2-trimethylsilylethyl (3R,4R)-3-ethenyl-4-[(E)-3-(6-methoxyquinolin-4-yl)prop-2-enyl]piperidine-1-carboxylate | 865853-17-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-trimethylsilylethyl (3R,4R)-3-ethenyl-4-[(E)-3-(6-methoxyquinolin-4-yl)prop-2-enyl]piperidine-1-carboxylate
• CAS: 865853-17-4
• 化学式: C₂₆H₃₆N₂O₃Si
• 分子量: 452.669
• InChiKey: DMWHZTIHDGUTIZ-CPDQFQNSSA-N

物化性质

• 沸点：
  560.8±50.0 °C(predicted)
• 密度：
  1.089±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.25
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  51.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-trimethylsilylethyl (3R,4R)-3-ethenyl-4-[(E)-3-(6-methoxyquinolin-4-yl)prop-2-enyl]piperidine-1-carboxylate 在 AD-mix-α 作用下， 以68%的产率得到(3R,4S)-4-[(2S,3S)-2,3-Dihydroxy-3-(6-methoxy-quinolin-4-yl)-propyl]-3-vinyl-piperidine-1-carboxylic acid 2-trimethylsilanyl-ethyl ester
  参考文献：
  名称：

  Improved synthesis of quinine alkaloids with the Teoc protective group

  摘要：

  TeocCl (Teoc: C(=O)O(CH2)(2)TMS) generated in situ was conveniently used for trans-protection of the N-Bn piperidine intermediate to N-Teoc piperidine. Later, deprotection of the Teoc group and the subsequent quinuclidine ring formation was achieved with CsF in a domino fashion to afford the quinine alkaloids. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.06.171
• 作为产物：
  描述：

  2-(trimethylsilyl)ethyl (3R,4S)-4-(2-hydroxyethyl)-3-vinylpiperidine-1-carboxylate 在 sodium hydride 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 为溶剂， 生成 2-trimethylsilylethyl (3R,4R)-3-ethenyl-4-[(E)-3-(6-methoxyquinolin-4-yl)prop-2-enyl]piperidine-1-carboxylate
  参考文献：
  名称：

  Improved synthesis of quinine alkaloids with the Teoc protective group

  摘要：

  TeocCl (Teoc: C(=O)O(CH2)(2)TMS) generated in situ was conveniently used for trans-protection of the N-Bn piperidine intermediate to N-Teoc piperidine. Later, deprotection of the Teoc group and the subsequent quinuclidine ring formation was achieved with CsF in a domino fashion to afford the quinine alkaloids. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.06.171

文献信息

• Improved synthesis of quinine alkaloids with the Teoc protective group
  作者：Junji Igarashi、Yuichi Kobayashi

  DOI：10.1016/j.tetlet.2005.06.171

  日期：2005.9

  TeocCl (Teoc: C(=O)O(CH2)(2)TMS) generated in situ was conveniently used for trans-protection of the N-Bn piperidine intermediate to N-Teoc piperidine. Later, deprotection of the Teoc group and the subsequent quinuclidine ring formation was achieved with CsF in a domino fashion to afford the quinine alkaloids. (c) 2005 Elsevier Ltd. All rights reserved.