2-(difluoromethyl)-6-nitrochromone | 380593-37-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2-(difluoromethyl)-6-nitrochromone
• 英文别名: 2-(difluoromethyl)-6-nitro-4H-chromen-4-one；2-(difluoromethyl)-6-nitrochromen-4-one
• CAS: 380593-37-3
• 化学式: C₁₀H₅F₂NO₄
• mdl: MFCD02626220
• 分子量: 241.151
• InChiKey: LROIYUPBFQASGG-UHFFFAOYSA-N

物化性质

• 沸点：
  338.2±42.0 °C(Predicted)
• 密度：
  1.536±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  吡哆醛盐酸盐 、 2-(difluoromethyl)-6-nitrochromone 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 以65%的产率得到11a-(difluoromethyl)-4-hydroxy-3-methyl-8-nitro-11a,13-dihydro-6H-1-benzopyrano[3',2':6,7]oxepino[3,4-c]pyridin-6-one
  参考文献：
  名称：

  2-（三氟甲基）色酮与吡x醛的反应：1-苯并吡喃并氧庚并-和1-苯并吡喃并吡喃并吡啶的形成

  摘要：

  吡rid醛与2-（三氟甲基）色酮进行oxa-Michael引发的闭环反应，生成11a，13-dihydro-6 H -1-苯并吡喃并[3'，2'：6,7]氧庚啶[3,4- c ]吡啶6 -ones和6 H，11a H -1-benzopyrano [3'，2'：5,6] pyrano [2,3- c ] pyridin-6-ones。吡ido醛的醇羟基参与初始的oxa-Michael加成反应生成了前一种产物，而苯基羟基的羟基参与了后者生成的产物。

  DOI：

  10.1016/j.jfluchem.2012.06.001

文献信息

• A Simple One-Pot Synthesis of 2,6-Disubstituted 4-(Polyfluoroalkyl)pyridines and -pyrimidines by Reaction of 2-Polyfluoroalkylchromones with Aromatic Methyl Ketimines and Amidines
  作者：Vyacheslav Ya. Sosnovskikh、Boris I. Usachev、Aleksei Yu. Sizov、Mikhail A. Barabanov

  DOI：10.1055/s-2004-822321

  日期：——

  The reaction of 2-polyfluoroalkylchromones with ketimines, derived from aromatic methyl ketones and isopropyl­amine, gives 2,6-diaryl-4-polyfluoroalkylpyridines in moderate to low yields. Benzamidine and guanidine also react with 2-polyfluoroalkylchromones to afford the corresponding 2,6-disubstituted 4-polyfluoroalkylpyrimidines.

  2-聚氟烷基铬酮与源自芳香性甲基酮和异丙胺的酮亚胺反应，得到2,6-二芳基-4-聚氟烷基吡啶，产率为中等到偏低。苄氨基和鸟氨酸也与2-聚氟烷基铬酮发生反应，生成相应的2,6-二取代的4-聚氟烷基嘧啶。
• Reaction of Polyhaloalkyl-Substituted Chromones, Pyrones, and Furanones with Salicylaldehydes as a Direct Route to Fused 2<i>H</i>-Chromenes
  作者：Vyacheslav Ya. Sosnovskikh、Vladislav Yu. Korotaev、Dmitry L. Chizhov、Igor B. Kutyashev、Danil S. Yachevskii、Olga N. Kazheva、Oleg A. Dyachenko、Valery N. Charushin

  DOI：10.1021/jo060459x

  日期：2006.6.1

  Polyhaloalkyl-substituted chromones, γ-pyrones, and β-furanones react with salicylaldehydes in the presence of piperidine to give a wide variety of fused 2H-chromenes in good yields. This novel annulation reaction presumably proceeds by a tandem intermolecular oxa-Michael addition and subsequent intramolecular Mannich condensation.

