(1R,2R)-N-(1-benzyloxymethyl-2-hydroxy-3-butenyl)-acetamide | 315719-02-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1R,2R)-N-(1-benzyloxymethyl-2-hydroxy-3-butenyl)-acetamide
• 英文别名: N-[(2R,3R)-3-hydroxy-1-phenylmethoxypent-4-en-2-yl]acetamide
• CAS: 315719-02-9
• 化学式: C₁₄H₁₉NO₃
• 分子量: 249.31
• InChiKey: SRQVESDICQWWJS-ZIAGYGMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,2R)-N-(1-benzyloxymethyl-2-hydroxy-3-butenyl)-acetamide 在 硫酸 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (4R,5R)-4-benzyloxymethyl-5-vinyloxazolidin-2-one
  参考文献：
  名称：

  A Regio- and Stereodivergent Route to All Isomers of vic-Amino Alcohols

  摘要：

  Vicinal amino alcohols are substructures in several important natural products. They are also frequently employed ligands in asymmetric synthesis. Many enantioselective syntheses of vic-amino alcohols have been reported, but each structure has required its own synthetic route. This study presents a synthetic strategy leading to all eight possible isomers of a given beta-amino alcohol, starting from vinyl epoxides. The developed strategy focuses on the propensity of vinyl epoxides and vinylaziridines to be selectively ring-opened at the allylic position by suitable hard nucleophiles. Within this strategy, a novel large-scale aminolysis reaction and the synthesis of a trisubstituted N-H vinylaziridine are detailed.

  DOI：

  10.1021/jo0262053
• 作为产物：
  描述：

  (2R,3R)-3-amino-1-benzyloxypent-4-en-2-ol 在 4-二甲氨基吡啶 偶氮二甲酸二异丙酯 、 三氟化硼乙醚 、 水 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 20.5h， 生成 (1R,2R)-N-(1-benzyloxymethyl-2-hydroxy-3-butenyl)-acetamide
  参考文献：
  名称：

  A Regio- and Stereodivergent Route to All Isomers of vic-Amino Alcohols

  摘要：

  Vicinal amino alcohols are substructures in several important natural products. They are also frequently employed ligands in asymmetric synthesis. Many enantioselective syntheses of vic-amino alcohols have been reported, but each structure has required its own synthetic route. This study presents a synthetic strategy leading to all eight possible isomers of a given beta-amino alcohol, starting from vinyl epoxides. The developed strategy focuses on the propensity of vinyl epoxides and vinylaziridines to be selectively ring-opened at the allylic position by suitable hard nucleophiles. Within this strategy, a novel large-scale aminolysis reaction and the synthesis of a trisubstituted N-H vinylaziridine are detailed.

  DOI：

  10.1021/jo0262053

文献信息

• A Regio- and Stereodivergent Synthesis of <i>v</i><i>ic</i>-Amino Alcohols
  作者：Berit Olofsson、Uttam Khamrai、Peter Somfai

  DOI：10.1021/ol006736i

  日期：2000.12.1

  [GRAPHICS]A regio- and stereodivergent synthesis of vic-amino alcohols starting from vinylepoxides is described. The developed strategy focuses on the propensity of vinylepoxides and vinylaziridines to be ring-opened at the allylic position by suitable nucleophiles and makes use of reactions that perform such tasks selectively with either retention or inversion of configuration.
• A Regio- and Stereodivergent Route to All Isomers of <i>v</i><i>ic</i>-Amino Alcohols
  作者：Berit Olofsson、Peter Somfai

  DOI：10.1021/jo0262053

  日期：2002.11.1

  Vicinal amino alcohols are substructures in several important natural products. They are also frequently employed ligands in asymmetric synthesis. Many enantioselective syntheses of vic-amino alcohols have been reported, but each structure has required its own synthetic route. This study presents a synthetic strategy leading to all eight possible isomers of a given beta-amino alcohol, starting from vinyl epoxides. The developed strategy focuses on the propensity of vinyl epoxides and vinylaziridines to be selectively ring-opened at the allylic position by suitable hard nucleophiles. Within this strategy, a novel large-scale aminolysis reaction and the synthesis of a trisubstituted N-H vinylaziridine are detailed.