4-chloro-2,2-dimethyl-2H-chromene-3-carboxaldehyde | 874663-07-7

• 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: 4-chloro-2,2-dimethyl-2H-chromene-3-carboxaldehyde
• 英文别名: 4-chloro-2,2-dimethyl-benzopyran-3-carbaldehyde；4-chloro-2,2-dimethyl-2H-chromene-3-carbaldehyde；4-Chloro-2,2-dimethylchromene-3-carbaldehyde；4-chloro-2,2-dimethylchromene-3-carbaldehyde
• CAS: 874663-07-7
• 化学式: C₁₂H₁₁ClO₂
• 分子量: 222.671
• InChiKey: JJGSNAWMTNAEAY-UHFFFAOYSA-N

物化性质

• 沸点：
  329.6±42.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-chloro-2,2-dimethyl-2H-chromene-3-carboxaldehyde 在 iron(III) chloride 、 碘 、 sodium hydride 、 magnesium 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 9-methoxy-6,6-dimethyl-7-thiophen-2-yl-6H,7H-chromeno[4,3-b]chromene
  参考文献：
  名称：

  An efficient synthesis of 6H,7H-chromeno[4,3-b]chromenes and 6,7-dihydrothio chromeno[3,2-c]chromenes as 9-substituted xanthene like analogs

  摘要：

  An efficient synthetic route with good overall yields to access 7-aryl/heteroaryl/alkyl substituted 6H,7H-chromeno[4,3-b]chromene, and 6,7-dihydrothiochromeno[3,2-c]chromene scaffolds has been developed. The route to these xanthene-like analogs involves a three-step reaction sequence: (1) Michael addition of readily available phenol and thiophenol to 4-chloro-2,2-dimethyl-2H-chromene-3-carbaldehyde, (2) Grignard reaction of different aryl, heteroaryl and alkyl magnesium bromides on the resulting carbaldehydes followed by (3) FeCl3 catalyzed spontaneous intramolecular Friedel-Craft's reaction on the diarylmethyl carbinols. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.08.127
• 作为产物：
  描述：

  2,2-二甲基-苯并二氢吡喃-4-酮 、 N,N-二甲基甲酰胺 在 三氯氧磷 作用下， 生成 4-chloro-2,2-dimethyl-2H-chromene-3-carboxaldehyde
  参考文献：
  名称：

  Microwave assisted [RuCl₂(p-cymene)₂]₂ catalyzed regioselective endo-tandem cyclization involving imine and alkyne activation: an approach to benzo[4,5]imidazo[2,1-a]pyridine scaffold

  摘要：

  通过金属催化的内环化策略，利用微波辅助高效合成苯并咪唑融合杂环的方法已经开发出来。

  DOI：

  10.1039/c4ra02581d

文献信息

• Diversity oriented synthesis of chromene-xanthene hybrids as anti-breast cancer agents
  作者：M. Srinivas Lavanya Kumar、Jyotsana Singh、Sudipta Kumar Manna、Saroj Maji、Rituraj Konwar、Gautam Panda

  DOI：10.1016/j.bmcl.2017.12.065

  日期：2018.2

  A diverse library of chromene-xanthene hybrids were synthesized through intramolecular Friedel-Crafts reaction of the arenoxy carbinols. Examples include first incorporation of amino acid tyrosine into xanthene skeletons with polar functionalities. A careful structural evaluation revealed that tyrosine crafted chromene-xanthene hybrids exhibited good activities against breast cancer cell lines MCF-7

  通过苯甲氧基甲醇的分子内Friedel-Crafts反应合成了色烯-x吨杂种的多样化文库。实例包括首先将氨基酸酪氨酸掺入具有极性官能团的x吨骨架中。仔细的结构评估表明，酪氨酸精制的色烯-x吨杂种对乳腺癌细胞系MCF-7，MDA-MB-231表现出良好的活性。铅化合物16在G1期表现出明显的细胞周期停滞，并诱导MDA-MB-231细胞凋亡。
• Synthesis, X-ray Structure, and Pharmacological Activity of Some 6,6-Disubstituted Chromeno[4,3-b]- and Chromeno- [3,4-c]-quinolines
  作者：Mohamed I. Hegab、Abdel-Samee M. Abdel-Fattah、Nabil M. Yousef、Hany F. Nour、A. M. Mostafa、Mohey Ellithey

