N-Hydroxy-2,4,6-trimethyl-benzamidine

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-Hydroxy-2,4,6-trimethyl-benzamidine
• 英文别名: N inverted exclamation mark-Hydroxy-2,4,6-trimethylbenzimidamide；N'-hydroxy-2,4,6-trimethylbenzenecarboximidamide
• 化学式: C₁₀H₁₄N₂O
• 分子量: 178.234
• InChiKey: AYUPZKABTCADNQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-Hydroxy-2,4,6-trimethyl-benzamidine 在 四丁基氟化铵 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 5-methyl-3-(2,4,6-trimethylphenyl)-1,2,4-oxadiazole
  参考文献：
  名称：

  使用四丁基氟化铵作为温和高效的催化剂合成3,5-二取代-1,2,4-恶二唑

  摘要：

  发现四丁基氟化铵（TBAF）是合成3,5-二取代-1,2,4-恶二唑的温和而有效的催化剂。在室温下，使用THF中的0.1–1.0当量的TBAF，在室温下放置1–24小时，可以将烷酰基-和芳酰氧基am以高收率转化为相应的3,5-二取代-1,2,4-恶二唑。研究了各种R和R'取代基。

  DOI：

  10.1016/s0040-4039(00)02288-7
• 作为产物：
  描述：

  2,4,6-三甲基苯甲腈 在 羟胺 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 N-Hydroxy-2,4,6-trimethyl-benzamidine
  参考文献：
  名称：

  使用四丁基氟化铵作为温和高效的催化剂合成3,5-二取代-1,2,4-恶二唑

  摘要：

  发现四丁基氟化铵（TBAF）是合成3,5-二取代-1,2,4-恶二唑的温和而有效的催化剂。在室温下，使用THF中的0.1–1.0当量的TBAF，在室温下放置1–24小时，可以将烷酰基-和芳酰氧基am以高收率转化为相应的3,5-二取代-1,2,4-恶二唑。研究了各种R和R'取代基。

  DOI：

  10.1016/s0040-4039(00)02288-7

文献信息

• Oxygen-insensitive enzymatic reduction of oximes to imines
  作者：Sabine Heberling、Ulrich Girreser、Stephanie Wolf、Bernd Clement

  DOI：10.1016/j.bcp.2005.10.037

  日期：2006.1

  The reduction of oximes to imines under anaerobic and aerobic conditions was studied using (E)- and (Z)-2,4,6-trimethylacetophenone oxime, benzaldoxime and (E)-2,4,6-trimethylbenzaldoxime. Pig and human liver microsomes, pig liver mitochondria and cytosol to a minor extent catalyzed the conversion of both isomeric ketoximes to the corresponding stable imine, the (E)-isomer being the better substrate. All reactions were oxygen-insensitive and required active protein and NADH or NADPH; however, NADH was preferred as cofactor. The reconstituted liver microsomal system of a pig liver CYP2D enzyme (NADH-benzamidoxime reductase), which is known to reduce N-hydroxylated derivatives of strongly basic functional groups, such as amidoximes, is also capable of reducing oximes. As expected, the corresponding imine was detected in relevant amounts when incubating 2,4,6-trimethylacetophenone oxime using the reconstituted enzyme system, but reduction rates were significantly lower compared to rates obtained when incubating benzamidoxime. Steric hindrance due to the methyl groups in ortho position to the oxime functionality could be excluded as being responsible for the lower conversion rates according to results obtained in incubations of 2,4,6-trimethylbenzamidoxime. When incubating benzaldoxime, only benzoic acid could be detected as metabolite, since the alclehyde is easily oxidized during incubation procedures, whereas incubations of (E)-2,4,6-trimethylbenzaldoxime also showed the formation of the corresponding aldehyde. These results allow us to postulate that the metabolism of aldoximes like 2,4,6-trimethylbenzaldoxime most likely proceeds through enzymatic reduction of the oxime to yield the intermediate imine, which is subsequently hydrolyzed to the aldehyde and then oxidized to the corresponding benzoic acid. (c) 2005 Elsevier Inc. All rights reserved.
• Corsaro, Antonio; Chiacchio, Ugo; Perrini, Giancarlo, Journal of Chemical Research, Miniprint, 1984, # 12, p. 3449 - 3464
  作者：Corsaro, Antonio、Chiacchio, Ugo、Perrini, Giancarlo、Caramella, Pierluigi、Purrello, Giovanni

  DOI：——

  日期：——
• CORSARO, A.;CHIACCHIO, U.;PERRINI, G.;CARAMELLA, P.;PURRELLO, G., J. CHEM. RES. MICROFICHE, 1984, N 12, 402-403
  作者：CORSARO, A.、CHIACCHIO, U.、PERRINI, G.、CARAMELLA, P.、PURRELLO, G.

  DOI：——

  日期：——
• Synthesis of 3,5-disubstituted-1,2,4-oxadiazoles using tetrabutylammonium fluoride as a mild and efficient catalyst
  作者：Anthony R Gangloff、Joane Litvak、Emma J Shelton、David Sperandio、Vivian R Wang、Kenneth D Rice

  DOI：10.1016/s0040-4039(00)02288-7

  日期：2001.2

  Tetrabutylammonium fluoride (TBAF) was found to be a mild and efficient catalyst for the synthesis of 3,5-disubstituted-1,2,4-oxadiazoles. Using 0.1–1.0 equivalents of TBAF in THF for 1–24 h at room temperature, alkanoyl- and aroyloxyamidines were converted in high yield to the corresponding 3,5-disubstituted-1,2,4-oxadiazoles. A variety of R and R′ substituents were investigated.

  发现四丁基氟化铵（TBAF）是合成3,5-二取代-1,2,4-恶二唑的温和而有效的催化剂。在室温下，使用THF中的0.1–1.0当量的TBAF，在室温下放置1–24小时，可以将烷酰基-和芳酰氧基am以高收率转化为相应的3,5-二取代-1,2,4-恶二唑。研究了各种R和R'取代基。