chloro-1-naphthylacetaldoxime | 340960-73-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: chloro-1-naphthylacetaldoxime
• 英文别名: N-hydroxy-2-naphthalen-1-ylethanimidoyl chloride
• CAS: 340960-73-8
• 化学式: C₁₂H₁₀ClNO
• 分子量: 219.671
• InChiKey: IMBJXEMHGZQQSL-UHFFFAOYSA-N

物化性质

• 沸点：
  412.7±38.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  32.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  chloro-1-naphthylacetaldoxime 在 吡啶 、 氯磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成
  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：

  1-naphthylacetaldoxime 在 N-氯代丁二酰亚胺 作用下， 以 吡啶 、 氯仿 为溶剂， 反应 4.0h， 以48%的产率得到chloro-1-naphthylacetaldoxime
  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

• A simple O-sulfated thiohydroximate molecule to be the first micromolar range myrosinase inhibitor
  作者：Deimante Cerniauskaite、Estelle Gallienne、Henreta Karciauskaite、Andrea S.F. Farinha、Jolanta Rousseau、Sylvie Armand、Arnaud Tatibouët、Algirdas Sackus、Patrick Rollin

  DOI：10.1016/j.tetlet.2009.02.072

  日期：2009.7

  New non-hydrolyzable analogues of glucosinolates have been prepared. Myrosinase inhibition was observed with modified aglycon moieties, even bulky phenothiazine analogue 6 gave reasonable inhibition. The simplest structure 8 derived from dimethylaminoethanethiol has shown to be the most potent inhibitor with an IC50 of 3.32 mu M. (C) 2009 Elsevier Ltd. All rights reserved.