methyl 2-[acetyloxymethyl(6-nitro-1,3-benzodioxol-5-yl)]acrylate | 591250-17-8

• 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: methyl 2-[acetyloxymethyl(6-nitro-1,3-benzodioxol-5-yl)]acrylate
• 英文别名: Methyl 2-[acetyloxy-(6-nitro-1,3-benzodioxol-5-yl)methyl]prop-2-enoate
• CAS: 591250-17-8
• 化学式: C₁₄H₁₃NO₈
• 分子量: 323.259
• InChiKey: RJKOCWXAIQJZGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  117
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 2-[acetyloxymethyl(6-nitro-1,3-benzodioxol-5-yl)]acrylate 在 五甲基环戊二烯基二羰基铁二聚物 一氧化碳 作用下， 以 1,4-二氧六环 为溶剂， 150.0 ℃ 、607.95 kPa 条件下， 反应 80.0h， 以65%的产率得到methyl [1,3]dioxolo[4,5-g]quinoline-7-carboxylate
  参考文献：
  名称：

  Synthesis of 3-Substituted Quinolines via Transition-Metal-Catalyzed Reductive Cyclization of o-Nitro Baylis−Hillman Acetates

  摘要：

  Reductive cyclization of o-nitro-substituted Baylis-Hillman acetates by carbon monoxide, catalyzed by [Cp*Fe(CO)(2)](2), gives moderate to good yields of 3-substituted quinolines.

  DOI：

  10.1021/jo034447c
• 作为产物：
  描述：

  6-硝基胡椒醛 在 吡啶 、 三乙烯二胺 作用下， 以 二氯甲烷 为溶剂， 反应 169.0h， 生成 methyl 2-[acetyloxymethyl(6-nitro-1,3-benzodioxol-5-yl)]acrylate
  参考文献：
  名称：

  Synthesis of 3-Substituted Quinolines via Transition-Metal-Catalyzed Reductive Cyclization of o-Nitro Baylis−Hillman Acetates

  摘要：

  Reductive cyclization of o-nitro-substituted Baylis-Hillman acetates by carbon monoxide, catalyzed by [Cp*Fe(CO)(2)](2), gives moderate to good yields of 3-substituted quinolines.

  DOI：

  10.1021/jo034447c

文献信息

• Antileishmanial assessment of isoxazole derivatives against <i>L. donovani</i>
  作者：Sushobhan Mukhopadhyay、Dinesh S. Barak、R. Karthik、Sarvesh K. Verma、Rabi S. Bhatta、Neena Goyal、Sanjay Batra

  DOI：10.1039/d0md00083c

  日期：——

  The antileishmanial activity of a variety of 3-nitro and 3-amino-isoxazoles against promastigote and amastigote stages of L. donovani is described.

  描述了多种3-硝基和3-氨基异噁唑对唐氏利什曼原虫旋毛虫和无毛虫阶段的抗利什曼活性。
• Straightforward Strategy for the Stereoselective Synthesis of Spiro-Fused (C-5)Isoxazolino- or (C-3)Pyrazolino-(C-3)quinolin-2-ones from Baylis-Hillman Adducts by 1,3-Dipolar Cycloaddition and Reductive Cyclization
  作者：Virender Singh、Vijay Singh、Sanjay Batra

  DOI：10.1002/ejoc.200800746

  日期：2008.11

  A straightforward and general approach for the stereoselective synthesis of spiro-fused (C-5)isoxazolino- or (C-3)pyrazolino-(C-3)quinolin-2-ones from the adducts offorded from the Baylis–Hillman reaction of 2-nitrobenzaldehyde and ethyl acrylate by sequential 1,3-dipolar cycloaddition and reductive cyclization is presented. It was found that the reductive cyclization of the isoxazoline derivatives

  从 2 的 Baylis-Hillman 反应提供的加合物立体选择性合成螺稠合 (C-5)isoxazolino- 或 (C-3)pyrazolino-(C-3)quinolin-2-ones 的直接和通用方法-硝基苯甲醛和丙烯酸乙酯通过顺序 1,3-偶极环加成和还原环化反应。发现异恶唑啉衍生物的还原环化在 In/HCl 存在下有效进行，而吡唑啉的类似还原在 Fe/AcOH 混合物存在下进行时产生更好的产率。然而，使用 2-硝基苯甲醛和甲基乙烯基酮的 Baylis-Hillman 加合物的类似尝试没有产生所需的化合物。（© Wiley-VCH Verlag GmbH & Co. KGaA，69451 Weinheim，德国，2008 年）
• Synthesis of Substituted 1H- and 3H-1-Benzazepines and Rearrangement of Alkyl 1H-1-Benzazepine-2-carboxylates into Isoquinolines
  作者：Vijay Singh、Sanjay Batra

