(3E,2R,αR)-2-(N-benzyl-N-α-methylbenzylamino)pent-3-enal | 487042-27-3

• 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: (3E,2R,αR)-2-(N-benzyl-N-α-methylbenzylamino)pent-3-enal
• 英文别名: (E,2R)-2-[benzyl-[(1R)-1-phenylethyl]amino]pent-3-enal
• CAS: 487042-27-3
• 化学式: C₂₀H₂₃NO
• 分子量: 293.409
• InChiKey: BXJVPHNEDOATOY-TWNLFCHXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3E,2R,αR)-2-(N-benzyl-N-α-methylbenzylamino)pent-3-enal 在 sodium chlorite 、 环己烯 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 (3E,2R,αR)-2-(N-benzyl-N-α-methylbenzylamino)pent-3-enoic acid
  参考文献：
  名称：

  Asymmetric synthesis of α-amino carbonyl derivatives using lithium (R)-N-benzyl-N-α-methylbenzylamide

  摘要：

  An efficient protocol for the transformation of homochiral alpha-hydroxy-beta-amino esters to their alpha-amino carbonyl components is presented. Diastereoselective conjugate addition of lithium (R)-N-benzyl-N-alpha-methylbenzylamide to a range of alpha,beta-unsaturated esters and subsequent enolate hydroxylation with (1R)-(-)-(camphorsulfonyl)oxaziridine, followed by LiAlH4 reduction produces homochiral 3-amino-1,2-diols. Subsequent oxidative cleavage with H5IO6 provides N-benzyl-N-alpha-methylbenzyl protected alpha-amino aldehydes (96-98% d.e.) and ketones (88% d.e.). Further oxidation of the alpha-amino aldehydes with sodium chlorite and Pd-catalysed hydrogenation provides alpha-amino acids in 94-98% e.e. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00406-8
• 作为产物：
  描述：

  tert-butyl (2E,4E)-2,4-hexadienoate 在 lithium aluminium tetrahydride 、 正丁基锂 、 高碘酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 38.5h， 生成 (3E,2R,αR)-2-(N-benzyl-N-α-methylbenzylamino)pent-3-enal
  参考文献：
  名称：

  Asymmetric synthesis of α-amino carbonyl derivatives using lithium (R)-N-benzyl-N-α-methylbenzylamide

  摘要：

  An efficient protocol for the transformation of homochiral alpha-hydroxy-beta-amino esters to their alpha-amino carbonyl components is presented. Diastereoselective conjugate addition of lithium (R)-N-benzyl-N-alpha-methylbenzylamide to a range of alpha,beta-unsaturated esters and subsequent enolate hydroxylation with (1R)-(-)-(camphorsulfonyl)oxaziridine, followed by LiAlH4 reduction produces homochiral 3-amino-1,2-diols. Subsequent oxidative cleavage with H5IO6 provides N-benzyl-N-alpha-methylbenzyl protected alpha-amino aldehydes (96-98% d.e.) and ketones (88% d.e.). Further oxidation of the alpha-amino aldehydes with sodium chlorite and Pd-catalysed hydrogenation provides alpha-amino acids in 94-98% e.e. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00406-8

文献信息

• Asymmetric synthesis of α-amino carbonyl derivatives using lithium (R)-N-benzyl-N-α-methylbenzylamide
  作者：Stephen G. Davies、Simon W. Epstein、A.Christopher Garner、Osamu Ichihara、Andrew D. Smith

  DOI：10.1016/s0957-4166(02)00406-8

  日期：2002.8

  An efficient protocol for the transformation of homochiral alpha-hydroxy-beta-amino esters to their alpha-amino carbonyl components is presented. Diastereoselective conjugate addition of lithium (R)-N-benzyl-N-alpha-methylbenzylamide to a range of alpha,beta-unsaturated esters and subsequent enolate hydroxylation with (1R)-(-)-(camphorsulfonyl)oxaziridine, followed by LiAlH4 reduction produces homochiral 3-amino-1,2-diols. Subsequent oxidative cleavage with H5IO6 provides N-benzyl-N-alpha-methylbenzyl protected alpha-amino aldehydes (96-98% d.e.) and ketones (88% d.e.). Further oxidation of the alpha-amino aldehydes with sodium chlorite and Pd-catalysed hydrogenation provides alpha-amino acids in 94-98% e.e. (C) 2002 Elsevier Science Ltd. All rights reserved.