(4S)-4-benzyl-3-[(E)-5-(2-ethoxy-5-oxopyrrolidin-1-yl)pent-2-enoyl]oxazolidin-2-one | 951213-70-0

• 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: (4S)-4-benzyl-3-[(E)-5-(2-ethoxy-5-oxopyrrolidin-1-yl)pent-2-enoyl]oxazolidin-2-one
• 英文别名: (4S)-4-benzyl-3-[(E)-5-(2-ethoxy-5-oxopyrrolidin-1-yl)pent-2-enoyl]-1,3-oxazolidin-2-one
• CAS: 951213-70-0
• 化学式: C₂₁H₂₆N₂O₅
• 分子量: 386.448
• InChiKey: RNLYXRTVIMGTAL-CCGZFBSNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  76.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4S)-4-benzyl-3-[(E)-5-(2-ethoxy-5-oxopyrrolidin-1-yl)pent-2-enoyl]oxazolidin-2-one 在 四氯化钛 、 四丁基碘化铵 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 15.0h， 以45%的产率得到(7S,8R,8aS,4'S)-8-(4-benzyl-2-oxo-oxazolidin-3-ylcarbonyl)-7-iodohexahydroindolizin-3-one
  参考文献：
  名称：

  The intramolecular tandem Michael/Mannich-type reaction of α,β-unsaturated carbonyl compounds with acyliminium ions provides access to chiral indolizidines

  摘要：

  The intramolecular tandem Michael/Mannich-type (Michael addition/halo-Mannicli-type) reaction using TiCl4/n-BU(4)Nl system between the alpha,beta-unsaturated carbonyl compounds possessing an Evans oxazolidinone as a chiral auxiliary and N-acyliminium ion intermediates is described. The reaction was promoted in a mixed solvent of AcOEt-CH2O2 to afford indolizidine compounds with three stereogenic centers. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.06.009
• 作为产物：
  描述：

  N-(3-butenyl)succinimide 在 sodium tetrahydroborate 、 sodium hexamethyldisilazane 、 臭氧 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 正己烷 为溶剂， 反应 15.0h， 生成 (4S)-4-benzyl-3-[(E)-5-(2-ethoxy-5-oxopyrrolidin-1-yl)pent-2-enoyl]oxazolidin-2-one
  参考文献：
  名称：

  The intramolecular tandem Michael/Mannich-type reaction of α,β-unsaturated carbonyl compounds with acyliminium ions provides access to chiral indolizidines

  摘要：

  The intramolecular tandem Michael/Mannich-type (Michael addition/halo-Mannicli-type) reaction using TiCl4/n-BU(4)Nl system between the alpha,beta-unsaturated carbonyl compounds possessing an Evans oxazolidinone as a chiral auxiliary and N-acyliminium ion intermediates is described. The reaction was promoted in a mixed solvent of AcOEt-CH2O2 to afford indolizidine compounds with three stereogenic centers. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.06.009

文献信息

• The intramolecular tandem Michael/Mannich-type reaction of α,β-unsaturated carbonyl compounds with acyliminium ions provides access to chiral indolizidines
  作者：Yuji Koseki、Koji Fujino、Ai Takeshita、Hiroto Sato、Tatsuo Nagasaka

  DOI：10.1016/j.tetasy.2007.06.009

  日期：2007.7

  The intramolecular tandem Michael/Mannich-type (Michael addition/halo-Mannicli-type) reaction using TiCl4/n-BU(4)Nl system between the alpha,beta-unsaturated carbonyl compounds possessing an Evans oxazolidinone as a chiral auxiliary and N-acyliminium ion intermediates is described. The reaction was promoted in a mixed solvent of AcOEt-CH2O2 to afford indolizidine compounds with three stereogenic centers. (C) 2007 Elsevier Ltd. All rights reserved.