(5S)-6-oxo-7-((S)-1'-phenylethyl)-1,7-diazaspiro[4.4]nonane-1-carboxylic acid tert-butyl ester | 908264-65-3

• 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: (5S)-6-oxo-7-((S)-1'-phenylethyl)-1,7-diazaspiro[4.4]nonane-1-carboxylic acid tert-butyl ester
• 英文别名: 1,7-Diazaspiro[4.4]nonane-1-carboxylic acid,6-oxo-7-[(1S)-1-phenylethyl]-,1,1-dimethylethyl ester,(5S)-；tert-butyl (5S)-6-oxo-7-[(1S)-1-phenylethyl]-1,7-diazaspiro[4.4]nonane-1-carboxylate
• CAS: 908264-65-3
• 化学式: C₂₀H₂₈N₂O₃
• 分子量: 344.454
• InChiKey: KYRRSVXWTJYURJ-YWZLYKJASA-N

物化性质

• 沸点：
  497.9±38.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  49.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5S)-6-oxo-7-((S)-1'-phenylethyl)-1,7-diazaspiro[4.4]nonane-1-carboxylic acid tert-butyl ester 在 lithium aluminium tetrahydride 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (5S)-7-((S)-1'-phenylethyl)-1,7-diazaspiro[4.4]nonane
  参考文献：
  名称：

  Spirobicyclic diamines. Part 3: Synthesis and metal complexation of proline-derived [4.4]-spirodiamines

  摘要：

  The syntheses of racemic and homochiral [4.4]-spirolactams, starting from L-proline, in good yields are described. Reduction of the lactam carbonyl group of spirolactams, containing chiral substituents on the lactam nitrogen, with lithium aluminium hydride, gives a series of homochiral [4.4]- spirodiamines. The crystal structure of one of these spirodiamines on complexation with zinc chloride was obtained. Interestingly it showed a hydrogen-bonded dimeric structure, where the monomers are diastereoisomeric diamines. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.06.050
• 作为产物：
  描述：

  Boc-L-脯氨酸甲酯 在 sodium periodate 、 四氧化锇 、 水 、 sodium amide 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 生成 (5S)-6-oxo-7-((S)-1'-phenylethyl)-1,7-diazaspiro[4.4]nonane-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Spirobicyclic diamines. Part 3: Synthesis and metal complexation of proline-derived [4.4]-spirodiamines

  摘要：

  The syntheses of racemic and homochiral [4.4]-spirolactams, starting from L-proline, in good yields are described. Reduction of the lactam carbonyl group of spirolactams, containing chiral substituents on the lactam nitrogen, with lithium aluminium hydride, gives a series of homochiral [4.4]- spirodiamines. The crystal structure of one of these spirodiamines on complexation with zinc chloride was obtained. Interestingly it showed a hydrogen-bonded dimeric structure, where the monomers are diastereoisomeric diamines. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.06.050

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.