4-(4-chlorophenyl)-6,6-dimethyl-3-methylene-2-((trimethylsilyl)oxy)-1,2-oxazinane | 1168207-46-2

• 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-(4-chlorophenyl)-6,6-dimethyl-3-methylene-2-((trimethylsilyl)oxy)-1,2-oxazinane
• CAS: 1168207-46-2
• 化学式: C₁₆H₂₄ClNO₂Si
• 分子量: 325.911
• InChiKey: HVMZGJQTTXEKEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.12
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  21.7
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-(4-chlorophenyl)-6,6-dimethyl-3-methylene-2-((trimethylsilyl)oxy)-1,2-oxazinane 在 四丁基氟化铵 作用下， 以 二氯甲烷 为溶剂， 反应 1.83h， 以27%的产率得到4-(4-chlorophenyl)-6,6-dimethyl-dihydro-2H-pyran-3(4H)-one O-trimethylsilyl oxime
  参考文献：
  名称：

  Rearrangement of 3-alkylidene-2-siloxy-tetrahydro-1,2-oxazines (ASENA). A new approach toward the synthesis of 3-α-hydroxyalkyl-5,6-dihydro-4H-1,2-oxazines

  摘要：

  A new approach toward the synthesis of 3-alpha-hydroxyalkyl-5,6-dihydro-4H-1,2-oxazines 1 from available 5,6-dihydro-4H-1,2-oxazine N-oxides 2 has been described. The key step of the process-the rearrangement of 3-alkiliden-2-siloxy-tetrahydro-1,2-oxazines 3 (ASENA)-was thoroughly investigated. Optimal experimental conditions were developed. A possible pathway of the ASENA rearrangement was proposed. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.03.082
• 作为产物：
  描述：

  4-(4-chlorophenyl)-3,6,6-trimethyl-5,6-dihydro-4H-1,2-oxazine 2-oxide 、 三甲基溴硅烷 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 4-(4-chlorophenyl)-6,6-dimethyl-3-methylene-2-((trimethylsilyl)oxy)-1,2-oxazinane
  参考文献：
  名称：

  N，N-二氧化烯胺与羧酸和磺酸酐的反应 α-羟基肟衍生物合成的新方法

  摘要：

  研究了N，N-二氧化烯胺与羧酸酐和磺酸酐的反应。描述了一种通过N，N-二氧化烯胺与三氟乙酸酐反应合成α-羟基肟衍生物的新方法。 1,2-恶嗪-三氟乙酸酐-羟基肟-烯胺-重排

  DOI：

  10.1055/s-0029-1216907

文献信息

• In Situ Generated Magnesium Cyanide as an Efficient Reagent for Nucleophilic Cyanation of Nitrosoalkenes and Parent Nitronates
  作者：Pavel Yu. Ushakov、Andrey A. Tabolin、Sema L. Ioffe、Alexey Yu. Sukhorukov

  DOI：10.1002/ejoc.201801761

  日期：2019.3.7

  In situ generated magnesium cyanide is a convenient, readily available, non‐volatile and organic‐soluble reagent for hydrocyanation reactions. Efficient nucleophilic cyanation of π‐electrophiles such as nitronates, conjugated nitrosoalkenes, imines, α,β‐unsaturated ketones, methylenemalonates and azoalkenes was demonstrated.

  原位生成的氰化镁是用于氢氰化反应的便捷，易得，不挥发且有机可溶的试剂。证明了π-亲电子试剂（如硝酸盐，共轭亚硝基烯烃，亚胺，α，β-不饱和酮，亚甲基丙二酸酯和偶氮烯烃）的高效亲核氰化。
• A General Metal-Assisted Synthesis of α-Halo Oxime Ethers from Nitronates and Nitro Compounds
  作者：Alexey Yu. Sukhorukov、Maria A. Kapatsyna、Tammy Lim Ting Yi、Hyeong Ryool Park、Yana A. Naumovich、Petr A. Zhmurov、Yulia A. Khomutova、Sema L. Ioffe、Vladimir A. Tartakovsky

  DOI：10.1002/ejoc.201403083

  日期：2014.12

  α-halo oxime ethers from readily accessible nitronates and nitro compounds via bis(oxy)enamines is reported. A key step of the strategy involves the unprecedented reaction of bis(oxy)enamines with a metal (Co, Zn, Mg, Mn) halide that acts as both a promoter and halide (Br, I, Cl) source. A variety of cyclic and acyclic ethers of α-halo oximes, including previously unavailable trimethylsilyl ethers of α-iodo

  报道了一种通过双（氧）烯胺从容易获得的硝基化合物和硝基化合物合成 α-卤代肟醚的方法。该策略的一个关键步骤涉及双（氧）烯胺与金属（Co、Zn、Mg、Mn）卤化物的前所未有的反应，该卤化物既作为促进剂又作为卤化物（Br、I、Cl）源。各种 α-卤代肟的环状和非环状醚，包括以前无法获得的 α-碘肟的三甲基甲硅烷基醚，已经以良好到高的产率合成。
• Metal-assisted addition of a nitrate anion to bis(oxy)enamines. A general approach to the synthesis of α-nitroxy-oxime derivatives from nitronates
  作者：Yana A. Naumovich、Victoria Emily Buckland、Dmitry A. Sen'ko、Yulia V. Nelyubina、Yulia A. Khoroshutina、Alexey Yu. Sukhorukov、Sema L. Ioffe

  DOI：10.1039/c6ob00388e

  日期：——

  The synthesis of α-nitroxy-substituted oxime derivatives has been achieved by an unprecedented metal-assisted addition of a nitrate anion to bis(oxy)enamines, which are readily available from nitronates or nitroalkanes. The method has a broad scope and provides access to α-nitroxy-oximes and their cyclic ethers including nitroxy-substituted isoxazolines and dihydro-1,2-oxazines, which are of interest

  α-硝基氧基取代的肟衍生物的合成已通过前所未有的金属辅助将硝酸根阴离子添加到双（氧）烯胺中来实现，双（氧）烯胺很容易从硝酸盐或硝基烷烃中获得。该方法具有广泛的应用范围，可提供α-硝基氧肟及其环状醚，包括硝基氧基取代的异恶唑啉和二氢1,2-恶嗪，它们在生物活性分子的合成中作为潜在的NO供体和中间体而受到关注。 。