benzyl N-[(2S,4S)-4-methyl-1-phenylmethoxyhept-6-en-2-yl]carbamate | 1315606-56-4

• 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-[(2S,4S)-4-methyl-1-phenylmethoxyhept-6-en-2-yl]carbamate
• CAS: 1315606-56-4
• 化学式: C₂₃H₂₉NO₃
• 分子量: 367.488
• InChiKey: VMNRDNFRWZZERW-UGKGYDQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  27
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  benzyl N-[(2S,4S)-4-methyl-1-phenylmethoxyhept-6-en-2-yl]carbamate 在 Hoveyda-Grubbs catalyst second generation 、 三氟化硼乙醚 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 2.0h， 生成 benzyl (2S,4S,6S)-4-methyl-2-(2-oxoethyl)-6-(phenylmethoxymethyl)piperidine-1-carboxylate
  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：

  (S)-N-(2-(benzyloxy)ethylidene)-2-methylpropane-2-sulfinamide 在 盐酸 、 水 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 水 、 丙酮 、 甲苯 为溶剂， 反应 6.5h， 生成 benzyl N-[(2S,4S)-4-methyl-1-phenylmethoxyhept-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.