methyl (2S,3aS)-2-methyl-3,3a,4,5,6,7-hexahydro-[1,2]oxazolo[2,3-a]pyridine-2-carboxylate | 116721-95-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: methyl (2S,3aS)-2-methyl-3,3a,4,5,6,7-hexahydro-[1,2]oxazolo[2,3-a]pyridine-2-carboxylate
• CAS: 116721-95-0；116722-01-1
• 化学式: C₁₀H₁₇NO₃
• 分子量: 199.25
• InChiKey: QVNCVDXQQBWGEQ-WPRPVWTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (2S,3aS)-2-methyl-3,3a,4,5,6,7-hexahydro-[1,2]oxazolo[2,3-a]pyridine-2-carboxylate 在 间氯过氧苯甲酸 作用下， 以 溶剂黄146 为溶剂， 生成 2-Hydroxy-2-methyl-3-(1-oxy-3,4,5,6-tetrahydro-pyridin-2-yl)-propionic acid methyl ester
  参考文献：
  名称：

  Peracid induced ring opening of isoxazolidines. A mechanistic study.

  摘要：

  Conformational analysis and mechanistic study of peracid induced ring opening of several isoxazolidines have been carried out. The orientation of the nitrogen lone pair dictates the regiochemistry of the ring opening which involves an intramolecular kinetic deprotonation of a nitroxonium ion intermediate.

  DOI：

  10.1016/s0040-4039(00)79856-x
• 作为产物：
  描述：

  diethyl 2-ethoxyhexahydro-2H-isoxazolo<2,3-a>pyridine-3,3-dicarboxylate 、 甲基丙烯酸甲酯 以 甲苯 为溶剂， 反应 8.0h， 生成 methyl (2S,3aS)-2-methyl-3,3a,4,5,6,7-hexahydro-[1,2]oxazolo[2,3-a]pyridine-2-carboxylate
  参考文献：
  名称：

  Ali, Sk. Asrof; Wazeer, Mohammed I. M., Journal of the Chemical Society. Perkin transactions II, 1990, # 6, p. 1035 - 1039

  摘要：

  DOI：

文献信息

• Reactivity, regiochemistry, and stereochemistry of a cyclic nitrone and its α-keto derivative in 1, 3-dipolar cycloaddition reactions
  作者：Sk.Asrof Ali、Mohammed I.M. Wazeer

  DOI：10.1016/s0040-4020(01)85105-x

  日期：1988.1

  Rate constants for the cycloadditions of 3,4,5,6-tetrahydropyridine 1-oxide (1) , and 3-oxo-3,4,5,6-tetrahydropyridine 1-oxide (2) to several mono- and disubstituted alkenes have been determined at 36°C by 1H NMR Spectroscopy. Small solvent effect on the rate constant indicate the concerted nature of the reaction. It is found that nitrone 2 reacts slower than 1 because of the presence of bond opposition

  3,4,5,6-四氢吡啶-1-氧化物（1）和3-氧代-3,4,5,6-四氢吡啶1-氧化物（2）与几种单或双取代烯烃的环加成反应的速率常数为在36°C下由1确定1 H NMR光谱。溶剂对速率常数的影响很小，表明反应是协调一致的。已经发现，由于在前一种硝酮的过渡态中存在键对立应变，因此硝酮2的反应比1慢。加成率受硝酮的偶极矩影响。这些加成反应的反应性通常遵循边界轨道近似的预测。两种硝酮均表现出非常相似的区域化学和立体化学性质。与几种缺电子的烯烃观察到显着的次级轨道相互作用。然而，发现马来酸酐主要通过exo攻击模式进行加成。
• Ali, Sk. Asrof; Wazeer, Mohammed I. M., Journal of the Chemical Society. Perkin transactions II, 1990, # 6, p. 1035 - 1039
  作者：Ali, Sk. Asrof、Wazeer, Mohammed I. M.

  DOI：——

  日期：——
• Peracid induced ring opening of isoxazolidines. A mechanistic study.
  作者：Sk.Asrof Ali、Mohammed I.M. Wazeer

  DOI：10.1016/s0040-4039(00)79856-x

  日期：1992.5

  Conformational analysis and mechanistic study of peracid induced ring opening of several isoxazolidines have been carried out. The orientation of the nitrogen lone pair dictates the regiochemistry of the ring opening which involves an intramolecular kinetic deprotonation of a nitroxonium ion intermediate.