N-<(S)-2-phenylethyl>-(2S,4R)-4-hydroxypipecolic acid tert-butylamide | 175476-94-5

• 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: N-<(S)-2-phenylethyl>-(2S,4R)-4-hydroxypipecolic acid tert-butylamide
• 英文别名: (2S,4R)-N-tert-butyl-4-hydroxy-1-[(1S)-1-phenylethyl]piperidine-2-carboxamide
• CAS: 175476-94-5
• 化学式: C₁₈H₂₈N₂O₂
• 分子量: 304.433
• InChiKey: MMRAEKBTCDNFHZ-IMJJTQAJSA-N

物化性质

• 沸点：
  488.4±45.0 °C(Predicted)
• 密度：
  1.088±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  52.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-<(S)-2-phenylethyl>-(2S,4R)-4-hydroxypipecolic acid tert-butylamide 在 盐酸 、 aluminum oxide 、 氢气 、 sodium hydride 作用下， 15.0~50.0 ℃ 、101.33 kPa 条件下， 反应 29.0h， 生成 (2S,4R)-1-[(2R,3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-tert-butyl-4-(pyridin-4-ylmethoxy)piperidine-2-carboxamide
  参考文献：
  名称：

  Practical, Stereoselective Synthesis of Palinavir, a Potent HIV Protease Inhibitor

  摘要：

  Palinavir is a potent peptidomimetic-based HIV protease inhibitor. We have developed a highly convergent and stereoselective synthesis which is amenable to the preparation of multikilogram quantities of this compound. The synthetic sequence proceeds in 24 distinct chemical steps (with several integrated, multistep operations) from commercially available starting materials. No chromatographies are required throughout the process, and the final product is purified by crystallization of its dihydrochloride salt to >99% homogeneity.

  DOI：

  10.1021/jo9702655
• 作为产物：
  描述：

  N-(3-butenyl)-N-[(S)-1-phenylethyl]amine 在 异丙基氯化镁 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 17.0h， 生成 N-<(S)-2-phenylethyl>-(2S,4R)-4-hydroxypipecolic acid tert-butylamide
  参考文献：
  名称：

  Preparation of (2S,4R)-4-Hydroxypipecolic Acid and Derivatives

  摘要：

  DOI：

  10.1021/jo9519874

文献信息

• Preparation of (2<i>S</i>,4<i>R</i>)-4-Hydroxypipecolic Acid and Derivatives
  作者：James Gillard、Abraham、Paul C. Anderson、Pierre L. Beaulieu、Tibor Bogri、Yves Bousquet、Louis Grenier、Ingrid Guse、Pierre Lavallée

  DOI：10.1021/jo9519874

  日期：1996.1.1
• Practical, Stereoselective Synthesis of Palinavir, a Potent HIV Protease Inhibitor
  作者：Pierre L. Beaulieu、Pierre Lavallée、Abraham、Paul C. Anderson、Colette Boucher、Yves Bousquet、Jean-Simon Duceppe、James Gillard、Vida Gorys、Chantal Grand-Maître、Louis Grenier、Yvan Guindon、Ingrid Guse、Louis Plamondon、François Soucy、Serge Valois、Dominik Wernic、Christiane Yoakim

  DOI：10.1021/jo9702655

  日期：1997.5.1

  Palinavir is a potent peptidomimetic-based HIV protease inhibitor. We have developed a highly convergent and stereoselective synthesis which is amenable to the preparation of multikilogram quantities of this compound. The synthetic sequence proceeds in 24 distinct chemical steps (with several integrated, multistep operations) from commercially available starting materials. No chromatographies are required throughout the process, and the final product is purified by crystallization of its dihydrochloride salt to >99% homogeneity.