5-[2-(4-chlorophenyl)-3-nitropropyl]-3-methyl-4-nitroisoxazole | 929719-05-1

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 5-[2-(4-chlorophenyl)-3-nitropropyl]-3-methyl-4-nitroisoxazole
• 英文别名: 5-[2-(4-Chlorophenyl)-3-nitropropyl]-3-methyl-4-nitro-1,2-oxazole
• CAS: 929719-05-1
• 化学式: C₁₃H₁₂ClN₃O₅
• 分子量: 325.708
• InChiKey: FTCMXWSIIBTREK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  118
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-[2-(4-chlorophenyl)-3-nitropropyl]-3-methyl-4-nitroisoxazole 在 盐酸 、 sodium hydroxide 、 一水合肼 、 tin(ll) chloride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 54.0h， 生成 6-(4-chlorophenyl)-3-methyl-1,4,6,7-tetrahydropyrazolo[4,3-b]pyridin-5-one
  参考文献：
  名称：

  Modular synthesis of isoxazolopyridones and pyrazolopyridones

  摘要：

  Herein we described the preparation of two novel heterocyclic nuclei isoxazolopyridone and pyrazolopyridone. The syntheses are modular in nature and fast to execute. The title compounds were obtained pure without intervention of chromatography. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.12.044
• 作为产物：
  描述：

  3,5-二甲基-4-硝基异噁唑 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 5-[2-(4-chlorophenyl)-3-nitropropyl]-3-methyl-4-nitroisoxazole
  参考文献：
  名称：

  Modular synthesis of isoxazolopyridones and pyrazolopyridones

  摘要：

  Herein we described the preparation of two novel heterocyclic nuclei isoxazolopyridone and pyrazolopyridone. The syntheses are modular in nature and fast to execute. The title compounds were obtained pure without intervention of chromatography. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.12.044

文献信息

• Catalytic Asymmetric Conjugate Addition of Nitroalkanes to 4-Nitro-5-styrylisoxazoles
  作者：Andrea Baschieri、Luca Bernardi、Alfredo Ricci、Surisetti Suresh、Mauro F. A. Adamo

  DOI：10.1002/anie.200905018

  日期：2009.11.23

  Nitro versus nitro: 4‐Nitro‐5‐styrylisoxazoles were used as masked α,β‐unsaturated carboxylic acids in the titled catalytic asymmetric transformation. The 4‐nitroisoxazole core acts as an activator of the conjugated alkene and a latent carboxylate functionality. The reaction proceeded with 5 mol % of a readily prepared phase‐transfer catalyst at room temperature with remarkable diastereo‐ and enantioselectivity

  硝基与硝基：在标题为催化不对称转化中，使用4‐Nitro‐5‐styrylisoxazoles作为掩蔽的α，β‐不饱和羧酸。4-硝基异恶唑核心充当共轭烯烃的活化剂和潜在的羧酸盐官能团。反应在室温下以5摩尔％的现成相转移催化剂进行，反应具有非对映选择性和对映选择性（参见方案）。
• Preparation of mono-labelled aliphatic polyacids via isoxazole derivatives
  作者：Mauro F.A. Adamo、Piero Sarti-Fantoni、Stefano Chimichi、Alessandro Sandrelli

  DOI：10.1016/j.tetlet.2010.09.113

  日期：2010.12

  A method allowing the selective oxygen labelling of aliphatic polyacids, for example, succinic and glutaric acids, is reported. This process is based on the hydrolysis of a 3-alkyl-4-nitroisoxazol-5-yl group by Na18OH and affords the products in high yields. The same procedure was applied for the preparation of labelled aliphatic carboxylic acids.

  报道了允许对脂肪族多元酸例如琥珀酸和戊二酸进行选择性氧标记的方法。该方法基于Na 18 OH水解3-烷基-4-硝基异恶唑-5-基团，并以高收率提供产物。相同的程序用于标记的脂肪族羧酸的制备。
• Practical route for N,O-heteroatom interchange in 3,5-disubstituted-4-nitroisoxazoles
  作者：Mauro F.A. Adamo、Donato Donati、Piero Sarti-Fantoni、Arianna Buccioni

  DOI：10.1016/j.tetlet.2007.12.019

  日期：2008.2

  Reaction of 3-methyl-4-nitro-5-alkylisoxazoles with hydroxylamine provides a practical means to interchange the N,O-heteroatoms on the isoxazole core thereby expanding the range of compounds obtainable from 3-methyl-4-nitro-5-styrylisoxazoles. (c) 2007 Elsevier Ltd. All rights reserved.
• Modular synthesis of isoxazolopyridones and pyrazolopyridones
  作者：Mauro F.A. Adamo、Eleanor F. Duffy、Donato Donati、Piero Sarti-Fantoni

  DOI：10.1016/j.tet.2006.12.044

  日期：2007.2

  Herein we described the preparation of two novel heterocyclic nuclei isoxazolopyridone and pyrazolopyridone. The syntheses are modular in nature and fast to execute. The title compounds were obtained pure without intervention of chromatography. (c) 2007 Elsevier Ltd. All rights reserved.