N-(benzyloxycarbonyl)-(6S)-6-n-propylpiperidin-4-one | 142764-70-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(benzyloxycarbonyl)-(6S)-6-n-propylpiperidin-4-one
• 英文别名: (2S)-benzyl 2-propyl-4-oxopiperidine-1-carboxylate；(S)-Benzyl 4-oxo-2-propylpiperidine-1-carboxylate；benzyl (2S)-4-oxo-2-propylpiperidine-1-carboxylate
• CAS: 142764-70-3
• 化学式: C₁₆H₂₁NO₃
• 分子量: 275.348
• InChiKey: NXTIKFGDQYVIFK-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  N-(benzyloxycarbonyl)-(6S)-6-n-propylpiperidin-4-one 在 4 A molecular sieve 、 三氟化硼乙醚 、 氢气 、 镍 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 生成 2-丙六氢吡啶盐酸盐
  参考文献：
  名称：

  Asymmetric tandem Mannich-Michael reactions of amino acid ester imines with Danishefsky's diene

  摘要：

  Imines 1 derived from aromatic, aliphatic, and functionalized aldehydes and various amino acid esters react with Danishefsky's diene under Lewis acid catalysis via a tandem Mannich-Michael mechanism to give cyclic 6-substituted 2,3-didehydro-4-piperidinones in good to high yields and with diastereomeric ratios reaching from 92:8 up to 97:3. The chiral auxiliary is removed by conversion of the alpha-C atom of the amino acid into an acetalic center, employing a Curtius reaction as the key step. For the elucidation of the absolute configuration, the alkaloids (S)-coniine and (R)-delta-coniceine are synthesized from the enaminones 5i and 5r.

  DOI：

  10.1021/jo00042a027
• 作为产物：
  描述：

  (2S)-1-(benzyloxycarbonyl)-2,3-dihydro-2-propylpyridine-4(1H)-one 在 L-Selectride 作用下， 以 四氢呋喃 为溶剂， 以81%的产率得到N-(benzyloxycarbonyl)-(6S)-6-n-propylpiperidin-4-one
  参考文献：
  名称：

  Waldmann, Herbert; Braun, Matthias; Draeger, Martin, Angewandte Chemie, 1990, vol. 102, # 12, p. 1445 - 1447

  摘要：

  DOI：

文献信息

• Highly Enantioselective Catalytic Addition of Grignard Reagents to N‐Heterocyclic Acceptors
  作者：Yafei Guo、Syuzanna R. Harutyunyan

  DOI：10.1002/anie.201906237

  日期：2019.9.9

  greatly sought after because of their significance in medicinal chemistry. Described here is the first general catalytic methodology to access a wide variety of chiral 2‐ and 4‐substituted tetrahydro‐quinolones, dihydro‐4‐pyridones, and piperidones with excellent yields and enantioselectivities, utilizing a single catalyst system.

  由于手性N-杂环分子支架在药物化学中的重要性，因此备受追捧。这里描述的是第一种通用催化方法，它利用单一催化剂系统，以优异的收率和对映选择性获得了各种手性2和4取代的四氢喹诺酮，二氢4吡啶酮和哌啶酮。
• Waldmann, Herbert; Braun, Matthias; Draeger, Martin, Angewandte Chemie, 1990, vol. 102, # 12, p. 1445 - 1447
  作者：Waldmann, Herbert、Braun, Matthias、Draeger, Martin

  DOI：——

  日期：——
• Asymmetric tandem Mannich-Michael reactions of amino acid ester imines with Danishefsky's diene
  作者：H. Waldmann、M. Braun

  DOI：10.1021/jo00042a027

  日期：1992.7

  Imines 1 derived from aromatic, aliphatic, and functionalized aldehydes and various amino acid esters react with Danishefsky's diene under Lewis acid catalysis via a tandem Mannich-Michael mechanism to give cyclic 6-substituted 2,3-didehydro-4-piperidinones in good to high yields and with diastereomeric ratios reaching from 92:8 up to 97:3. The chiral auxiliary is removed by conversion of the alpha-C atom of the amino acid into an acetalic center, employing a Curtius reaction as the key step. For the elucidation of the absolute configuration, the alkaloids (S)-coniine and (R)-delta-coniceine are synthesized from the enaminones 5i and 5r.