(Z)-1-(benzo[d][1,3]dioxol-5-yl)-N-methylmethanimine oxide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: (Z)-1-(benzo[d][1,3]dioxol-5-yl)-N-methylmethanimine oxide
• 英文别名: 1-(1,3-benzodioxol-5-yl)-N-methylmethanimine oxide
• 化学式: C₉H₉NO₃
• 分子量: 179.175
• InChiKey: QJLNAJPMGGSMKJ-YHYXMXQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  47.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-tosyloxy-3-pentanone 、 (Z)-1-(benzo[d][1,3]dioxol-5-yl)-N-methylmethanimine oxide 在 三乙胺 作用下， 以 2,2,2-三氟乙醇 为溶剂， 反应 2.0h， 以71%的产率得到(3R*,4R*,6R*)-3-(benzo[d][1,3]dioxol-5-yl)-2,4,6-trimethyl-1,2-oxazinan-5-one
  参考文献：
  名称：

  （3 + 3）含羰基的含氧烯丙基阳离子的环加成反应：对1,2-恶嗪酮的非对映选择性

  摘要：

  由容易获得的α-甲苯磺酰氧基原位制备羟基烯丙基阳离子，并在与硝酮的（3 + 3）环加成中充当瞬态亲电子伙伴。在温和的条件下，该方法为多取代的1,2-恶嗪酮提供了化学选择性和非对映选择性的途径。提出了逐步处理以合理化此变换的非对映选择性。

  DOI：

  10.1021/acs.orglett.8b00617
• 作为产物：
  描述：

  胡椒醛 、 N-甲基羟胺盐酸盐 在 sodium carbonate 作用下， 以 甲醇 为溶剂， 反应 16.25h， 以89%的产率得到(Z)-1-(benzo[d][1,3]dioxol-5-yl)-N-methylmethanimine oxide
  参考文献：
  名称：

  （3 + 3）含羰基的含氧烯丙基阳离子的环加成反应：对1,2-恶嗪酮的非对映选择性

  摘要：

  由容易获得的α-甲苯磺酰氧基原位制备羟基烯丙基阳离子，并在与硝酮的（3 + 3）环加成中充当瞬态亲电子伙伴。在温和的条件下，该方法为多取代的1,2-恶嗪酮提供了化学选择性和非对映选择性的途径。提出了逐步处理以合理化此变换的非对映选择性。

  DOI：

  10.1021/acs.orglett.8b00617

文献信息

• Efficient Synthesis of Isoxazolidine-Tethered Monolayer-Protected Gold Nanoparticles (MPGNs) via 1,3-Dipolar Cycloadditions under High-Pressure Conditions
  作者：Jun Zhu、Brandon M. Lines、Michael D. Ganton、Michael A. Kerr、Mark S. Workentin

  DOI：10.1021/jo702398r

  日期：2008.2.1

  3-dipolar cycloaddition. At atmospheric pressures, the reaction proceeds slowly (if at all) and makes this reaction impractical for the synthetic modification of the nanoparticles. However, by performing the reaction under the high-pressure conditions, the reaction proceeds efficiently and quantitatively. TEM shows that the use of high pressure does not affect the size of the gold nanoparticle core. The

  制备了包含约30％马来酰亚胺封端的十二烷硫醇盐/十二烷硫醇盐配体的马来酰亚胺改性的2.5±0.5nm混合单层保护的金纳米颗粒（2- C 12 MPGN）。的2 -C 12 MPGN用一系列硝酮（的反应一-我）在常压和高压（11 000个大气压）的条件下，形成相应的异恶唑烷改性的纳米粒子（3 -C 12MPGN）通过界面上的1,3-偶极环加成反应。在大气压下，反应进行得很慢（如果有的话），使该反应对于纳米粒子的合成改性不切实际。然而，通过在高压条件下进行反应，反应有效且定量地进行。TEM显示高压的使用不影响金纳米颗粒核的尺寸。通过1 H NMR光谱对3 -C 12 MPGN进行表征，方法是将与使用N-十二烷基马来酰亚胺（4）和相同的硝酮（a - i）形成5的模型反应得到的光谱进行比较。。另外，与具有所有硝酮的2- C 12 MPGN相比，用4进行环加成反应也更容易发生，这表明后者的环境会影响环加成反应。
• The Reaction of Nitrones with Cyclopropanes: A Convenient Preparation of Tetrahydro-1,2-oxazines
  作者：Michael Kerr、Cheryl Carson、Ian Young

