ethyl 8-hydroxyiminooctanoate | 42586-36-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 8-hydroxyiminooctanoate
• CAS: 42586-36-7
• 化学式: C₁₀H₁₉NO₃
• 分子量: 201.266
• InChiKey: XHXWZCVGNWURLH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.35
• 重原子数：
  14.0
• 可旋转键数：
  8.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  58.89
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ethyl 8-hydroxyiminooctanoate 在 N-氯代丁二酰亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 吡啶 、 氯仿 为溶剂， 反应 3.5h， 生成 ethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(7-etoxycarbonylheptyl) thiohydroximate
  参考文献：
  名称：

  Synthesis, analysis and rearrangement of novel unnatural glucosinolates

  摘要：

  As part of a structure activity study to examine the interaction of glucosinolates with leaf surfaces,a number of glucosinolates were synthesised bearing novel side chain functionalities. These included 7-carboxyheptyl, heptyl, and naphthyl side chains. For the carboxyheptyl glucosinolate, a novel intramolecular rearrangement reaction was observed during the final deprotection step, which generated an ester attached to the C-3 of glucose. Studies by H-1 NMR spectroscopy showed that the hydrophobic side chain associated with one face of the glucose ring and it was proposed that this was the driving force for the rearrangement. Similar hydrophobic interactions were also observed between the heptyl and naphthyl side chains and the glucose. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00308-6
• 作为产物：
  描述：

  环辛酮 、 亚硝酸乙酯 在 正丁基锂 、 二异丙胺 作用下， 生成 ethyl 8-hydroxyiminooctanoate
  参考文献：
  名称：

  Isodicyclopentadienes and related molecules. 53. Unsymmetrical oxidative cleavage of cyclic ketones. Conversion to .omega.-ethoxycarbonyl aldoximes under alkaline conditions

  摘要：

  A useful procedure for effecting the direct unsymmetrical cleavage of an enolizable cyclic ketone to an oximino ester has been developed. The process begins by deprotonation with LDA and is followed by the addition of ethyl nitrite in THF at low temperature. Rapid reaction customarily ensues with resultant overall nitrosolysis. Of particular importance is the facile application of this procedure to substrate ketones that are otherwise sensitive to acidic environments. This feature is exemplified in particular in the case of syn- and anti-sesquinorbornenones 34 and 35, access to which is described for the first time. Since the entire process is executed in a single flask, the methodology is very convenient to implement in practice.

  DOI：

  10.1021/jo00002a040