(S)-1-(2,2,2-Trifluoro-acetyl)-piperidine-2-carboxylic acid (S)-3,4,4-trimethyl-2-oxo-tetrahydro-furan-3-yl ester | 596129-26-9

• 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)-1-(2,2,2-Trifluoro-acetyl)-piperidine-2-carboxylic acid (S)-3,4,4-trimethyl-2-oxo-tetrahydro-furan-3-yl ester
• 英文别名: [(3S)-3,4,4-trimethyl-2-oxooxolan-3-yl] (2S)-1-(2,2,2-trifluoroacetyl)piperidine-2-carboxylate
• CAS: 596129-26-9
• 化学式: C₁₅H₂₀F₃NO₅
• 分子量: 351.323
• InChiKey: SUFYZJRIIOYLNM-LKFCYVNXSA-N

物化性质

• 熔点：
  108-110 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  468.7±45.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  二碳酸二叔丁酯 、 (S)-1-(2,2,2-Trifluoro-acetyl)-piperidine-2-carboxylic acid (S)-3,4,4-trimethyl-2-oxo-tetrahydro-furan-3-yl ester 在 sodium hydroxide 作用下， 以 四氢呋喃 、 水 、 1,4-二氧六环 为溶剂， 反应 24.0h， 生成 N-Boc-D-哌啶-2-羧酸 、 N-Boc-L-哌啶-2-羧酸
  参考文献：
  名称：

  Diastereoselective esterification of (±)-N-trifluoroacetyl pipecolic acid using (S)-α-methyl pantolactone: synthesis of (S)-N-Boc pipecolic acid and (S)-N-Boc-2-piperidinemethanol

  摘要：

  Racemic N-trifluoroacetyl pipecolic acid has been converted into (S)-N-Boc-pipecolic acid or (S)-N-Boc-2-piperidinemethanol by DCC/DMAP-induced diastereoselective esterification with (S)-alpha-methyl pantolactone, followed by a saponification or a reduction reaction and N-Boc protection. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00304-5
• 作为产物：
  描述：

  六氢吡啶-alpha-羧酸 在 4-二甲氨基吡啶 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 15.0h， 生成 (S)-1-(2,2,2-Trifluoro-acetyl)-piperidine-2-carboxylic acid (S)-3,4,4-trimethyl-2-oxo-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  Diastereoselective esterification of (±)-N-trifluoroacetyl pipecolic acid using (S)-α-methyl pantolactone: synthesis of (S)-N-Boc pipecolic acid and (S)-N-Boc-2-piperidinemethanol

  摘要：

  Racemic N-trifluoroacetyl pipecolic acid has been converted into (S)-N-Boc-pipecolic acid or (S)-N-Boc-2-piperidinemethanol by DCC/DMAP-induced diastereoselective esterification with (S)-alpha-methyl pantolactone, followed by a saponification or a reduction reaction and N-Boc protection. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00304-5

文献信息

• Diastereoselective esterification of (±)-N-trifluoroacetyl pipecolic acid using (S)-α-methyl pantolactone: synthesis of (S)-N-Boc pipecolic acid and (S)-N-Boc-2-piperidinemethanol
  作者：Monique Calmès、Françoise Escale、Marc Rolland、Jean Martinez

  DOI：10.1016/s0957-4166(03)00304-5

  日期：2003.6

  Racemic N-trifluoroacetyl pipecolic acid has been converted into (S)-N-Boc-pipecolic acid or (S)-N-Boc-2-piperidinemethanol by DCC/DMAP-induced diastereoselective esterification with (S)-alpha-methyl pantolactone, followed by a saponification or a reduction reaction and N-Boc protection. (C) 2003 Elsevier Science Ltd. All rights reserved.