  DOI：10.1002/ardp.200700089

  日期：2007.8

  Some chromeno[4,3‐b]quinolines 4a–i were obtained from β‐chloro carboxyaldehydes 3a–c with different aniline derivatives namely, aniline, 4‐fluoroaniline, and 2‐aminophenol. Surprisingly, 3a–c reacted with 2‐aminothiophenol and afforded the chromeno[3,4‐c]quinoline derivatives 5a–c. Single‐crystal X‐ray diffraction studies of 4e and 5b provided good support for the established structure. Compounds

  一些色诺 [4,3 - b] 喹啉 4a - i 是从 β - 氯甲醛 3a - c 与不同的苯胺衍生物即苯胺、4 - 氟苯胺和 2 - 氨基苯酚获得的。令人惊讶的是，3a-c 与 2-氨基苯硫酚反应得到色基 [3,4-c] 喹啉衍生物 5a-c。4e 和 5b 的单晶 X 射线衍射研究为已建立的结构提供了良好的支持。与吲哚美辛相比，化合物 4b 和 5b 显示出显着的抗炎和致溃疡评分活性。
• Halogen-Exchange Fluorination of β-Chlorovinyl Aldehydes - Unexpected Cascade Transformations in the Fluorination of 4-Chloro-2<i>H</i> -chromene and 4-Chloro-2<i>H</i> -thiochromene-3-carbaldehydes
  作者：Muthuramalingam Somasundaram、Jai Anand Garg、Shivaji Naidu、Venkatachalam Ramkumar、Ramanathan Saiganesh、Senthamaraikannan Kabilan、Kalpattu Kuppuswamy Balasubramanian

  DOI：10.1002/ejoc.201901069

  日期：2019.9.30

  One of the most facile and robust ways of incorporating fluorine atoms in organic substrates is through the Halex fluorination. We have described here the Halex fluorination of β‐chlorovinyl aldehydes using KF/DMSO system under mild conditions. Further the transformation of the fluoro‐substituted intermediates to its dimeric compounds via a cascade sequence of six steps is discussed.

  将氟原子掺入有机基质中最简便，最可靠的方法之一是通过Halex氟化法。我们在这里描述了在温和条件下使用KF / DMSO系统对β-氯乙烯基醛进行的Halex氟化。进一步讨论了通过六个步骤的级联序列将氟取代的中间体转化为其二聚体化合物。
• 4-Chloro-2,2-disubstituted Chromen-3-carboxaldehyde: Synthesis of some Fused Polycyclic Heterocycles as Anti-inflammatory, Analgesic, Anticonvulsant, and Antiparkinsonian Agents
  作者：Mohamed I. Hegab、Mohamed M. Abdulla

  DOI：10.1002/ardp.200500124

  日期：2006.1

  Some new aldazino 4, pyrazolo 5, thieno 8, and thiooxopyrimidino chromenes 10 were prepared via reaction of the corresponding β‐chlorocarboxaldehyde 3 with hydrazine hydrate, mercaptoacetic acid, and thiourea, respectively. Wherever, 4‐chlorochromene derivatives 2 along with 4‐chlorochromen‐3‐carboxaldehyde derivatives 3 were prepared from the corresponding ketone 1 with Vilsmeier‐Haack reagent. Some

  通过相应的β-氯代甲醛3与水合肼、巯基乙酸和硫脲反应，分别制备了一些新的aldazino 4、pyrazolo 5、thieno 8和thiooxopyrimidino chromenes 10。无论在哪里，4-氯色烯衍生物2和4-氯色烯-3-甲醛衍生物3都是用Vilsmeier-Haack试剂从相应的酮1制备的。一些新产品显示出与吲哚美辛、双氯芬酸、卡马西平和苯托品相当的良好抗炎、镇痛、抗惊厥和抗帕金森病活性。