  在哌啶的存在下，多卤代烷基取代的色酮，γ-吡喃酮和β-呋喃酮与水杨醛反应，以高收率得到各种稠合的2 H-色酮。这种新颖的环化反应大概是通过串联分子间的氧杂-迈克尔加成反应以及随后的分子内曼尼希缩合反应而进行的。
• Synthesis of 6H,7H-pyrido[2,1-a]isoquinolinium zwitterions from 6-nitro-2-polyfluoroalkylchromones and 1,3,3-trimethyl-3,4-dihydroisoquinolines
  作者：V. Ya. Sosnovskikh、B. I. Usachev、T. S. Vshivkova、Yu. V. Shklyaev

  DOI：10.1007/s11172-014-0600-0

  日期：2014.6

  1,3,3-Trimethyl-3,4-dihydroisoquinolines and their crown-containing derivatives react with 6-nitro-2-polyfluoroalkylchromones in THF at room temperature with the formation of zwitterionic axially chiral 6H,7H-pyrido[2,1-a]isoquinolinium derivatives, which were converted to 2,6-diaryl-4-polyfluoroalkylpyridines, including those with the benzocrown-ether fragment.

  1,3,3-三甲基-3,4-二氢异喹啉及其含冠衍生物在THF中于室温下与6-硝基-2-多氟烷基色酮反应，形成两性离子轴向手性6H,7H-吡啶并[2,1- a]异喹啉鎓衍生物，其被转化为2,6-二芳基-4-多氟烷基吡啶，包括带有苯并冠醚片段的那些。
• Reaction of 2-Polyfluoroalkylchromones with 1,3,3-Trimethyl-3,4-dihydroisoquinolines and Methylketimines as a Direct Route to Zwitterionic Axially Chiral 6,7-Dihydrobenzo[<i>a</i>]quinolizinium Derivatives and 2,6-Diaryl-4-polyfluoroalkylpyridines
  作者：Vyacheslav Ya. Sosnovskikh、Boris I. Usachev、Aleksei Yu. Sizov、Ivan I. Vorontsov、Yurii V. Shklyaev

  DOI：10.1021/ol0351448

  日期：2003.8.1

  2-Polyfluoroalkylchromones react with 1,3,3-trimethyl-3,4-dihydroisoquinolines to give zwitterionic axially chiral 6,7-dihydrobenzo[a]quinolizinium derivatives in high yields. In addition, performing this reaction with aromatic methylketimines is a simple and convenient synthesis of 2,6-diaryl-4-polyfluoroalkylpyridines.
• Reaction of 2-(trifluoromethyl)chromones with pyridoxal: Formation of 1-benzopyranooxepino- and 1-benzopyranopyranopyridines
  作者：Vyacheslav Ya Sosnovskikh、Vladislav Yu Korotaev、Alexey Yu Barkov、Anna A. Sokovnina、Mikhail I. Kodess

  DOI：10.1016/j.jfluchem.2012.06.001

  日期：2012.9

  Pyridoxal undergoes oxa-Michael initiated ring closure with 2-(trifluoromethyl)chromones giving 11a,13-dihydro-6H-1-benzopyrano[3′,2′:6,7]oxepino[3,4-c]pyridin-6-ones and 6H,11aH-1-benzopyrano[3′,2′:5,6]pyrano[2,3-c]pyridin-6-ones. Participation of alcoholic hydroxy group of pyridoxal in the initial oxa-Michael addition leads to the former product and that of the phenyl hydroxy group to the later one

  吡rid醛与2-（三氟甲基）色酮进行oxa-Michael引发的闭环反应，生成11a，13-dihydro-6 H -1-苯并吡喃并[3'，2'：6,7]氧庚啶[3,4- c ]吡啶6 -ones和6 H，11a H -1-benzopyrano [3'，2'：5,6] pyrano [2,3- c ] pyridin-6-ones。吡ido醛的醇羟基参与初始的oxa-Michael加成反应生成了前一种产物，而苯基羟基的羟基参与了后者生成的产物。