ethyl 8-hydroxyiminooctanoate (syn)

• 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 (syn)
• 英文别名: ethyl (8E)-8-(hydroxyimino)octanoate；ethyl (8E)-8-hydroxyiminooctanoate
• 化学式: C₁₀H₁₉NO₃
• 分子量: 201.266
• InChiKey: XHXWZCVGNWURLH-PKNBQFBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  58.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  8-溴辛酸乙酯 在 吡啶 、 盐酸羟胺 、 sodium carbonate 、 二甲基亚砜 、 potassium iodide 作用下， 以 乙醇 为溶剂， 反应 13.5h， 生成 ethyl 8-hydroxyiminooctanoate (syn)
  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

文献信息

• MOORHOFF, CORNELIS M.;PAQUETTE, LEO A., J. ORG. CHEM., 56,(1991) N, C. 703-710
  作者：MOORHOFF, CORNELIS M.、PAQUETTE, LEO A.

  DOI：——

  日期：——
• Synthesis, analysis and rearrangement of novel unnatural glucosinolates
  作者：Nicola E. Davidson、Trevor J. Rutherford、Nigel P. Botting

  DOI：10.1016/s0008-6215(00)00308-6

  日期：2001.2

  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.