ethyl N-[(benzyloxy)carbonyl]-3-(1-hydroxycyclopropyl)alaninate | 862205-18-3

• 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: ethyl N-[(benzyloxy)carbonyl]-3-(1-hydroxycyclopropyl)alaninate
• 英文别名: Ethyl 3-(1-hydroxycyclopropyl)-2-(phenylmethoxycarbonylamino)propanoate
• CAS: 862205-18-3
• 化学式: C₁₆H₂₁NO₅
• 分子量: 307.346
• InChiKey: MNWLGIIJCJYJFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl N-[(benzyloxy)carbonyl]-3-(1-hydroxycyclopropyl)alaninate 在 palladium diacetate 吡啶 、 氧气 作用下， 以 甲苯 为溶剂， 80.0 ℃ 、506.62 kPa 条件下， 反应 3.0h， 以95%的产率得到ethyl 2-{[(benzyloxy)carbonyl]amino}-4-oxohex-5-enoate
  参考文献：
  名称：

  Two-Step Metal-Mediated Transformation of Isoxazolidine-5-spirocyclopropanes into Pyridone Derivatives

  摘要：

  The two-step metal-catalyzed overall transformation of isoxazolidine-5-spirocyclopropanes into the corresponding dihydro- and tetrahydropyridones is described. The first step is the chemoselective reduction of the N-O bond of the isoxazolidine ring preserving the fragile cyclopropanol moiety while the second transformation is the Pd(II) or Pd(O) conversion of the beta-aminocyclopropanol derivatives into the final compounds. The scope and limitations of this strategy are described.

  DOI：

  10.1021/jo050640q
• 作为产物：
  描述：

  ethyl 5-(phenylmethyl)-4-oxa-5-azaspiro[2.4]heptane-6-carboxylate 在 palladium dihydroxide 氢气 、 碳酸氢钠 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 反应 3.0h， 生成 ethyl N-[(benzyloxy)carbonyl]-3-(1-hydroxycyclopropyl)alaninate
  参考文献：
  名称：

  Two-Step Metal-Mediated Transformation of Isoxazolidine-5-spirocyclopropanes into Pyridone Derivatives

  摘要：

  The two-step metal-catalyzed overall transformation of isoxazolidine-5-spirocyclopropanes into the corresponding dihydro- and tetrahydropyridones is described. The first step is the chemoselective reduction of the N-O bond of the isoxazolidine ring preserving the fragile cyclopropanol moiety while the second transformation is the Pd(II) or Pd(O) conversion of the beta-aminocyclopropanol derivatives into the final compounds. The scope and limitations of this strategy are described.

  DOI：

  10.1021/jo050640q

文献信息

• Two-Step Metal-Mediated Transformation of Isoxazolidine-5-spirocyclopropanes into Pyridone Derivatives
  作者：Julia Revuelta、Stefano Cicchi、Alberto Brandi

  DOI：10.1021/jo050640q

  日期：2005.7.1

  The two-step metal-catalyzed overall transformation of isoxazolidine-5-spirocyclopropanes into the corresponding dihydro- and tetrahydropyridones is described. The first step is the chemoselective reduction of the N-O bond of the isoxazolidine ring preserving the fragile cyclopropanol moiety while the second transformation is the Pd(II) or Pd(O) conversion of the beta-aminocyclopropanol derivatives into the final compounds. The scope and limitations of this strategy are described.