2-acetamido-2-deoxy-D-arabinono-1,4-lactone | 117771-16-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-acetamido-2-deoxy-D-arabinono-1,4-lactone
• 英文别名: N-[(3S,4S,5R)-4-hydroxy-5-(hydroxymethyl)-2-oxooxolan-3-yl]acetamide
• CAS: 117771-16-1
• 化学式: C₇H₁₁NO₅
• 分子量: 189.168
• InChiKey: SFSOCLFOPIFBBR-NGJCXOISSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  95.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-acetamido-2-deoxy-D-arabinono-1,4-lactone 、 乙酸酐 生成 [(2R,3S,4S)-4-acetamido-3-hydroxy-5-oxooxolan-2-yl]methyl acetate
  参考文献：
  名称：

  BOLS, MIKAEL;LUNDT, INGE, ACTA CHEM. SCAND., 42,(1988) N 2, 67-74

  摘要：

  DOI：
• 作为产物：
  描述：

  2-acetamido-2-deoxy-D-arabinose N,N'-diphenylformazan 在 三氟乙酸 作用下， 以 乙醇 为溶剂， 生成 2-acetamido-2-deoxy-D-arabinono-1,4-lactone
  参考文献：
  名称：

  Corrigendum to ‘‘Transformation of aldose formazans. Novel synthesis of 2-acetamido-2-deoxypentonolactones and a new pent-2-enose formazan” [Carbohydr. Res. 346 (2011) 1534–1540]

  摘要：

  DOI：

  10.1016/j.carres.2011.09.023

文献信息

• Bols, Mikael; Lundt, Inge, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1988, vol. 42, # 2, p. 67 - 74
  作者：Bols, Mikael、Lundt, Inge

  DOI：——

  日期：——
• Transformation of aldose formazans. Novel synthesis of 2-acetamido-2-deoxypentonolactones and a new pent-2-enose formazan
  作者：Virág Zsoldos-Mády、István Pintér、Mária Peredy-Kajtár、András Perczel

  DOI：10.1016/j.carres.2011.04.026

  日期：2011.9

  2-Acetamido-2-deoxypentonolactones were synthesized from per-O-acetylated formazans of D-ribose, D- and L-arabinose, respectively. In dimethyl sulfoxide, a novel spontaneous transformation of the per-O-acetyl-pentose formazans into new 3,4,5-tri-O-acetyl-pent-2-enose formazans has been recognized. Additional examples for the occurrence of the isomerism between pseudo-aromatic chelate and open phenylazo-phenylhydrazone system were demonstrated by (1)H NMR spectroscopy in both the unprotected pentose formazans and 3,4,5-tri-O-acetyl-pent-2-enose formazans. Computational calculations supported higher stability of the ring form. (C) 2011 Elsevier Ltd. All rights reserved.