  DOI：10.1055/s-2007-990864

  日期：2008.2

  undergo smooth reaction in the presence of ytterbium(III) triflate to form tetrahydro-1,2-oxazines with a high degree of regio- and stereocontrol. A three-component protocol has also been developed wherein the nitrone is generated in situ from an aldehyde and a hydroxylamine. The reactions are often high yielding with broad substrate scope. The multicomponent nature of the reaction makes it amenable

  Nitrones 和 dialkyl cyclopropane-1,1-dicarboxylates 在三氟甲磺酸镱 (III) 的存在下进行平稳反应，形成具有高度区域和立体控制的四氢 1,2-恶嗪。还开发了一种三组分方案，其中硝酮由醛和羟胺原位生成。该反应通常具有高产率和广泛的底物范围。该反应的多组分性质使其适用于化合物库的合成，并且还允许在面向目标的合成中开发高度收敛的策略。
• N-tert-Butyl and N-methyl nitrones derived from aromatic aldehydes inhibit macromolecular permeability increase induced by ischemia/reperfusion in hamsters
  作者：Ayres G. Dias、Carlos E.V. Santos、Fatima Z.G.A. Cyrino、Eliete Bouskela、Paulo R.R. Costa

  DOI：10.1016/j.bmc.2009.04.004

  日期：2009.6

  N-Alquil nitrones 1c and 3-6 were prepared from aromatic aldehydes and N-tert-butylhydroxylamine or N-methylhydroxylamine in good yields and soft conditions. Their protective effect against microvascular damages caused by ischemia/reperfusion in 'hamster cheek pouch' assay was investigated and compare with that observed for nitrones 1a,b and 2, previously studied. Nitrones 3b, 4b and 4c were the most active ones in inhibiting macromolecular permeability increase induced by ischemia/reperfusion when administered by gavage and intravenous, while 3a and 4a were active only after intravenous administration. N-tert-butylhydroxylamine and Nt-methylhydroxylamine, products of the hydrolysis of these nitrones, were weakly active when administered by gavage or intravenous. Nitrone (4a) was the most potent in inhibiting macromolecular permeability increase induced by histamine. In this case, N-tert-butylhydroxylamine was as active as 4a. The lypophylicity in nitrones, specially in N-methyl nitrones, play an important role on the protective action when compounds were administered by gavage. (C) 2009 Published by Elsevier Ltd.
• (3 + 3) Cycloaddition of Oxyallyl Cations with Nitrones: Diastereoselective Access to 1,2-Oxazinanes
  作者：Marie Cordier、Alexis Archambeau

  DOI：10.1021/acs.orglett.8b00617

  日期：2018.4.20

  Oxyallyl cations are prepared in situ from readily available α-tosyloxy ketones and act as transient electrophilic partners in (3 + 3) cycloaddition with nitrones. Under mild conditions, this method provides a chemoselective and diastereoselective route to polysubstituted 1,2-oxazinanes. A stepwise process is proposed to rationalize the diastereoselectivity of this transformation.

  由容易获得的α-甲苯磺酰氧基原位制备羟基烯丙基阳离子，并在与硝酮的（3 + 3）环加成中充当瞬态亲电子伙伴。在温和的条件下，该方法为多取代的1,2-恶嗪酮提供了化学选择性和非对映选择性的途径。提出了逐步处理以合理化此变换的非对映选择性。
• Photoredox-catalyzed cross-coupling of N-indolylacetic acids with nitrones: Access to indole-N-ethylamines
  作者：Na He、Yingying Yang、Zhi Qiao、Fan Zhu、Jun Lin、Xizhong Song、Yi Jin

  DOI：10.1016/j.tetlet.2023.154712

  日期：2023.9