  DOI：10.1002/ejoc.200700175

  日期：2007.6

  reduction of nitro groups in 2-nitro-4-(2-nitrobenzylidene)alkanoates and 4-nitro-2-(2-nitroalkylidene)alkanoates allows the facile synthesis of substituted 1H-1-benzazepines and 3H-1-benzazepines. This reaction proceeds via SN2′ reaction of ethyl nitroacetate and nitroethane with the acetyl derivatives of Baylis–Hillman adducts deriving from 2-nitro-substituted benzaldehydes. During the study, an unprecedented

  SnCl2 介导的 2-硝基-4-(2-硝基亚苄基)链烷酸酯和 4-硝基-2-(2-硝基亚烷基)链烷酸酯中硝基的还原允许轻松合成取代的 1H-1-苯并氮杂和 3H-1-苯并氮杂。该反应通过硝基乙酸乙酯和硝基乙烷与源自 2-硝基取代苯甲醛的 Baylis-Hillman 加合物的乙酰衍生物的 SN2' 反应进行。在研究过程中，观察到 1H-benzazepine-2-carboxylate 烷基酯前所未有的重排为取代的异喹啉。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
• Efficient Transformation of Alkyl 3-nitro-5-(aryl/alkyl)isoxazole-4-carboxylates into 3-amino- and 3-hydrazinyl-5-aryl/alkyl-isoxazole-4-carboxylates in Aqueous Solution
  作者：Sushobhan Mukhopadhyay、Dinesh S. Barak、Ilesha Avasthi、Sanjay Batra

  DOI：10.1002/adsc.201700881

  日期：2017.11.23

  An efficient protocol for transforming alkyl 3‐nitro‐5‐(aryl/alkyl)isoxazole‐4‐carboxylates into 3‐amino‐ and 3‐hydrazinyl‐5‐aryl/alkyl‐isoxazole‐4‐carboxylates is described. The reaction that is carried out in aqueous acetonitrile solution generally afford the products without any chromatographic purification. Investigations with the substrate scope reveal that this protocol is compatible only when

  描述了将烷基3-硝基-5-（芳基/烷基）异恶唑-4-羧酸酯转化为3-氨基和3-肼基-5-芳基/烷基异恶唑-4-羧酸酯的有效方案。在乙腈水溶液中进行的反应通常得到产物，无需任何色谱纯化。对底物范围的研究表明，该方案仅在异恶唑环的C-4位上存在酯基时才兼容。
• Synthesis of 3,4,5-Trisubstituted Isoxazoles from Morita-Baylis-Hillman Acetates by an NaNO₂/I₂-Mediated Domino Reaction
  作者：Shashikant U. Dighe、Sushobhan Mukhopadhyay、Shivalinga Kolle、Sanjeev Kanojiya、Sanjay Batra

  DOI：10.1002/anie.201504529

  日期：2015.9.7

  3‐nitro‐5‐(aryl/alkyl)isoxazole‐4‐carboxylates is described. In a cascade event, initial Michael addition of NaNO2 to the MBH acetate furnishes the allylnitro intermediate which undergoes I2‐catalyzed oxidative α‐CH nitration of the nitromethyl subunit followed by [3+2] cycloaddition to afford the title compounds. Structural elaborations of these highly substituted isoxazoles by SNAr reactions and

  本文描述了一种有效的NaNO 2 / I 2介导的Morita-Baylis-Hillman（MBH）乙酸盐单酯转化为3-硝基--5-（芳基/烷基）异恶唑-4-羧酸烷基酯的方法。在一个级联事件，初始迈克尔加成纳米2到MBH醋酸配料其经历我的allylnitro中间2催化的氧化α-C 的硝基甲基亚基h的硝化，接着[3 + 2]环加成，得到标题化合物。这些高度取代的异恶唑通过S N Ar反应和氢解进行结构精制可以得到有用的产品。