3-(1,3-dioxolan-2-yl)-4,6-dinitrobenzo[d]isoxazole | 369389-93-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并异恶唑
• 英文名称: 3-(1,3-dioxolan-2-yl)-4,6-dinitrobenzo[d]isoxazole
• 英文别名: 3-(1,3-dioxolan-2-yl)-4,6-dinitro-1,2-benzoxazole
• CAS: 369389-93-5
• 化学式: C₁₀H₇N₃O₇
• 分子量: 281.181
• InChiKey: ZTKXKBZULVYZNT-UHFFFAOYSA-N

物化性质

• 沸点：
  500.4±45.0 °C(Predicted)
• 密度：
  1.665±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  136
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-(1,3-dioxolan-2-yl)-4,6-dinitrobenzo[d]isoxazole 在 甲酸 、 盐酸羟胺 作用下， 反应 15.0h， 以72%的产率得到4,6-dinitrobenzo[d]isoxazole-3-carbonitrile
  参考文献：
  名称：

  An Efficient One-Step Method for the Conversion of β-(Dimethylamino)sty­renes into Arylacetonitriles

  摘要：

  介绍了一种简便高效的一步法，通过β-(二甲氨基)苯乙烯与盐酸羟胺在甲酸溶液中的反应来制备苯乙腈。

  DOI：

  10.1055/s-2005-918405
• 作为产物：
  描述：

  在 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以87%的产率得到3-(1,3-dioxolan-2-yl)-4,6-dinitrobenzo[d]isoxazole
  参考文献：
  名称：

  摘要：

  A new procedure was developed for the preparation of 4,6-dinitro-3-R-benzo[d]isoxazoles (R are derivatives of the aldehyde group) based on 2,4,6-trinitrophenylacetaldehyde. The resulting compounds are characterized by the regiospecific substitution of the nitro group at position 4 under the action of anionic nucleophiles RS-, RO-, F-, or N-3(-), Which allowed the development of a new method for the preparation of previously unknown 4-Nu-6-nitro-3-R-benzo[d]isoxazoles (Nu is the residue of a nucleophile). At the same time, oxidative nucleophilic substitution under the action of anions of some beta -dicarbonyl compounds leads to the replacement of the hydrogen atom at position 7 with the corresponding C-nucleophiles.

  DOI：

  10.1023/a:1011313324497

文献信息

• Synthesis of 3-cyano-4,6-dinitrobenzo[d]isoxazole and its reactions with anionic nucleophiles
  作者：A. M. Starosotnikov、A. V. Lobach、Yu. A. Khomutova、S. A. Shevelev

  DOI：10.1007/s11172-006-0289-9

  日期：2006.3

  The action of various anionic O-, N-, and S-nucleophiles on 3-cyano-4,6-dinitro-benzo[d]isoxazole mostly resulted in regiospecific nucleophilic substitution for the nitro group in position 4. With an excess of an nucleophilic reagent, the nitro group in position 6 was also replaced.

  各种阴离子 O-、N-和 S-亲核试剂对 3-cyano-4,6-dinitro-benzo[d]isoxazole 的作用主要导致位置 4 硝基的区域特异性亲核取代。亲核试剂，6 位的硝基也被取代。
• Synthesis and oxidative cyclization of 7-amino-3-R-4,6-dinitrobenzo[d]isoxazoles
  作者：M. A. Bastrakov、A. M. Starosotnikov、I. V. Glukhov、S. A. Shevelev

  DOI：10.1007/s11172-010-0027-1

  日期：2009.2

  A method was developed for the selective amination of 3-R-4,6-dinitrobenzo[d]isoxazoles at position 7 via the oxidative nucleophilic substitution of hydrogen. The resulting nitroamines were used to synthesize representatives of the previously unknown tricyclic heteroaromatic system, viz., isoxazolo[5,4-e]benzofuroxan.

  开发了一种通过氢的氧化亲核取代在 7 位选择性胺化 3-R-4,6-二硝基苯并[d]异恶唑的方法。所得硝基胺用于合成以前未知的三环杂芳族系统的代表，即异恶​​唑并[5,4-e]苯并呋喃。
• 3-R-4-Nitro-6,7-furoxanobenzo[d]isoxazoles – a new type of condensed nitroarenes capable of Diels–Alder reaction
  作者：Maxim A. Bastrakov、Alexey M. Starosotnikov、Vadim V. Kachala、Igor L. Dalinger、Svyatoslav A. Shevelev

  DOI：10.1007/s10593-015-1726-1

  日期：2015.5

  Pericyclic [4+2] cycloaddition (Diels-Alder reaction) of nitrofuroxanobenzo[d]isoxazoles, capable of acting both as dienophiles (at the C=CNO2 bond) or heterodienes (at the C=C-N(O)=O fragment) was used to synthesize a new type of condensed polycyclic systems. The obtained compounds combining in one molecule two pharmacophore moieties, furoxan (nitric oxide donor) and substituted isoxazole, may be considered as a potential basis for the design of compounds with dual biological activity.