3-methoxyacetophenone O-methyloxime | 142065-68-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-methoxyacetophenone O-methyloxime
• 英文别名: m-methoxyacetophenone-O-methyloxime；2-(1-methoxyiminoethyl)-4-methoxybenzene；1-(3-methoxyphenyl)ethan-1-one O-methyl oxime；1-(3-Methoxy-phenyl)-ethanone O-methyl-oxime；N-methoxy-1-(3-methoxyphenyl)ethanimine
• CAS: 142065-68-7
• 化学式: C₁₀H₁₃NO₂
• 分子量: 179.219
• InChiKey: NNRMQNSLHHZJHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  30.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-methoxyacetophenone O-methyloxime 在 Oxone 、 palladium diacetate 、 三苯基膦 作用下， 以 1,1,2,2-四氯乙烷 为溶剂， 反应 24.0h， 以85%的产率得到
  参考文献：
  名称：

  Ligand-Promoted Pd-Catalyzed Oxime Ether Directed C–H Hydroxylation of Arenes

  摘要：

  An efficient Pd-catalyzed oxime ether directed ortho C-H hydroxylation of arenes under neutral conditions has been developed. The efficiency of this hydroxylation is significantly improved by a ligand. Oxone, an inexpensive, readily available, and safe reagent, was employed as terminal oxidant and oxygen source. The challenging electron-deficient substrates could also be monohydroxylated in high efficiency. Drug modification with this protocol was also successfully demonstrated.

  DOI：

  10.1021/acscatal.5b01700
• 作为产物：
  描述：

  甲氧基胺盐酸盐 、 3-甲氧基苯乙酮 生成 3-methoxyacetophenone O-methyloxime
  参考文献：
  名称：

  叔丁基过氧化氢作为氧化剂的Pd催化芳基酮O-甲基肟与醛的邻位C-H酰化/交叉偶联

  摘要：

  开发了一种钯催化的方案，该方案通过使用叔丁基氢过氧化物（TBHP）作为氧化剂，通过芳基酮肟和醛的交叉偶联来直接进行CH键的酰化反应。用肟作为CH活化的指导基团，与醛的偶联具有显着的区域选择性。酰化反应显示出优异的官能团耐受性，并且脂族和杂芳族醛都可以有效地与肟偶联。

  DOI：

  10.1021/ol101618u

文献信息

• Access to Branched Allylarenes via Rhodium(III)-Catalyzed C–H Allylation of (Hetero)arenes with 2-Methylidenetrimethylene Carbonate
  作者：Shang-Shi Zhang、Yi-Chuan Zheng、Zi-Wu Zhang、Shao-Yong Chen、Hui Xie、Bing Shu、Jia-Lin Song、Yan-Zhi Liu、Yao-Fu Zeng、Luyong Zhang

  DOI：10.1021/acs.orglett.1c01832

  日期：2021.8.6

  A rhodium(III)-catalyzed C–H allylation of (hetero)arenes by using 2-methylidenetrimethylene carbonate as an efficient allylic source has been developed for the first time. Five different directing groups including oxime, N-nitroso, purine, pyridine, and pyrimidine were compatible, delivering various branched allylarenes bearing an allylic hydroxyl group in moderate to excellent yields.

  首次开发了使用 2-亚甲基亚甲基碳酸酯作为有效烯丙基来源的铑（III）催化（杂）芳烃的 C-H 烯丙基化反应。五种不同的导向基团包括肟、N-亚硝基、嘌呤、吡啶和嘧啶是相容的，以中等至极好的产率提供带有烯丙基羟基的各种支链烯丙基芳烃。
• Catalyst-Controlled [3 + 2] and [4 + 2] Annulations of Oximes with Propargyl Alcohols: Divergent Access to Indenamines and Isoquinolines
  作者：Wanchun Gong、Zhi Zhou、Jingjing Shi、Bo Wu、Biyun Huang、Wei Yi

