S-2,5-dihydroxy-N-(4-methoxybenzyl)pentanamide | 908040-12-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: S-2,5-dihydroxy-N-(4-methoxybenzyl)pentanamide
• 英文别名: (S)-N-(4-methoxybenzyl)-2,5-dihydroxypentanamide；(2S)-2,5-dihydroxy-N-[(4-methoxyphenyl)methyl]pentanamide
• CAS: 908040-12-0
• 化学式: C₁₃H₁₉NO₄
• 分子量: 253.298
• InChiKey: SUWBLJYQUWNPJY-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  78.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  S-2,5-dihydroxy-N-(4-methoxybenzyl)pentanamide 在 乙酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以70%的产率得到(3S)-1-(4-methoxybenzyl)-3,6-dihydroxypiperidin-2-one
  参考文献：
  名称：

  Asymmetric syntheses of (−)-epi-pseudoconhydrine and (−)-5-hydroxysedamine based on a cis-diastereoselective 1,4-asymmetric induction

  摘要：

  The asymmetric syntheses of (-)-epi-pseudoconhydrine and (-)-5-hydroxysedamine are reported. The key to these syntheses is an unusual highly cis-diastereoselective 1,4-asymmetric induction in the alpha-amidoallylation of the new chiral building block 15. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.05.002
• 作为产物：
  描述：

  (S)-N-(4-甲氧基苄基)-四氢-5-氧代-2-呋喃甲酰胺 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以89%的产率得到S-2,5-dihydroxy-N-(4-methoxybenzyl)pentanamide
  参考文献：
  名称：

  Syntheses of enantio-enriched chiral building blocks from l-glutamic acid

  摘要：

  Starting from lactone-amide 8, easily derived from L-glutamic acid, enantioselective syntheses of (S)-tetrahydrofuran 2-carboxamide derivative 2 and a protected (S)-3-hydroxypiperidin-2-one (3) are reported. The building block 3 was converted to (2S,3R)-3-hydroxypipecolamide (6) by a three-step procedure. A solvent altered H-bonding capacity leading to a highly chemoselective tosylation of the primary hydroxyl group in the presence of an alpha-hydroxy-carboxamide was observed. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.05.013

文献信息

• Syntheses of enantio-enriched chiral building blocks from l-glutamic acid
  作者：Chen-Guo Feng、Jie Chen、Jian-Liang Ye、Yuan-Ping Ruan、Xiao Zheng、Pei-Qiang Huang

  DOI：10.1016/j.tet.2006.05.013

  日期：2006.7

  Starting from lactone-amide 8, easily derived from L-glutamic acid, enantioselective syntheses of (S)-tetrahydrofuran 2-carboxamide derivative 2 and a protected (S)-3-hydroxypiperidin-2-one (3) are reported. The building block 3 was converted to (2S,3R)-3-hydroxypipecolamide (6) by a three-step procedure. A solvent altered H-bonding capacity leading to a highly chemoselective tosylation of the primary hydroxyl group in the presence of an alpha-hydroxy-carboxamide was observed. (c) 2006 Elsevier Ltd. All rights reserved.
• Asymmetric syntheses of (−)-epi-pseudoconhydrine and (−)-5-hydroxysedamine based on a cis-diastereoselective 1,4-asymmetric induction
  作者：Gang Liu、Jie Meng、Chen-Guo Feng、Pei-Qiang Huang

  DOI：10.1016/j.tetasy.2008.05.002

  日期：2008.6

  The asymmetric syntheses of (-)-epi-pseudoconhydrine and (-)-5-hydroxysedamine are reported. The key to these syntheses is an unusual highly cis-diastereoselective 1,4-asymmetric induction in the alpha-amidoallylation of the new chiral building block 15. (C) 2008 Elsevier Ltd. All rights reserved.