2-methoxymethoxy-N,N-diethylbenzamide | 565176-53-6

• 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: 2-methoxymethoxy-N,N-diethylbenzamide
• 英文别名: N,N-diethyl-2-(methoxymethoxy)benzamide
• CAS: 565176-53-6
• 化学式: C₁₃H₁₉NO₃
• 分子量: 237.299
• InChiKey: YMJVCUULIFIXER-UHFFFAOYSA-N

物化性质

• 沸点：
  379.0±27.0 °C(Predicted)
• 密度：
  1.056±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.15
• 重原子数：
  17.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  38.77
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-methoxymethoxy-N,N-diethylbenzamide 在 盐酸 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 四甲基乙二胺 、 仲丁基锂 、 potassium carbonate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 、 异丙醇 、 乙腈 为溶剂， 反应 50.5h， 生成 5-chloro-8-methoxy-9-oxo-9H-fluoren-1-yl diethylcarbamate
  参考文献：
  名称：

  化学选择性钌催化 C-O 键活化：用于合成聚芳基芴酮的镍和钯催化反应的正交性

  摘要：

  报道了钌催化的甲氧基和 O-氨基甲酰基取代的芴酮的 C-O 键活化/芳基化。建立了化合物 1 (X = H) 到芳基 (2) 和 1,8-二芳基 (3) 芴酮的新反应。还描述了通过 Suzuki-Miyaura 反应得到 1,4-二芳基 (4) 和 1,4,8-三芳基芴酮 (5) 的正交钌、钯和镍催化反应。通过定向邻位和远程金属化策略可以随时获得起始甲氧基芴酮，这为所提出的反应提供了便利，这些反应可能会在材料科学领域得到应用。已经进行了 DFT 计算以合理化在钌催化反应中缺乏 C-H 键反应性。

  DOI：

  10.1055/s-0036-1590985
• 作为产物：
  描述：

  1-(甲氧基甲氧基)苯 、 N,N-二乙基氯甲酰胺 在 正丁基锂 、 四甲基乙二胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.5h， 以91%的产率得到2-methoxymethoxy-N,N-diethylbenzamide
  参考文献：
  名称：

  Studies towards the total synthesis of mumbaistatin: synthesis of highly substituted benzophenone and anthraquinone building blocks

  摘要：

  Model compounds and building blocks for a planned total synthesis of the highly potent glucose-6-phosphate (G6P) translocase inhibitor mumbaistatin (1) and structural analogs were elaborated: compound 1 represents a lead structure in the development of potential new antidiabetic drugs. With the model substrate 20 it was demonstrated that highly functionalized, tetra-ortho-substituted benzophenones can be prepared by nucleophilic addition of an aryllithium-building block to a benzaldehyde followed by oxidation. For compound 37, a potential precursor of the anthraquinone part of mumbaistatin, various approaches via aryne/phthalide annulations were developed and evaluated. The required functionalized arenes were prepared exploiting, among others, regioselective bromination and ortho-lithiation reactions. Coupling reactions of the anthracene-carbaldehyde 44 derived from 37 with various metalated arenes proved to be unexpectedly difficult and failed so far. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00427-7

文献信息

• Asymmetric synthesis of isobenzofuranone derivatives and their unique character as protein kinase Cα (PKCα) activators
  作者：Go Hirai、Yosuke Ogoshi、Megumi Ohkubo、Yuki Tamura、Toru Watanabe、Tadashi Shimizu、Mikiko Sodeoka

  DOI：10.1016/j.tetlet.2009.03.069

  日期：2009.7

  Efficient enantio-selective synthesis of conformationally constrained diacylglycerol analogues, 7-substituted isobenzofuranone derivatives, originally developed by us as PKC alpha ligands, was achieved by asymmetric dihydroxylation and gamma-lactone formation via ortho-lithiation and carboxylation. A series of derivatives having straight and/or branched side chains were synthesized and evaluated, and low-nanomolar-concentration affinity ligands and highly potent PKC alpha activators were found among them. These potent ligands induced phenotypic change of K562 cells, which is characteristic of PKC activators. (C) 2009 Elsevier Ltd. All rights reserved.
• Studies towards the total synthesis of mumbaistatin: synthesis of highly substituted benzophenone and anthraquinone building blocks
  作者：Florian Kaiser、Lothar Schwink、Janna Velder、Hans-Günther Schmalz

  DOI：10.1016/s0040-4020(03)00427-7

  日期：2003.4

  Model compounds and building blocks for a planned total synthesis of the highly potent glucose-6-phosphate (G6P) translocase inhibitor mumbaistatin (1) and structural analogs were elaborated: compound 1 represents a lead structure in the development of potential new antidiabetic drugs. With the model substrate 20 it was demonstrated that highly functionalized, tetra-ortho-substituted benzophenones can be prepared by nucleophilic addition of an aryllithium-building block to a benzaldehyde followed by oxidation. For compound 37, a potential precursor of the anthraquinone part of mumbaistatin, various approaches via aryne/phthalide annulations were developed and evaluated. The required functionalized arenes were prepared exploiting, among others, regioselective bromination and ortho-lithiation reactions. Coupling reactions of the anthracene-carbaldehyde 44 derived from 37 with various metalated arenes proved to be unexpectedly difficult and failed so far. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Chemoselective Ruthenium-Catalyzed C–O Bond Activation: Orthogonality of Nickel- and Palladium-Catalyzed Reactions for the Synthesis of Polyaryl Fluorenones
  作者：Victor Snieckus、Livia da Frota、Cédric Schneider、Mauro de Amorim、Alcides da Silva

  DOI：10.1055/s-0036-1590985

  日期：2017.12

  Ruthenium-catalyzed C–O bond activation/arylation of methoxy and O-carbamoyl-substituted fluorenones is reported. Established are new reactions of compound 1 (X = H) to aryl (2) and 1,8-diaryl (3) fluorenones. Orthogonal ruthenium-, palladium- and nickel-catalyzed reactions with Suzuki–Miyaura reactions to afford 1,4-diaryl (4) and 1,4,8-triaryl fluorenones (5) are also described. The ready availability

  报道了钌催化的甲氧基和 O-氨基甲酰基取代的芴酮的 C-O 键活化/芳基化。建立了化合物 1 (X = H) 到芳基 (2) 和 1,8-二芳基 (3) 芴酮的新反应。还描述了通过 Suzuki-Miyaura 反应得到 1,4-二芳基 (4) 和 1,4,8-三芳基芴酮 (5) 的正交钌、钯和镍催化反应。通过定向邻位和远程金属化策略可以随时获得起始甲氧基芴酮，这为所提出的反应提供了便利，这些反应可能会在材料科学领域得到应用。已经进行了 DFT 计算以合理化在钌催化反应中缺乏 C-H 键反应性。