  DOI：10.1021/acs.orglett.7b03546

  日期：2018.1.5

  Rhodium(III)- and iridium(III)-catalyzed C–H activation of oximes and coupling with propargyl alcohols is discussed. Depending on the catalyst, the reaction pathway switched between [3 + 2] and [4 + 2] annulations, thus giving divergent access to indenamines and isoquinolines in a one-pot and atom-economical manner. The hydroxyl group in the tertiary propargyl alcohol substrate was found to be crucial

  讨论了铑（III）和铱（III）催化肟的C–H活化以及与炔丙醇的偶联。取决于催化剂，反应路径在[3 + 2]和[4 + 2]环空之间切换，因此以一锅法和原子经济的方式提供了对茚满胺和异喹啉的不同途径。发现叔炔丙醇底物中的羟基对于控制化学选择性至关重要。五元的rhodacycle和iridacycle中间体也已被鉴定为机理假说。
• Direct Oxygenation of C–H Bonds through Photoredox and Palladium Catalysis
  作者：Sk. Sheriff Shah、Maniklal Shee、Amit Kumar Singh、Amrita Paul、N. D. Pradeep Singh

  DOI：10.1021/acs.joc.9b03197

  日期：2020.3.6

  This report presents the oxygenation of C-H bonds via the merger of photocatalysis and Pd catalysis. Herein, we describe the utilization of a photocatalyst to oxidize an organopalladium(II) intermediate to high-valent PdIII or PdIV intermediates, which promotes the formation of C-O bonds. The demonstrated method works efficiently with various directing groups, such as oxime ether and benzothiazole

  该报告介绍了通过光催化和Pd催化相结合的CH键的氧合。在这里，我们描述了利用光催化剂将有机钯（II）中间体氧化为高价PdIII或PdIV中间体，从而促进CO键的形成。所证明的方法可以有效地与各种导向基团一起使用，例如肟醚和苯并噻唑。通过合成可用于有机发光二极管和药物的2-（苯并[d]噻唑-2-基）苯酚的几种金属配合物，表明了这种直接CO键形成方法的适用性。
• Nitrate promoted mild and versatile Pd-catalysed C(sp²)–H oxidation with carboxylic acids
  作者：Xue Xiong、Yang-Jie Mao、Hong-Yan Hao、Yu-Ting He、Zhen-Yuan Xu、Gen Luo、Shao-Jie Lou、Dan-Qian Xu

  DOI：10.1039/d0ob01124j

  日期：——

  C(sp2)–H bond oxidation of oximes or azobenzenes with diverse carboxylic acids has been developed. In contrast to the previous catalytic systems, this protocol features mild conditions (close to room temperature for most cases) and a broad substrate scope (up to 64 examples), thus constituting a versatile method to directly prepare diverse O-aryl esters. Moreover, the superiority of the nitrate additive

  已经开发了一种硝酸盐促进的 Pd 催化的肟或偶氮苯与多种羧酸的温和交叉脱氢 C(sp 2 )-H 键氧化。与以前的催化系统相比，该协议具有温和的条件（大多数情况下接近室温）和广泛的底物范围（多达 64 个示例），从而构成了直接制备多种O-芳基酯的通用方法。此外，实验和计算证据进一步确定了硝酸盐添加剂在这种温和转变中的优势。
• Iridium(III)-Catalyzed Directed <i>ortho</i> -C(sp² )-H Amidation of Arenes with Sulfonamides
  作者：Wei Zhang、Darun Yang、Wengui Wang、Shoufeng Wang、Huaiqing Zhao

  DOI：10.1002/ejoc.201800192

  日期：2018.5.15

  A mild and efficient Cp*IrIII‐catalyzed (Cp* = pentamethylcyclopentadienyl) ortho‐C(sp2)–H amidation of O‐methyl ketoximes with sulfonamides is developed and furnishes the corresponding products in good yields.

  开发了一种温和有效的Cp * Ir III催化（Cp * =五甲基环戊二烯基）的O-甲基酮肟与磺酰胺酰胺化邻-C（sp 2）-H酰胺，并提供了高收率的相应产品。