6-氟-8-硝基色酮-3-甲醛 | 351003-07-1

• 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: 6-氟-8-硝基色酮-3-甲醛
• 中文别名: 6-氟-8-硝基苯并吡喃酮-3-甲醛；6-氟-8-硝基查尔酮-3-羧醛
• 英文名称: 6-fluoro-8-nitrochromone-3-carboxaldehyde
• 英文别名: 6-fluoro-8-nitro-4-oxochromene-3-carbaldehyde
• CAS: 351003-07-1
• 化学式: C₁₀H₄FNO₅
• 分子量: 237.144
• InChiKey: MFTIKIFELZBYLH-UHFFFAOYSA-N

物化性质

• 熔点：
  110-114 °C(lit.)
• 沸点：
  407.2±45.0 °C(Predicted)
• 密度：
  1.721±0.06 g/cm3(Predicted)
• 稳定性/保质期：

  常温常压下稳定，避免与强氧化剂接触。

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  89.2
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 海关编码：
  2932999099
• 安全说明：
  S26,S36

反应信息

• 作为反应物：
  描述：

  6-氟-8-硝基色酮-3-甲醛 、 1-(3-氯苯基)-3-甲基-5-吡唑啉酮 反应 0.02h， 以89%的产率得到2-(3-chlorophenyl)-4-(6-fluoro-8-nitro-4-oxo-4H-chromen-3-ylmethylene)-5-methyl-2,4-dihydropyrazol-3-one
  参考文献：
  名称：

  Rational design, synthesis and evaluation of chromone-indole and chromone-pyrazole based conjugates: Identification of a lead for anti-inflammatory drug

  摘要：

  Conjugates of chromone-indole and chromone-pyrazole were screened for cyclooxygenase-2 (COX-2), cyclooxygenase-1 (COX-1) and 5-lipoxygenase (5-LOX) inhibitory activities. Compounds 8 and 9 were identified as preferred inhibitors of COX-2 over the other two enzymes. Their IC50 for COX-2 was 29 nM and 20 nM, respectively and selectivity indices (SI) for COX-2 over COX-1 was 46 and 337. NMR, mass spectral studies and molecular modelling also indicated preferential interactions of compounds 8 and 9 with COX-2. Tested on albino mice against capsaicin induced algesia, compound 8 exhibited analgesic potential comparable to diclofenac. In addition to the biological profile, the desirable physico-chemical properties of these compounds make them promising leads for anti-inflammatory drugs. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.03.003

文献信息

• Palladium-Catalyzed Decarboxylative Aza-Michael Addition−Allylation Reactions between Allyl Carbamates and Activated Olefins. Generation of Quaternary Carbon Adjacent to Secondary Amine Carbon Center
  作者：Nitin T. Patil、Zhibao Huo、Yoshinori Yamamoto

  DOI：10.1021/jo061110c

  日期：2006.9.1

  The reaction of allyl carbamates with activated olefins in the presence of Pd(PPh3)(4) catalyst in THF proceeded smoothly at room temperature to give the corresponding, beta,alpha-bisadducts, beta-amino-alpha-allylated products, in high yields. Not only highly activated olefins containing two cyano groups but also 2-cyano enones underwent facile aza-Michael addition-allylation with various allylic carbamates giving the corresponding products in high yields and with high diastereoselectivities. The stereochemistry of the singly formed product was confirmed with the help of X-ray crystallographic technique. It is an excellent method for creating beta-amino alpha-allyl ketones having two contiguous stereocenters: quaternary carbon adjacent to secondary amine carbon center.