tert-butyl (6R)-6-[[(2S)-4-methyl-6-oxo-2,5-dihydropyran-2-yl]methyl]-3,6-dihydro-2H-pyridine-1-carboxylate | 916318-77-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: tert-butyl (6R)-6-[[(2S)-4-methyl-6-oxo-2,5-dihydropyran-2-yl]methyl]-3,6-dihydro-2H-pyridine-1-carboxylate
• CAS: 916318-77-9
• 化学式: C₁₇H₂₅NO₄
• 分子量: 307.39
• InChiKey: QDOHULSMNRPHQR-UONOGXRCSA-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：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (6R)-6-[[(2S)-4-methyl-6-oxo-2,5-dihydropyran-2-yl]methyl]-3,6-dihydro-2H-pyridine-1-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Catalytic enantioselective total synthesis of (+)-dumetorine by ring-rearrangement metathesis

  摘要：

  A concise, enantioselective synthesis of (+)-dumetorine is described, giving the natural product in six steps and a 27% overall yield from a readily available precursor. Among the key steps used, the synthesis entails a high-yielding ring-rearrangement metathesis (RRM), using the commercially available first generation Grubbs catalyst 2 in combination with Ti(Oi-Pr)(4) as a co-catalyst. This constitutes the first enantioselective total synthesis of the alkaloid from a known chiral intermediate, and hence a confirmation of its absolute stereochemistry. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.08.114
• 作为产物：
  描述：

  [(1S,4R)-4-[but-3-enyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]cyclopent-2-en-1-yl] 3-methylbut-3-enoate 在 titanium(IV) isopropylate 、 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 反应 36.0h， 以80%的产率得到tert-butyl (6R)-6-[[(2S)-4-methyl-6-oxo-2,5-dihydropyran-2-yl]methyl]-3,6-dihydro-2H-pyridine-1-carboxylate
  参考文献：
  名称：

  Catalytic enantioselective total synthesis of (+)-dumetorine by ring-rearrangement metathesis

  摘要：

  A concise, enantioselective synthesis of (+)-dumetorine is described, giving the natural product in six steps and a 27% overall yield from a readily available precursor. Among the key steps used, the synthesis entails a high-yielding ring-rearrangement metathesis (RRM), using the commercially available first generation Grubbs catalyst 2 in combination with Ti(Oi-Pr)(4) as a co-catalyst. This constitutes the first enantioselective total synthesis of the alkaloid from a known chiral intermediate, and hence a confirmation of its absolute stereochemistry. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.08.114

文献信息

• Catalytic enantioselective total synthesis of (+)-dumetorine by ring-rearrangement metathesis
  作者：Anke Rückert、Prashant H. Deshmukh、Siegfried Blechert

  DOI：10.1016/j.tetlet.2006.08.114

  日期：2006.11

  A concise, enantioselective synthesis of (+)-dumetorine is described, giving the natural product in six steps and a 27% overall yield from a readily available precursor. Among the key steps used, the synthesis entails a high-yielding ring-rearrangement metathesis (RRM), using the commercially available first generation Grubbs catalyst 2 in combination with Ti(Oi-Pr)(4) as a co-catalyst. This constitutes the first enantioselective total synthesis of the alkaloid from a known chiral intermediate, and hence a confirmation of its absolute stereochemistry. (c) 2006 Elsevier Ltd. All rights reserved.