(S)-4-methyl-6-((R)-1-methyl-1,2,5,6-tetrahydropyridin-2-ylmethyl)-5,6-dihydropyran-2-one | 916318-78-0

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (S)-4-methyl-6-((R)-1-methyl-1,2,5,6-tetrahydropyridin-2-ylmethyl)-5,6-dihydropyran-2-one
• CAS: 916318-78-0
• 化学式: C₁₃H₁₉NO₂
• 分子量: 221.299
• InChiKey: OERKHEVYVPTAKZ-NWDGAFQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (S)-4-methyl-6-((R)-1-methyl-1,2,5,6-tetrahydropyridin-2-ylmethyl)-5,6-dihydropyran-2-one 在 Wilkinson's catalyst 氢气 作用下， 以 乙醇 、 苯 为溶剂， 25.0 ℃ 、101.32 kPa 条件下， 反应 4.0h， 以100%的产率得到(+)-4-methyl-6-(1-methylpiperidine-2-ylmethyl)-5,6-dihydropyran-2-one
  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 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 40.0h， 生成 (S)-4-methyl-6-((R)-1-methyl-1,2,5,6-tetrahydropyridin-2-ylmethyl)-5,6-dihydropyran-2-one
  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