(2R)-2-[(3aS,6aR)-3a,4,6,6a-tetrahydro-3H-furo[3,4-c][1,2]oxazol-1-yl]-2-phenylethanol | 623582-46-7

• 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)-2-[(3aS,6aR)-3a,4,6,6a-tetrahydro-3H-furo[3,4-c][1,2]oxazol-1-yl]-2-phenylethanol
• CAS: 623582-46-7
• 化学式: C₁₃H₁₇NO₃
• 分子量: 235.283
• InChiKey: SMRSJKSLAXELOD-AVGNSLFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  41.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R)-2-[(3aS,6aR)-3a,4,6,6a-tetrahydro-3H-furo[3,4-c][1,2]oxazol-1-yl]-2-phenylethanol 在 palladium dihydroxide 氢气 、 碳酸氢钠 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 生成 Benzyl ((3R,4R)-4-(hydroxymethyl)tetrahydrofuran-3-yl)carbamate
  参考文献：
  名称：

  Synthesis of Cyclic and Acyclic β-Amino Acids via Chelation-Controlled 1,3-Dipolar Cycloaddition

  摘要：

  Isoxazolidines have been synthesized in diastereomeric excess up to 94% via a MgBr2-induced chelation-controlled 1,3-dipolar cycloaddition reaction with N-hydroxyphenylglycinol as a chiral auxiliary. The diastereomerically pure isoxazolidines were further transformed into cyclic and acyclic beta-amino acid derivatives.

  DOI：

  10.1021/jo034940o
• 作为产物：
  描述：

  2-(烯丙氧基)乙醛 、 (R)-α-(hydroxymethyl)benzylhydroxylamine 在 异丙醇 、 magnesium bromide 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以89%的产率得到(2R)-2-[(3aS,6aR)-3a,4,6,6a-tetrahydro-3H-furo[3,4-c][1,2]oxazol-1-yl]-2-phenylethanol
  参考文献：
  名称：

  Synthesis of Cyclic and Acyclic β-Amino Acids via Chelation-Controlled 1,3-Dipolar Cycloaddition

  摘要：

  Isoxazolidines have been synthesized in diastereomeric excess up to 94% via a MgBr2-induced chelation-controlled 1,3-dipolar cycloaddition reaction with N-hydroxyphenylglycinol as a chiral auxiliary. The diastereomerically pure isoxazolidines were further transformed into cyclic and acyclic beta-amino acid derivatives.

  DOI：

  10.1021/jo034940o

文献信息

• Synthesis of Cyclic and Acyclic β-Amino Acids via Chelation-Controlled 1,3-Dipolar Cycloaddition
  作者：Roger Hanselmann、Jiacheng Zhou、Philip Ma、Pat N. Confalone

  DOI：10.1021/jo034940o

  日期：2003.10.1

  Isoxazolidines have been synthesized in diastereomeric excess up to 94% via a MgBr2-induced chelation-controlled 1,3-dipolar cycloaddition reaction with N-hydroxyphenylglycinol as a chiral auxiliary. The diastereomerically pure isoxazolidines were further transformed into cyclic and acyclic beta-amino acid derivatives.