2,2-二甲基-3-硝基-2H-1-苯并吡喃 | 57544-29-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: 2,2-二甲基-3-硝基-2H-1-苯并吡喃
• 英文名称: 2,2-dimethyl-3-nitro-2H-chromene
• 英文别名: 2,2-dimethyl-3-nitrochromene；2,2-dimethyl-3-nitro-2H-chromene；2,2-Dimethyl-3-nitro-Δ³-chromen；2,2-Dimethyl-3-nitro-2H-chromen；2,2-Dimethyl-3-nitro-2H-1-benzopyran
• CAS: 57544-29-3
• 化学式: C₁₁H₁₁NO₃
• 分子量: 205.213
• InChiKey: DCZZXWWSCKHUHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,2-二甲基-3-硝基-2H-1-苯并吡喃 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 反应 3.0h， 以58%的产率得到4,4-dimethyl-1,4-dihydrochromeno[4,3-d][1,2,3]triazole
  参考文献：
  名称：

  Catalyst-free 1,3-dipolar cycloaddition of 3-nitrochromen with sodium azide: a facile method for the synthesis of 4-aryl-1,4-dihydrochromeno[4,3-d][1,2,3]triazole derivatives

  摘要：

  1,3-Dipolar cycloaddition of 3-nitrochromen with sodium azide under catalyst-free conditions afforded 4-aryl-1,4-dihydrochromeno[4,3-d][1,2,3]triazole derivatives at 80 degrees C in DMSO is described. The generality of this reaction was demonstrated by synthesizing an array of 4-aryl-1,4-dihydrochromeno[4,3d][1,2,3]triazole derivatives. Clean reaction conditions, easy isolation, and good yields of the triazoles are the salient features of the methodology. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.05.002
• 作为产物：
  描述：

  2,2,-二甲基-2H-苯并吡喃 在 aluminum oxide 、 氧化亚氮 作用下， 生成 2,2-二甲基-3-硝基-2H-1-苯并吡喃
  参考文献：
  名称：

  一氧化氮硝化烯烃制备硝基烯烃的简便方法

  摘要：

  在 1,2-二氯乙烷中用一氧化氮 (NO) 处理后，具有末端双键或与芳核共轭的烯烃成功硝化为硝基烯烃，产率从高到高。作为副产物形成的硝基醇通过随后用酸性活性氧化铝处理而脱水以产生硝基烯烃。通过GC分析，证实在本硝化过程中产生了等摩尔量的氮气。描述了一种可能的反应途径，包括形成硝基亚硝基化合物，即关键中间体。关键中间体通过与一氧化氮反应转化为硝基烯烃。

  DOI：

  10.1246/bcsj.68.3629

文献信息

• Assembly of fully substituted triazolochromenes via a novel multicomponent reaction or mechanochemical synthesis
  作者：Robby Vroemans、Yenthel Verhaegen、My Tran Thi Dieu、Wim Dehaen

  DOI：10.3762/bjoc.14.246

  日期：——

  triazolochromenes were formed with complete regioselectivity and new biologically relevant structures were synthesized via extension of the developed procedure and via postfunctionalization. The mechanochemical synthesis was carried out for several salicylaldehydes and gave a clear improvement in the yield of the corresponding triazolochromenes and consequently showed to be a viable alternative for solid salicylaldehydes

  一种新的无金属一锅三组分程序已被开发出来，该程序从市售材料开始，用于完全取代的三唑色烯。水杨醛和硝基烯烃在无溶剂条件下反应，然后以一锅两步顺序将中间体 3-硝基-2H-色烯与有机叠氮化物进行 1,3-偶极环加成。三唑色烯的形成具有完全的区域选择性，并且通过扩展已开发的程序和通过后功能化合成了新的生物学相关结构。对几种水杨醛进行了机械化学合成，并明显提高了相应三唑色烯的产率，因此表明它是固体水杨醛的可行替代品。
• “On-Water”-Promoted<i>C</i>-Alkylation of Indoles with 2-Aryl-3-nitro-2<i>H</i>-chromenes under Catalyst-Free Conditions
  作者：Pateliya Mujjamil Habib、Veerababurao Kavala、B. Rama Raju、Chun-Wei Kuo、Wen-Chang Huang、Ching-Fa Yao

  DOI：10.1002/ejoc.200900207

  日期：2009.9

  An environmentally benign method for the synthesis of indolyl(nitro)chromans from indoles and 2-aryl-3-nitro-2Hchromenes under catalyst-free conditions by use of an “onwater” concept is described. The salient features of the methodology are its clean reaction conditions, the eco-friendly

  描述了一种在无催化剂条件下通过使用“水上”概念从吲哚和 2-芳基-3-硝基-2Hchromenes 合成吲哚基（硝基）色满的环境友好方法。该方法的显着特点是其清洁的反应条件、环境友好的
• An easy and efficient method for the synthesis of 2,2-dialkyl-3-nitrochromene
  作者：Ming-Chung Yan、Yeong-Jiunn Jang、Ching-Fa Yao

  DOI：10.1016/s0040-4039(01)00284-2

  日期：2001.4

  Reactions of salicylaldehyde 1, 1,4-diazabicyclo[2.2.2]octane (DABCO), with beta -nitrostyrenes 2, 4, 12, 14. and 16, respectively, in the absence of solvent at 40 degreesC gave high yields of 3- nitro-chromenes. Only 96% of trans-3-nitro-4-hydroxyflavans 7 or 98% of 10 were isolated when compounds 6 or 9 reacted with 1 and DABCO under similar conditions. When the reaction temperature was increased to 90 degreesC, 7 and 10 underwent dehydration to generate 74% of 8 and 89% of 11. (C) 2001 Elsevier Science Ltd. All rights reserved.
• The Synthesis of 2,2-Disubstituted-3-nitrochromenes from Salicylaldehyde and 2,2-Disubstituted-1-nitroalkenes
  作者：Ching-Fa Yao、Ming-Chung Yan、Yeong-Jiunn Jang、Wen-Yu Kuo、Zhijay Tu、Kao-Hsien Shen、Ting-Shen Cuo、Chuen-Her Ueng

  DOI：10.3987/com-02-9454

  日期：——
• A Convenient Method for the Preparation of Nitro Olefins by Nitration of Olefins with Nitrogen Monoxide
  作者：Eiichiro Hata、Tohru Yamada、Teruaki Mukaiyama

  DOI：10.1246/bcsj.68.3629

  日期：1995.12

  Olefins with a terminal double bond or conjugated with aromatic nucleus are successfully nitrated into nitro olefins in good-to-high yields on treatment with nitrogen monoxide (NO) in 1,2-dichloroethane. Nitro alcohols formed as by-products are dehydrated to yield nitro olefins by the subsequent treatment with acidic activated alumina. By GC analysis, it was confirmed that an equimolar amount of nitrogen

  在 1,2-二氯乙烷中用一氧化氮 (NO) 处理后，具有末端双键或与芳核共轭的烯烃成功硝化为硝基烯烃，产率从高到高。作为副产物形成的硝基醇通过随后用酸性活性氧化铝处理而脱水以产生硝基烯烃。通过GC分析，证实在本硝化过程中产生了等摩尔量的氮气。描述了一种可能的反应途径，包括形成硝基亚硝基化合物，即关键中间体。关键中间体通过与一氧化氮反应转化为硝基烯烃。