(S)-tert-butyl-6-(benzyloxymethyl)-5,6-dihydropyridine-1(2H)-carboxylate | 1201635-96-2

• 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: (S)-tert-butyl-6-(benzyloxymethyl)-5,6-dihydropyridine-1(2H)-carboxylate
• 英文别名: tert-butyl (2S)-2-(phenylmethoxymethyl)-3,6-dihydro-2H-pyridine-1-carboxylate
• CAS: 1201635-96-2
• 化学式: C₁₈H₂₅NO₃
• 分子量: 303.401
• InChiKey: PUPCWZZYQUMMPE-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-tert-butyl-6-(benzyloxymethyl)-5,6-dihydropyridine-1(2H)-carboxylate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 25.0 ℃ 、137.9 kPa 条件下， 反应 8.0h， 以88%的产率得到(S)-N-Boc-2-哌啶甲醇
  参考文献：
  名称：

  A concise enantioselective synthesis of (+)-lentiginosine

  摘要：

  A high yielding enantioselective synthesis of the indolizidine alkaloid, (+)-lentiginosine, has been described based on asymmetric oza-Cope rearrangement and the L-proline catalyzed alpha-aminooxylation of aldehydes. The strategy also makes use of ring-closing metathesis for the construction of piperidine core. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.08.027
• 作为产物：
  描述：

  tert-butyl allyl-(S)-1-(benzyloxy)pent-4-en-2-ylcarbamate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 反应 22.0h， 以78%的产率得到(S)-tert-butyl-6-(benzyloxymethyl)-5,6-dihydropyridine-1(2H)-carboxylate
  参考文献：
  名称：

  A concise enantioselective synthesis of (+)-lentiginosine

  摘要：

  A high yielding enantioselective synthesis of the indolizidine alkaloid, (+)-lentiginosine, has been described based on asymmetric oza-Cope rearrangement and the L-proline catalyzed alpha-aminooxylation of aldehydes. The strategy also makes use of ring-closing metathesis for the construction of piperidine core. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.08.027

文献信息

• A concise enantioselective synthesis of (+)-lentiginosine
  作者：Tanveer Mahamadali Shaikh、Arumugam Sudalai

  DOI：10.1016/j.tetasy.2009.08.027

  日期：2009.10

  A high yielding enantioselective synthesis of the indolizidine alkaloid, (+)-lentiginosine, has been described based on asymmetric oza-Cope rearrangement and the L-proline catalyzed alpha-aminooxylation of aldehydes. The strategy also makes use of ring-closing metathesis for the construction of piperidine core. (C) 2009 Elsevier Ltd. All rights reserved.