(E)-3,3'-(1,4-dioxo-2-butene-1,4-diyl)bis[2,2-dimethyl-(S)-4-(1,1-dimethylethyl)]-1,3-oxazolidine | 291531-24-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (E)-3,3'-(1,4-dioxo-2-butene-1,4-diyl)bis[2,2-dimethyl-(S)-4-(1,1-dimethylethyl)]-1,3-oxazolidine
• 英文别名: (E)-1,4-bis[(4S)-4-tert-butyl-2,2-dimethyl-1,3-oxazolidin-3-yl]but-2-ene-1,4-dione
• CAS: 291531-24-3
• 化学式: C₂₂H₃₈N₂O₄
• 分子量: 394.555
• InChiKey: FWKDDDQPQAOYAN-NFGWICIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  四丁基锡 、 (E)-3,3'-(1,4-dioxo-2-butene-1,4-diyl)bis[2,2-dimethyl-(S)-4-(1,1-dimethylethyl)]-1,3-oxazolidine 在 联苯 、 DCN 作用下， 以 乙腈 为溶剂， 以79%的产率得到3,3'-[(S)-2-butyl-1,4-dioxo-1,4-butanediyl]bis[2,2-dimethyl-(S)-4-(1,1-dimethylethyl)]oxazolidine
  参考文献：
  名称：

  Diastereoselective photosensitised radical addition to fumaric acid derivatives bearing oxazolidine chiral auxiliaries

  摘要：

  Various fumaric acid diamides were alkylated by reaction with photogenerated radicals. The radicals were produced either by benzophenone triplet hydrogen abstraction (from 1,3-dioxolane, 2-methyl-1,3-dioxolane and adamantane) or via photoinduced electron transfer sensitised by DCN/biphenyl from stannanes (t-BuSnPh3 and Bu4Sn). When chiral substrates were employed the reaction occurred with a good degree of stereoselectivity even when acyclic alkyl radicals were involved. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00138-5
• 作为产物：
  描述：

  反丁烯二酰氯 、 (4S)-4-tert-butyl-2,2-dimethyl-1,3-oxazolidine 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 以15%的产率得到(E)-3,3'-(1,4-dioxo-2-butene-1,4-diyl)bis[2,2-dimethyl-(S)-4-(1,1-dimethylethyl)]-1,3-oxazolidine
  参考文献：
  名称：

  Diastereoselective photosensitised radical addition to fumaric acid derivatives bearing oxazolidine chiral auxiliaries

  摘要：

  Various fumaric acid diamides were alkylated by reaction with photogenerated radicals. The radicals were produced either by benzophenone triplet hydrogen abstraction (from 1,3-dioxolane, 2-methyl-1,3-dioxolane and adamantane) or via photoinduced electron transfer sensitised by DCN/biphenyl from stannanes (t-BuSnPh3 and Bu4Sn). When chiral substrates were employed the reaction occurred with a good degree of stereoselectivity even when acyclic alkyl radicals were involved. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00138-5

文献信息

• Diastereoselective photosensitised radical addition to fumaric acid derivatives bearing oxazolidine chiral auxiliaries
  作者：Gigliola Campari、Maurizio Fagnoni、Mariella Mella、Angelo Albini

  DOI：10.1016/s0957-4166(00)00138-5

  日期：2000.5

  Various fumaric acid diamides were alkylated by reaction with photogenerated radicals. The radicals were produced either by benzophenone triplet hydrogen abstraction (from 1,3-dioxolane, 2-methyl-1,3-dioxolane and adamantane) or via photoinduced electron transfer sensitised by DCN/biphenyl from stannanes (t-BuSnPh3 and Bu4Sn). When chiral substrates were employed the reaction occurred with a good degree of stereoselectivity even when acyclic alkyl radicals were involved. (C) 2000 Elsevier Science Ltd. All rights reserved.