1,3-dioxolane-2,2-dimethyl-4-acetaldehyde oxime | 152775-85-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3-dioxolane-2,2-dimethyl-4-acetaldehyde oxime
• 英文别名: N-[2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethylidene]hydroxylamine
• CAS: 152775-85-4
• 化学式: C₇H₁₃NO₃
• 分子量: 159.185
• InChiKey: RSMAIBPPUNGKFS-UHFFFAOYSA-N

物化性质

• 沸点：
  254.1±15.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  51
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,3-dioxolane-2,2-dimethyl-4-acetaldehyde oxime 在 镍 吡啶 、 N-氯代丁二酰亚胺 、 氢气 、 三乙胺 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 0.83h， 生成 5-(2,2-Dimethyl-[1,3]dioxolan-4-yl)-2-hydroxy-4-oxo-pentanoic acid methyl ester
  参考文献：
  名称：

  Synthesis of melodienone and 7-hydroxy-6-hydromelodienone, two heptenes from Melodorum fruticosum.

  摘要：

  An unified approach to the construction of the seven carbon atom framework of the title compounds having a gamma-oxoacrylate moiety as common structural feature, utilizing an intermolecular [3+2] cycloaddition of the nitrile oxide generated from a malic acid derived C-4 aldehyde fragment with methyl acrylate, is described.

  DOI：

  10.1016/s0040-4020(01)89589-2
• 作为产物：
  描述：

  2-(2,2-dimethyl-1,3-dioxolan-4-yl)acetaldehyde 在 盐酸羟胺 、 碳酸氢钠 作用下， 以 乙醇 、 水 为溶剂， 以65%的产率得到1,3-dioxolane-2,2-dimethyl-4-acetaldehyde oxime
  参考文献：
  名称：

  Synthesis of melodienone and 7-hydroxy-6-hydromelodienone, two heptenes from Melodorum fruticosum.

  摘要：

  An unified approach to the construction of the seven carbon atom framework of the title compounds having a gamma-oxoacrylate moiety as common structural feature, utilizing an intermolecular [3+2] cycloaddition of the nitrile oxide generated from a malic acid derived C-4 aldehyde fragment with methyl acrylate, is described.

  DOI：

  10.1016/s0040-4020(01)89589-2

文献信息

• Antipicornavirus activity of tetrazole analogs related to disoxaril
  作者：Guy D. Diana、David Cutcliffe、Deborah L. Volkots、John P. Mallamo、Thomas R. Bailey、Niranjan Vescio、Richard C. Oglesby、Theodore J. Nitz、Joseph Wetzel

  DOI：10.1021/jm00074a004

  日期：1993.10

  A series of tetrazole analogues of Win 54954, a broad-spectrum antipicornavirus compound, has been synthesized to address the acid lability of the oxazoline ring of this series of compounds. The results of X-ray crystallography studies of several members of the oxazoline series bound to human rhinovirus type IA and 14 have been used to design compounds in the tetrazole series with a broad spectrum of activity. Compound 16b, which has a three-carbon linkage between the isoxazole and phenyl rings and a propyl chain extending from the isoxazole ring, exhibiting an MIC80 for 15 rhinovirus serotypes of 0.20 muM as compared to 0.40 muM for Win 54954. X-ray studies of 16b bound to human rhinovirus-14 show that the propyl side chain extends into a pore in the binding site with the possibility of hydrophobic interactions with a pocket formed by Leu106 and a portion of Ser107.