(4R)-3-((2S,3E)-2-methyl-4-phenylpent-3-enoyl)-4-phenyl-1,3-oxazolidin-2-one | 950489-64-2

• 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: (4R)-3-((2S,3E)-2-methyl-4-phenylpent-3-enoyl)-4-phenyl-1,3-oxazolidin-2-one
• 英文别名: (4R)-3-[(E,2S)-2-methyl-4-phenylpent-3-enoyl]-4-phenyl-1,3-oxazolidin-2-one
• CAS: 950489-64-2
• 化学式: C₂₁H₂₁NO₃
• 分子量: 335.403
• InChiKey: KVLUNOYITJBXOM-KYPGLKONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4R)-3-((2S,3E)-2-methyl-4-phenylpent-3-enoyl)-4-phenyl-1,3-oxazolidin-2-one 在 lithium hydroxide 、 双氧水 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (3R,4S,5R)-4-iodo-3,5-dimethyl-5-phenyldihydrofuran-2(3H)-one
  参考文献：
  名称：

  Preparation of enantiopure 3,5,5-trialkyl-γ-butyrolactones by diastereospecific 5-endo halo lactonizations

  摘要：

  A new preparation of 3,5,5-trialkyl-gamma-butyrolactones of defined absolute configuration is reported. This method involves the diastereoselective alkylation of 3,4-ethylenic acids after incorporation of a chiral Evans auxiliary, and then after separation of the two diastereomers and hydrolysis of the auxiliary, stereospecific halo lactonizations. This method was applied to the preparation of a natural product, present in a sponge. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.05.028
• 作为产物：
  描述：

  (R)-3-((E)-4-phenylpent-3-enoyl)-4-phenyloxazolidin-2-one 、 碘甲烷 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 正己烷 为溶剂， 反应 1.0h， 以36%的产率得到(R)-3-((R,E)-2-methyl-4-phenylpent-3-enoyl)-4-phenyloxazolidin-2-one
  参考文献：
  名称：

  Preparation of enantiopure 3,5,5-trialkyl-γ-butyrolactones by diastereospecific 5-endo halo lactonizations

  摘要：

  A new preparation of 3,5,5-trialkyl-gamma-butyrolactones of defined absolute configuration is reported. This method involves the diastereoselective alkylation of 3,4-ethylenic acids after incorporation of a chiral Evans auxiliary, and then after separation of the two diastereomers and hydrolysis of the auxiliary, stereospecific halo lactonizations. This method was applied to the preparation of a natural product, present in a sponge. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.05.028

文献信息

• Preparation of enantiopure 3,5,5-trialkyl-γ-butyrolactones by diastereospecific 5-endo halo lactonizations
  作者：Jean-Marc Garnier、Sylvie Robin、Régis Guillot、Gérard Rousseau

  DOI：10.1016/j.tetasy.2007.05.028

  日期：2007.7

  A new preparation of 3,5,5-trialkyl-gamma-butyrolactones of defined absolute configuration is reported. This method involves the diastereoselective alkylation of 3,4-ethylenic acids after incorporation of a chiral Evans auxiliary, and then after separation of the two diastereomers and hydrolysis of the auxiliary, stereospecific halo lactonizations. This method was applied to the preparation of a natural product, present in a sponge. (c) 2007 Elsevier Ltd. All rights reserved.