(2R,3S)-2-amino-6-benzyloxy-4(E)-hexen-3-ol | 596129-38-3

• 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: (2R,3S)-2-amino-6-benzyloxy-4(E)-hexen-3-ol
• 英文别名: (2R,3S)-2-Amino-6-(benzyloxy)-4-hexene-3-ol；(E,2R,3S)-2-amino-6-phenylmethoxyhex-4-en-3-ol
• CAS: 596129-38-3
• 化学式: C₁₃H₁₉NO₂
• 分子量: 221.299
• InChiKey: REUBOAVPEPKODT-XPDZNBDNSA-N

物化性质

• 沸点：
  366.1±42.0 °C(Predicted)
• 密度：
  1.070±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  55.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,3S)-2-amino-6-benzyloxy-4(E)-hexen-3-ol 在 双氧水 、 一水合肼 作用下， 以 乙醇 为溶剂， 生成 (2R,3S)-2-Amino-6-benzyloxy-hexan-3-ol
  参考文献：
  名称：

  Determination of the relative configuration of vic-amino alcohols

  摘要：

  A large set of syn- and anti-1,2-amino alcohols has been synthesized. Upon comparison of the CHO and CHN H-1 NMR shifts a general trend has been observed, making it possible to determine the relative configuration of 1,2-amino alcohols without derivatization or shift reagents. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02787-9
• 作为产物：
  描述：

  (2E,4E)-2,4-己二烯-1-醇 在 C₆H₆O₆(C₃H₆)2 Sodium tetraborate decahydrate 、 Oxone 、 ammonium hydroxide 、 高氯酸 、 偶氮二甲酸二异丙酯 、 polymer-bound PPh₃ 、 四丁基硫酸氢铵 、 sodium hydride 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 44.67h， 生成 (2R,3S)-2-amino-6-benzyloxy-4(E)-hexen-3-ol
  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 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.
• Determination of the relative configuration of vic-amino alcohols
  作者：Berit Olofsson、Peter Somfai

  DOI：10.1016/s0040-4039(02)02787-9

  日期：2003.2

  A large set of syn- and anti-1,2-amino alcohols has been synthesized. Upon comparison of the CHO and CHN H-1 NMR shifts a general trend has been observed, making it possible to determine the relative configuration of 1,2-amino alcohols without derivatization or shift reagents. (C) 2003 Elsevier Science Ltd. All rights reserved.