimide in the presence of an enantiomerically pure 1,2-diol. This alkoxyselenylation reaction can be employed as the key step to allow the synthesis of several isomeric tetrasubstituted 1,4-dioxanes in enantiomerically pure form. (C) 2003 Elsevier Science Ltd. All rights reserved.