4-methylbenzaldehyde-O-methyl oxime | 33499-39-7

• 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: 4-methylbenzaldehyde-O-methyl oxime
• 英文别名: 4-Methyl-benzaldehyde O-methyl-oxime；p-Methylbenzaldoxim-O-methylether；O-Methyl-p-tolualdoxime；N-methoxy-1-(4-methylphenyl)methanimine
• CAS: 33499-39-7；70286-36-1；87861-02-7
• 化学式: C₉H₁₁NO
• 分子量: 149.192
• InChiKey: UCYSOTAMOJUSJH-UHFFFAOYSA-N

物化性质

• 保留指数：
  1320

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-methylbenzaldehyde-O-methyl oxime 在 盐酸 、 吡啶硼烷 作用下， 以 乙醇 、 水 为溶剂， 以3.29 g的产率得到O-methyl-N-(4-methylbenzyl)hydroxylamine
  参考文献：
  名称：

  Synthesis and biological evaluation of RON-neoglycosides as tumor cytotoxins

  摘要：

  Cardenolides such as digitoxin have been shown to inhibit cancer cell growth, to reduce cancer metastasis, and to induce apoptosis in tumor cells. Among the most potent digitoxin-based cytotoxins identified to date are MeON-neoglycosides generated via oxyamine neoglycosylation. Here, we report our studies of oxyamine neoglycosylation aimed at facilitating the elucidation of linkage-diversified digitoxin neoglycoside structure-activity relationships. We identified conditions suitable for the convenient synthesis of digitoxin neoglycosides and found that sugar structure, rather than RON-glycosidic linkage, exerts the strongest influence on neoglycoside yield and stereochemistry. We synthesized a library of digitoxin neoglycosides and assessed their cytotoxicity against eight human cancer cell lines. Consistent with previous findings, our data show that the structure of RON-neoglycosidic linkages influences both the potency and selectivity of digitoxin neoglycosides. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.09.019
• 作为产物：
  描述：

  N-甲氧基苯甲酰胺 、 对甲基苯甲醛 在 dipotassium peroxodisulfate 作用下， 以 甲醇 为溶剂， 反应 20.0h， 以74%的产率得到4-methylbenzaldehyde-O-methyl oxime
  参考文献：
  名称：

  一种基于C-N键的断裂来合成肟醚类化合物 的方法

  摘要：

  本发明涉及一种基于C‑N键的断裂来合成肟醚类化合物的方法，该方法包括将反应式(1)的化合物与反应式(2)的化合物在过氧化物、有机溶剂条件下反应，制得式(3)肟醚类化合物，其反应通式如下：本发明方法的合成路线短、起始原料简单、反应条件温和、过氧化物价廉无污染，底物范围广，产物易分离,并且当扩大到克级的反应的时候，我们的反应也能得到很好的适用性。

  公开号：

  CN106187816B

文献信息

• Novel Catalytic Three-Component Reaction between a Terminal Alkyne, Sulfonyl Azide, and O-Methyl Oxime
  作者：Mehdi Khalaj、Majid Ghazanfarpour-Darjani、Forugh Barat-Seftejani、Azita Nouri

  DOI：10.1055/s-0036-1588989

  日期：2017.7

  O-Methyl oximes have been employed as nucleophiles in reactions with ketenimines derived from sulfonyl azides and terminal alkynes to form N-alkylidene N′-tosylacetimidamide derivatives. The optimized conditions involved the use of CuPF6 and i-Pr2NEt in MeCN at 65 °C. Both O-methyl aldoximes and ketoximes were tolerated under the optimum conditions.

  O-甲基肟已被用作亲核试剂与衍生自磺酰叠氮化物和末端炔烃的烯酮亚胺反应以形成 N-亚烷基 N'-甲苯磺酰乙酰亚胺衍生物。优化条件包括在 65 °C 下在 MeCN 中使用 CuPF6 和 i-Pr2NEt。在最佳条件下，O-甲基醛肟和酮肟均可耐受。
• HIV Integrase inhibitors
  申请人：——

  公开号：US20030176495A1

  公开（公告）日：2003-09-18

  The present invention relates to the inhibition of HIV integrase, and to the treatment of AIDS or ARC by administering compounds of the following formula, or a tautomer of said compound, or a pharmaceutically acceptable salt, solvate or prodrug thereof: 1 wherein R 1 , R 2 and B 1 are as defined herein.

  本发明涉及抑制HIV整合酶，以及通过给予以下化合物、该化合物的互变异构体、或其药学上可接受的盐、溶剂化合物或前药来治疗艾滋病或ARC的方法：1其中R1、R2和B1如本文所定义。
• Preparation of dihomoallylic secondary amines through samarium mediated allylation of oximes
  作者：Xuesen Fan、Yongmin Zhang

  DOI：10.1016/s0040-4039(02)01042-0

  日期：2002.7

  Allylsamarium bromide adds to oximes derived from aromatic aldehydes and methyl aryl ketones at ambient temperature to afford dihomoallylic secondary amines in moderate to high yields.

  在环境温度下，烯丙基溴化溴会添加到衍生自芳族醛和甲基芳基酮的肟中，从而以中等至高收率的价格提供二烯丙基芳族仲胺。
• A regioselective synthesis of 1-haloisoquinolines via ruthenium-catalyzed cyclization of O-methylbenzohydroximoyl halides with alkynes
  作者：Ravi Kiran Chinnagolla、Sandeep Pimparkar、Masilamani Jeganmohan

  DOI：10.1039/c3cc41269e

  日期：——

  A ruthenium-catalyzed highly regioselective cyclization of substituted N-methoxy benzimidoyl halides with alkynes in the presence of CsOAc (25 mol%) to give substituted 1-halo and 1-alkoxy substituted isoquinolines in good to excellent yields is described.

  描述了在 CsOAc（25 mol%）存在下，钌催化取代的 N-甲氧基苯亚甲酰卤与炔烃的高区域选择性环化反应，从而以良好到极佳的收率得到取代的 1-卤代和 1-烷氧基取代的异喹啉。
• Novel One-Pot Synthesis of <i>N</i>-Alkyl Arylamines from Oxime Ethers Using Organometallic Reagents
  作者：Takeaki Naito、Partha Mukhopadhyay、Okiko Miyata

  DOI：10.1055/s-2007-980358

  日期：2007.6

  α-disubstituted secondary arylamines from oxime ethers has been developed by two separate additions of organometallic reagents. As a related arylamine construction, very efficient synthesis of N-(diallyl)methyl arylamines is achieved via domino reactions involving addition-eliminative re-arrangement-addition reactions of acyclic and cyclic oxime ethers with allylmagnesium bromide.

  通过两次单独添加有机金属试剂，开发了一种从肟醚中合成 α,α-二取代仲芳胺的新型一锅法。作为相关的芳胺结构，N-(二烯丙基)甲基芳胺的非常有效的合成是通过多米诺反应实现的，该反应涉及无环和环状肟醚与烯丙基溴化镁的加成-消除重排-加成反应。

表征谱图