(2R,3R,αR)-2-hydroxy-3-(N-benzyl-N-α-methylbenzyl)aminodecanol | 487042-17-1

• 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,3R,αR)-2-hydroxy-3-(N-benzyl-N-α-methylbenzyl)aminodecanol
• 英文别名: (2R,3R)-3-[benzyl-[(1R)-1-phenylethyl]amino]decane-1,2-diol
• CAS: 487042-17-1
• 化学式: C₂₅H₃₇NO₂
• 分子量: 383.574
• InChiKey: WAJPGPJAEWPJCU-SDUSCBPUSA-N

物化性质

• 沸点：
  528.8±30.0 °C(Predicted)
• 密度：
  1.041±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  28
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  43.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,3R,αR)-2-hydroxy-3-(N-benzyl-N-α-methylbenzyl)aminodecanol 在 高碘酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以92%的产率得到(2R,αR)-2-(N-benzyl-N-α-methylbenzylamino)nonanal
  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：

  trans-2-decenoic acid tert-butyl ester 在 lithium aluminium tetrahydride 、 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 38.0h， 生成 (2R,3R,αR)-2-hydroxy-3-(N-benzyl-N-α-methylbenzyl)aminodecanol
  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.