(2S,5S)-1-benzoyl-2-tert-butyl-3-methyl-5-prop-2-enylimidazolidin-4-one | 157401-59-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,5S)-1-benzoyl-2-tert-butyl-3-methyl-5-prop-2-enylimidazolidin-4-one
• CAS: 157401-59-7
• 化学式: C₁₈H₂₄N₂O₂
• 分子量: 300.401
• InChiKey: CHQREDYYBJIYRJ-YOEHRIQHSA-N

物化性质

• 沸点：
  451.8±38.0 °C(Predicted)
• 密度：
  1.073±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S,5S)-1-benzoyl-2-tert-butyl-3-methyl-5-prop-2-enylimidazolidin-4-one 在 盐酸 、 水 、 碘 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 L-羟基脯氨酸
  参考文献：
  名称：

  A short stereoselective synthesis of cis- and trans-4-hydroxyl-L-proline

  摘要：

  A concise three-step synthesis of cis- and trans-4-hydroxy-L-proline on a preparative scale has been carried out using readily available starting materials.

  DOI：

  10.1039/c39940001291
• 作为产物：
  描述：

  (2S)-(+)-1-苯甲酰基-2-叔丁基-3-甲基-4-咪唑啉酮 、 3-溴丙烯 在 正丁基锂 、 lithium diisopropyl amide 作用下， 反应 3.0h， 以90%的产率得到(2S,5S)-1-benzoyl-2-tert-butyl-3-methyl-5-prop-2-enylimidazolidin-4-one
  参考文献：
  名称：

  A short stereoselective synthesis of cis- and trans-4-hydroxyl-L-proline

  摘要：

  A concise three-step synthesis of cis- and trans-4-hydroxy-L-proline on a preparative scale has been carried out using readily available starting materials.

  DOI：

  10.1039/c39940001291

文献信息

• Stereospecific Synthesis of (2<i>S</i>,4<i>S</i>,6<i>S</i>)-2-Amino-4,6-Dihydroxypimelic Acid
  作者：Michaela Mehlführer、Klaus Thirring、Heinz Berner

  DOI：10.1021/jo970307p

  日期：1997.6.13

  The Lewis acid catalyzed stereoselective carbonyl-ene-reaction between (2S,5S)-1-benzoyl-2-tert-butyl-3-methyl-5-(2-propenyl) imidazolidin-4-one (2) and anhydrous butyl glyoxylate was investigated with the aim to obtain highly functionalized amino acids. This reaction is assumed to proceed in a nonsynchronous fashion, giving rise to competing reactions within the time interval between the C-C bond formation and the proton migration step. Thus, a hypothesized dipolar intermediate could undergo two reaction pathways: besides conventional ene product 3, two further products 4 and 5 are obtained via nucleophilic attack involving two different neighboring carbamoyl groups. Acidic hydrolysis of both products afforded title compound 1. The absolute configuration of the two newly formed chiral centers was assigned by NMR measurements of lactone 4 and its rigid derivative 7. By varying the temperature (-20 degrees to 25 degrees C) and the type of Lewis acid (SnCl4, FeCl3) the reaction can be directed to give either of the possible reaction products. A plausible reaction mechanism is proposed.
• A short stereoselective synthesis of cis- and trans-4-hydroxyl-<scp>L</scp>-proline
  作者：Michaela Mehlführer、Heinz Berner、Klaus Thirring

  DOI：10.1039/c39940001291

  日期：——

  A concise three-step synthesis of cis- and trans-4-hydroxy-L-proline on a preparative scale has been carried out using readily available starting materials.