4-hydroxybutanal O-methyloxime

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-hydroxybutanal O-methyloxime
• 英文别名: (4Z)-4-methoxyiminobutan-1-ol
• 化学式: C₅H₁₁NO₂
• 分子量: 117.148
• InChiKey: OSZXQFZIJCNDBO-XQRVVYSFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  8
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  41.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  四氢呋喃 、 3-氯苯甲酰乙腈 在 air 、 Dimethylzinc 作用下， 以 正己烷 为溶剂， 反应 120.0h， 生成 4-hydroxybutanal O-methyloxime 、 4-hydroxybutanal O-methyloxime
  参考文献：
  名称：

  Dimethylzinc-initiated radical reaction of cyclic ethers with arylamines, alkoxyamines, and dialkylhydrazines

  摘要：

  Dimethylzinc-initiated radical reaction of THF with arylamines afforded aminoalcohols which were derived from the two molecules of THF and one molecule of an arylamine. The reaction seems to proceed via two-consecutive processes, electrophilic and then nucleophilic reactions of THF-derived species. Alkoxyamines and dialkylhydrazines reacted with electrophilic cyclic ether species to give the corresponding oximes and hydrazones of omega-hydroxyalkanal. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.10.080

文献信息

• Oxime ether analogs of sex pheromone components of turnip moth (Agrotis segetum Schiffermüller)
  作者：D. Martin、B. Weber

  DOI：10.1007/bf02059743

  日期：1994.5

  Oxime ether analogs of sex pheromone components of the turnip moth (Agrotis segetum Schiff.) were synthesized by the acidolytic opening of cyclic enol ethers with O-alkyl hydroxylamine hydrochlorides. The compounds varying in chain lengths and in the position of the C=N double bond were studied by electrophysiological single sensillum recordings (electrosensillography: ESG). The ESG data indicate in general reduced receptor interaction of all analogs investigated in comparison with natural pheromone components of the turnip moth. The data also show that the grade of decrease of receptor interaction depends on specific structural changes within the molecule. The results demonstrate high complementary pheromone-receptor relationships, predominantly depending on the position of the unsaturated group in the chain, whereas analogs with other structural changes are still recognized as a pheromone-like compound by the receptor.
• Dimethylzinc-initiated radical reaction of cyclic ethers with arylamines, alkoxyamines, and dialkylhydrazines
  作者：Yasutomo Yamamoto、Masaru Maekawa、Tito Akindele、Ken-ichi Yamada、Kiyoshi Tomioka

  DOI：10.1016/j.tet.2004.10.080

  日期：2005.1

  Dimethylzinc-initiated radical reaction of THF with arylamines afforded aminoalcohols which were derived from the two molecules of THF and one molecule of an arylamine. The reaction seems to proceed via two-consecutive processes, electrophilic and then nucleophilic reactions of THF-derived species. Alkoxyamines and dialkylhydrazines reacted with electrophilic cyclic ether species to give the corresponding oximes and hydrazones of omega-hydroxyalkanal. (C) 2004 Elsevier Ltd. All rights reserved.