(S)-7-((R)-1-Methoxycarbonyl-ethyl)-6-oxo-1,7-diaza-spiro[4.4]nonane-1-carboxylic acid tert-butyl ester

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-7-((R)-1-Methoxycarbonyl-ethyl)-6-oxo-1,7-diaza-spiro[4.4]nonane-1-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (5S)-7-[(2R)-1-methoxy-1-oxopropan-2-yl]-6-oxo-1,7-diazaspiro[4.4]nonane-1-carboxylate
• 化学式: C₁₆H₂₆N₂O₅
• 分子量: 326.393
• InChiKey: LZOKLAQWQMJAOD-BZNIZROVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  76.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-tert-butyl 2-methyl 2-(2-oxoethyl)pyrrolidine-1,2-dicarboxylate 在 sodium tetrahydroborate 、 magnesium sulfate 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 72.0h， 生成 (S)-7-((R)-1-Methoxycarbonyl-ethyl)-6-oxo-1,7-diaza-spiro[4.4]nonane-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Spirobicyclic diamines. Part 2: Synthesis of homochiral diastereoisomeric proline derived [4.4]-spirolactams

  摘要：

  L-Proline derived diastereoisomeric [4.4]-spirolactams have been prepared by a reductive-amination reaction of (R)- or (S)-alanine methyl ester, followed by thermal cyclisation of the resulting amine onto the proline ester group in refluxing toluene. Under similar conditions (R)- or (S)-phenylalanine methyl ester gave no cyclisation products, while R- or S-alpha-methylbenzylamine required treatment with NaNH2 in refluxing toluene to induce cyclisation giving diastereoisomeric [4.4]-spirolactams. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.05.154

文献信息

• Spirobicyclic diamines. Part 2: Synthesis of homochiral diastereoisomeric proline derived [4.4]-spirolactams
  作者：Fintan Kelleher、Sinead Kelly

  DOI：10.1016/j.tetlet.2006.05.154

  日期：2006.7

  L-Proline derived diastereoisomeric [4.4]-spirolactams have been prepared by a reductive-amination reaction of (R)- or (S)-alanine methyl ester, followed by thermal cyclisation of the resulting amine onto the proline ester group in refluxing toluene. Under similar conditions (R)- or (S)-phenylalanine methyl ester gave no cyclisation products, while R- or S-alpha-methylbenzylamine required treatment with NaNH2 in refluxing toluene to induce cyclisation giving diastereoisomeric [4.4]-spirolactams. (c) 2006 Elsevier Ltd. All rights reserved.