methyl (2S,6S)-2-(2-hydroxyethyl)-6-propylpiperidine-1-carboxylate | 191665-90-4

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: methyl (2S,6S)-2-(2-hydroxyethyl)-6-propylpiperidine-1-carboxylate
• CAS: 191665-90-4
• 化学式: C₁₂H₂₃NO₃
• 分子量: 229.32
• InChiKey: LUXTWTAXTIQWIP-QWRGUYRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (2S,6S)-2-(2-hydroxyethyl)-6-propylpiperidine-1-carboxylate 在 吡啶 、 sodium iodide 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 17.5h， 生成 methyl (2S,6S)-(-)-2-(2-iodoethyl)-6-propylpiperidine-1-carboxylate
  参考文献：
  名称：

  Momose, Takefumi; Toshima, Minoru; Seki, Sumie, Journal of the Chemical Society. Perkin transactions I, 1997, # 9, p. 1315 - 1321

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl 3-oxo-9-azabicyclo[3.3.1]nonane-9-carboxylate 在 palladium on activated charcoal 六甲基磷酰三胺 、 正丁基锂 、 三氟甲磺酸 、 (S)-2,2-dimethyl-N-(2-(4-methylpiperazin-1-yl)-1-phenylethyl)propan-1-amine 、 氢气 、 diethylzinc 、 三乙基硼氢化锂 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 53.75h， 生成 methyl (2S,6S)-2-(2-hydroxyethyl)-6-propylpiperidine-1-carboxylate
  参考文献：
  名称：

  Hypervalent λn-iodane-mediated fragmentation of tertiary cyclopropanol systems II: Application to asymmetric syntheses of piperidine and indolizidine alkaloids

  摘要：

  The asymmetric synthesis of (-)-pinidine and its enantiomer was accomplished by starting from norgranatanone via the asymmetric enolization, stereoselective cyclopropanation, and oxidative ring cleavage of the resulting cyclopropanol system with a hypervalent lambda(n)-iodane as key steps. Formal asymmetric synthesis of (+)-indolizidine 223AB was also performed via the asymmetric enolization and oxidative ring cleavage of the resulting cyclopropanol system as key steps. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00073-3

文献信息

• Hypervalent λn-iodane-mediated fragmentation of tertiary cyclopropanol systems II: Application to asymmetric syntheses of piperidine and indolizidine alkaloids
  作者：Masayuki Kirihara、Takashi Nishio、Satoshi Yokoyama、Hiroko Kakuda、Takefumi Momose

  DOI：10.1016/s0040-4020(99)00073-3

  日期：1999.3

  The asymmetric synthesis of (-)-pinidine and its enantiomer was accomplished by starting from norgranatanone via the asymmetric enolization, stereoselective cyclopropanation, and oxidative ring cleavage of the resulting cyclopropanol system with a hypervalent lambda(n)-iodane as key steps. Formal asymmetric synthesis of (+)-indolizidine 223AB was also performed via the asymmetric enolization and oxidative ring cleavage of the resulting cyclopropanol system as key steps. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Momose, Takefumi; Toshima, Minoru; Seki, Sumie, Journal of the Chemical Society. Perkin transactions I, 1997, # 9, p. 1315 - 1321
  作者：Momose, Takefumi、Toshima, Minoru、Seki, Sumie、Koike, Yayoi、Toyooka, Naoki、Hirai, Yoshiro

  DOI：——

  日期：——