benzyl N-[(E,2S,4S)-4-methyl-8-oxo-1-phenylmethoxyoct-6-en-2-yl]carbamate | 1315606-51-9

• 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: benzyl N-[(E,2S,4S)-4-methyl-8-oxo-1-phenylmethoxyoct-6-en-2-yl]carbamate
• CAS: 1315606-51-9
• 化学式: C₂₄H₂₉NO₄
• 分子量: 395.499
• InChiKey: QUCWYXRHUHQOEG-WWQISKJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  29
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  benzyl N-[(E,2S,4S)-4-methyl-8-oxo-1-phenylmethoxyoct-6-en-2-yl]carbamate 在 palladium 10% on activated carbon 、 三氟化硼乙醚 、 氢气 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 乙酸乙酯 、 乙腈 、 苯 为溶剂， 20.0~144.0 ℃ 、101.33 kPa 条件下， 反应 65.0h， 生成 C₁₁H₁₉NO₂
  参考文献：
  名称：

  Stereoselective Synthesis of the Eastern Quinolizidine Portion of Himeradine A

  摘要：

  The synthesis of the C-15-C-17/N-1'-C-11', quinolizidine portion of himeradine A is disclosed. An intramolecular, heteroatom Michael addition was employed to establish the C-6' stereogenic center with high dlastereoselectivity. The quinolizidine ring was constructed using microwave-induced cyclization at the N-1'-C-2' position. The C-17 stereogenic center was introduced through a diastereoselective Overman rearrangement.

  DOI：

  10.1021/ol201704g
• 作为产物：
  描述：

  C₁₅H₂₃NO*ClH 在 Hoveyda-Grubbs catalyst second generation 、 potassium carbonate 作用下， 以 二氯甲烷 、 水 、 丙酮 、 甲苯 为溶剂， 反应 2.0h， 生成 benzyl N-[(E,2S,4S)-4-methyl-8-oxo-1-phenylmethoxyoct-6-en-2-yl]carbamate
  参考文献：
  名称：

  Stereoselective Synthesis of the Eastern Quinolizidine Portion of Himeradine A

  摘要：

  The synthesis of the C-15-C-17/N-1'-C-11', quinolizidine portion of himeradine A is disclosed. An intramolecular, heteroatom Michael addition was employed to establish the C-6' stereogenic center with high dlastereoselectivity. The quinolizidine ring was constructed using microwave-induced cyclization at the N-1'-C-2' position. The C-17 stereogenic center was introduced through a diastereoselective Overman rearrangement.

  DOI：

  10.1021/ol201704g

文献信息

• Stereoselective Synthesis of the Eastern Quinolizidine Portion of Himeradine A
  作者：Nathan D. Collett、Rich G. Carter

  DOI：10.1021/ol201704g

  日期：2011.8.5

  The synthesis of the C-15-C-17/N-1'-C-11', quinolizidine portion of himeradine A is disclosed. An intramolecular, heteroatom Michael addition was employed to establish the C-6' stereogenic center with high dlastereoselectivity. The quinolizidine ring was constructed using microwave-induced cyclization at the N-1'-C-2' position. The C-17 stereogenic center was introduced through a diastereoselective Overman rearrangement.