6-chloro-2-trifluoromethylchromone | 242460-35-1

• 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: 6-chloro-2-trifluoromethylchromone
• 英文别名: 6-chloro-2-(trifluoromethyl)-4H-chromen-4-one；4H-1-Benzopyran-4-one, 6-chloro-2-(trifluoromethyl)-；6-chloro-2-(trifluoromethyl)chromen-4-one
• CAS: 242460-35-1
• 化学式: C₁₀H₄ClF₃O₂
• 分子量: 248.589
• InChiKey: BLDVZOZULZEBME-UHFFFAOYSA-N

物化性质

• 沸点：
  248.4±40.0 °C(Predicted)
• 密度：
  1.552±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-chloro-2-trifluoromethylchromone 在 硫酸 、 硝酸 作用下， 反应 0.17h， 以25%的产率得到6-chloro-5-nitro-2-trifluoromethylchromone
  参考文献：
  名称：

  摘要：

  Morpholine adds smoothly at the double bond of substituted 5- and 8-nitro-2-trifluoromethylchromones to form the corresponding 2-morpholino-2-trifluoromethylchroman-4-ones. 6- Methoxy-5-nitro-2-trifluoromethylchromone adds also benzylamine, whereas 7-methoxy-8-nitro -2-trifluoromethylchromone undergoes ring opening under the action of benzylamine to give 3-benzylamino-4,4,4-trifluoro-1 -(2-hydroxy-4-methoxy-3-nitrophenyl)but-2-en-1 -one.

  DOI：

  10.1023/a:1011357106750
• 作为产物：
  描述：

  6-chloro-2-hydroxy-2-trifluoromethylchroman-4-one 在 盐酸 、 溶剂黄146 作用下， 反应 0.05h， 以97%的产率得到6-chloro-2-trifluoromethylchromone
  参考文献：
  名称：

  摘要：

  Morpholine adds smoothly at the double bond of substituted 5- and 8-nitro-2-trifluoromethylchromones to form the corresponding 2-morpholino-2-trifluoromethylchroman-4-ones. 6- Methoxy-5-nitro-2-trifluoromethylchromone adds also benzylamine, whereas 7-methoxy-8-nitro -2-trifluoromethylchromone undergoes ring opening under the action of benzylamine to give 3-benzylamino-4,4,4-trifluoro-1 -(2-hydroxy-4-methoxy-3-nitrophenyl)but-2-en-1 -one.

  DOI：

  10.1023/a:1011357106750

文献信息

• Synthesis of 2-(trifluoromethyl)-1,2-dihydro-4H-thieno[2,3-c]chromen-4-ones and 2-(trifluoromethyl)-4H-thieno[2,3-c]chromen-4-ones from 2-trifluoromethylchromones and ethyl mercaptoacetate
  作者：Vyacheslav Ya Sosnovskikh、Boris I Usachev、Dmitri V Sevenard、Gerd-Volker Röschenthaler

  DOI：10.1016/s0040-4020(03)00329-6

  日期：2003.4

  mercaptoacetate in the presence of triethylamine results in the formation of 1,2-dihydrothieno[2,3-c]chromen-4-ones and diethyl 3,4-dithiadipate in high yields. Oxidation of the first compounds with nitrogen dioxide gave 1,2-dihydrothieno[2,3-c]chromen-3,4-diones which were converted into thieno[2,3-c]chromen-4-ones.

  在三乙胺的存在下，2-三氟甲基色酮与巯基乙酸乙酯的氧化还原反应可高产率地形成1,2-二氢噻吩并[2,3 - c ]铬-4-酮和3,4-二硫代二乙酯二乙酯。用二氧化氮氧化第一化合物，得到1,2-二氢噻吩并[2,3- c ] chromen-3,4-二酮，将其转化为噻吩并[2,3 - c ] chromen-4-ones。
• Reaction of 2-trifluoromethylchromones with cyanoacetic and malonic esters. Synthesis of new benzo[c]coumarin derivatives
  作者：V. Ya. Sosnovskikh、A. V. Safrygin、V. A. Anufriev

  DOI：10.1007/s11172-013-0320-x

  日期：2013.10

  2-trifluoromethylchromones with ethyl cyanoacetate and diethyl malonate in ethanol in the presence of sodium ethoxide furnished a number of new benzo[c]coumarin derivatives, which were formed with involvement of two ester molecules.

  在乙醇钠存在下，2-三氟甲基色酮与氰基乙酸乙酯和丙二酸二乙酯在乙醇中的回流提供了许多新的苯并[c]香豆素衍生物，这些衍生物是在两个酯分子的参与下形成的。
• Reactions of 2-(trifluoromethyl)chromones with cyanoacetamides, ethyl cyanoacetate and diethyl malonate. Unexpected synthesis of benzo[c]coumarin derivatives
  作者：Vyacheslav Ya. Sosnovskikh、Alexander V. Safrygin、Viktor A. Anufriev、Oleg S. Eltsov、Viktor O. Iaroshenko

  DOI：10.1016/j.tetlet.2011.09.082

  日期：2011.11

  2-(trifluoromethyl)chromones react with cyanoacetamides in the presence of sodium ethoxide to produce 6-(2-hydroxyaryl)-4-(trifluoromethyl)-2-oxo-1,2-dihydropyridine-3-carbonitriles, their reactions with ethyl cyanoacetate and diethyl malonate under the same conditions took an entirely different course and gave novel functionalized derivatives of 6H-benzo[c]chromen-6-one.

  尽管2-（三氟甲基）色酮在乙醇钠存在下与氰基乙酰胺反应生成6-（2-羟基芳基）-4-（三氟甲基）-2-氧代-1,2-二氢吡啶-3-甲腈，但它们与乙基的反应在相同条件下，氰基乙酸酯和丙二酸二乙酯采用完全不同的过程，得到了6 H-苯并[ c ] chromen-6-one的新型官能化衍生物。
• Reactions of 2-polyfluoroalkylchromones with aliphatic diamines
  作者：V. Ya. Sosnovskikh、V. A. Kutsenko

  DOI：10.1007/bf02496279

  日期：1999.4

  Abstract2-Polyfluoroalkylchromones react with aliphatic 1,2-diamines to give 2,3-dihydro-1H-1,4-diazepines. A similar reaction with 1,3-diaminopropane yieldsN,N′-trimethylenebis(2-hydroxyacetophenomines) as a result of scission of the original chromones.

  摘要 2-多氟烷基色酮与脂肪族 1,2-二胺反应生​​成 2,3-二氢-1H-1,4-二氮杂。由于原始色酮的断裂，与 1,3-二氨基丙烷的类似反应产生 N,N'-三亚甲基双（2-羟基苯乙胺）。
• 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。