(E)-(R)-(+)-O-(1-phenylbutyl)-5-methyl-2-furaldoxime | 230311-05-4

• 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: (E)-(R)-(+)-O-(1-phenylbutyl)-5-methyl-2-furaldoxime
• 英文别名: (E)-1-(5-methylfuran-2-yl)-N-[(1R)-1-phenylbutoxy]methanimine
• CAS: 230311-05-4
• 化学式: C₁₆H₁₉NO₂
• 分子量: 257.332
• InChiKey: HWTIDBDEDNYAEI-QRYYFKOISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  34.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  甲基锂 、 (E)-(R)-(+)-O-(1-phenylbutyl)-5-methyl-2-furaldoxime 在 三氟化硼乙醚 作用下， 生成 (1S,1'R)-N-(1-phenylbutoxy)-5-(2-methylfuryl)-1-ethylamine 、 (1R,1'R)-(+)-N-(1-phenylbutoxy)-5-(2-methylfuryl)-1-ethylamine
  参考文献：
  名称：

  Chiral Oxime Ethers in Asymmetric Synthesis. 3.¹ Asymmetric Synthesis of (R)-N-Protected α-Amino Acids by the Addition of Organometallic Reagents to the ROPHy Oxime of Cinnamaldehyde

  摘要：

  A new asymmetric synthesis of a-amino acids is described in which the key step is the diastereoselective addition of organometallic reagents to (R)-O-(1-phenylbutyl)cinnamaldoxime 5 to give hydroxylamines 6. Subsequent reductive cleavage of the N-O bond in the hydroxylamine 6 followed by N-protection gave the carbamates 7, which upon oxidation with ruthenium(III) chloride/periodate gave the N-protected amino acids 8. The method was also adapted to the synthesis of a quaternary amino acid 15 from the ketoxime ether 9.

  DOI：

  10.1021/jo9901079
• 作为产物：
  描述：

  5-甲基呋喃醛 、 (R)-(+)-N-(1-phenylbutoxy)phthalimide 在 一水合肼 作用下， 生成 (Z)-(R)-(+)-O-(1-phenylbutyl)-5-methyl-2-furaldoxime 、 (E)-(R)-(+)-O-(1-phenylbutyl)-5-methyl-2-furaldoxime
  参考文献：
  名称：

  Chiral Oxime Ethers in Asymmetric Synthesis. 3.¹ Asymmetric Synthesis of (R)-N-Protected α-Amino Acids by the Addition of Organometallic Reagents to the ROPHy Oxime of Cinnamaldehyde

  摘要：

  A new asymmetric synthesis of a-amino acids is described in which the key step is the diastereoselective addition of organometallic reagents to (R)-O-(1-phenylbutyl)cinnamaldoxime 5 to give hydroxylamines 6. Subsequent reductive cleavage of the N-O bond in the hydroxylamine 6 followed by N-protection gave the carbamates 7, which upon oxidation with ruthenium(III) chloride/periodate gave the N-protected amino acids 8. The method was also adapted to the synthesis of a quaternary amino acid 15 from the ketoxime ether 9.

  DOI：

  10.1021/jo9901079

文献信息

• Chiral Oxime Ethers in Asymmetric Synthesis. 3.¹ Asymmetric Synthesis of (<i>R</i>)-N-Protected α-Amino Acids by the Addition of Organometallic Reagents to the ROPHy Oxime of Cinnamaldehyde
  作者：Christopher J. Moody、Peter T. Gallagher、Andrew P. Lightfoot、Alexandra M. Z. Slawin

  DOI：10.1021/jo9901079

  日期：1999.6.1

  A new asymmetric synthesis of a-amino acids is described in which the key step is the diastereoselective addition of organometallic reagents to (R)-O-(1-phenylbutyl)cinnamaldoxime 5 to give hydroxylamines 6. Subsequent reductive cleavage of the N-O bond in the hydroxylamine 6 followed by N-protection gave the carbamates 7, which upon oxidation with ruthenium(III) chloride/periodate gave the N-protected amino acids 8. The method was also adapted to the synthesis of a quaternary amino acid 15 from the ketoxime ether 9.