(S)-4-(1-(tert-butoxycarbonyl)piperidin-2-yl)butanoic acid | 1043392-05-7

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: (S)-4-(1-(tert-butoxycarbonyl)piperidin-2-yl)butanoic acid
• 英文别名: 4-[(2S)-1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-2-yl]butanoic acid
• CAS: 1043392-05-7
• 化学式: C₁₄H₂₅NO₄
• 分子量: 271.357
• InChiKey: DUJACCLQZZCXQA-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-4-(1-(tert-butoxycarbonyl)piperidin-2-yl)butanoic acid 在 三甲基氯硅烷 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 1.0h， 生成 4-[(2S)-piperidin-1-ium-2-yl]butanoate
  参考文献：
  名称：

  Enantioselective synthesis of (S)-1,6,7,8,9,9a-hexahydroquinolizin-4-one. Formal synthesis of the lycopodium alkaloids senepodine G and cermizine C

  摘要：

  The synthesis of the title compound, a key intermediate in the synthesis of some lycopodium and lupin alkaloids, is reported. From a stereochemical standpoint the key steps are the stereoselective cyclocondensation of ketodiester 1 with (R)-phenylglycinol and the stereocontrolled reduction, with retention of configuration, of the oxazolidine ring in the resulting oxazolopiperidone lactam 2. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.04.022
• 作为产物：
  描述：

  (S)-4-(1-(tert-butoxycarbonyl)piperidin-2-yl)butanal 在 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 作用下， 以 水 、 乙腈 、 叔丁醇 为溶剂， 反应 0.17h， 以85%的产率得到(S)-4-(1-(tert-butoxycarbonyl)piperidin-2-yl)butanoic acid
  参考文献：
  名称：

  Enantioselective synthesis of (S)-1,6,7,8,9,9a-hexahydroquinolizin-4-one. Formal synthesis of the lycopodium alkaloids senepodine G and cermizine C

  摘要：

  The synthesis of the title compound, a key intermediate in the synthesis of some lycopodium and lupin alkaloids, is reported. From a stereochemical standpoint the key steps are the stereoselective cyclocondensation of ketodiester 1 with (R)-phenylglycinol and the stereocontrolled reduction, with retention of configuration, of the oxazolidine ring in the resulting oxazolopiperidone lactam 2. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.04.022

文献信息

• Enantioselective synthesis of (S)-1,6,7,8,9,9a-hexahydroquinolizin-4-one. Formal synthesis of the lycopodium alkaloids senepodine G and cermizine C
  作者：Mercedes Amat、Rosa Griera、Robert Fabregat、Joan Bosch

  DOI：10.1016/j.tetasy.2008.04.022

  日期：2008.5

  The synthesis of the title compound, a key intermediate in the synthesis of some lycopodium and lupin alkaloids, is reported. From a stereochemical standpoint the key steps are the stereoselective cyclocondensation of ketodiester 1 with (R)-phenylglycinol and the stereocontrolled reduction, with retention of configuration, of the oxazolidine ring in the resulting oxazolopiperidone lactam 2. (C) 2008 Elsevier Ltd. All rights reserved.