4-chloro-6-methoxy-2H-chromene-3-carbaldehyde | 896633-52-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醛
• 英文名称: 4-chloro-6-methoxy-2H-chromene-3-carbaldehyde
• CAS: 896633-52-6
• 化学式: C₁₁H₉ClO₃
• 分子量: 224.644
• InChiKey: WLQJIABEURDEOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-chloro-6-methoxy-2H-chromene-3-carbaldehyde 在 potassium fluoride 、 二甲基亚砜 作用下， 反应 8.0h， 以75%的产率得到6,6′-dimethoxy-2,3-dihydro-3,3′-methylene bischromone
  参考文献：
  名称：

  β-氯丙二醛的卤素交换氟化-4-氯-2H-色烯和4-氯-2H-硫代色素-3-甲醛的氟化的级联转变

  摘要：

  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。

  DOI：

  10.1002/ejoc.201901069
• 作为产物：
  描述：

  4-甲氧基苯酚 在 草酰氯 、 三氟甲磺酸 、 potassium carbonate 、 三氟乙酸 作用下， 以 叔丁醇 为溶剂， 生成 4-chloro-6-methoxy-2H-chromene-3-carbaldehyde
  参考文献：
  名称：

  Synthesis, characterization, and antimicrobial activity of novel substituted 2H-chromenyl acrylates

  摘要：

  The present study deals with conventional Witting olefination of 2H-chromene-3-carbaldehydes with stabilized ylide in the presence of dichloromethane to afford (2E)-ethyl-3-(4-chloro-2H-chromen-3-yl) acrylate derivatives. All the products were found to have E-geometry at C=C bond. The synthesized compounds were characterized by spectral data such as IR, H-1 NMR and MS. Compounds were screened for antimicrobial activity against strains of gram positive, gram negative bacterial and fungal strains. All compounds showed good antibacterial and antifungal activity.

  DOI：

  10.1134/s1070363216120586

文献信息

• Metal‐Free Triplet Phosphors with High Emission Efficiency and High Tunability
  作者：Michael Koch、Karthikeyan Perumal、Olivier Blacque、Jai Anand Garg、Ramanathan Saiganesh、Senthamaraikannan Kabilan、Kallupattu Kuppusamy Balasubramanian、Koushik Venkatesan

  DOI：10.1002/anie.201402199

  日期：2014.6.16

  Design of highly efficient phosphorescent emitters based on metal‐ and heavy atom‐free boron compounds has been demonstrated by taking advantage of the singlet fission process. The combination of a suitable molecular scaffold and appropriate electronic nature of the substituents has been utilized to tailor the phosphorescence emission properties in solution, neat solid, and in doped PMMA thin films

  利用单线裂变过程，已经证明了基于无金属和重原子的硼化合物的高效磷光发射体的设计。合适的分子支架和合适的取代基的电子性质的组合已被用于调整溶液，纯固体和掺杂的PMMA薄膜中的磷光发射性能。
• Synthesis and in Silico Study of Novel Benzisoxazole‐Chromene Derivatives as Potent Inhibitors of Acetylcholinesterase: Metal‐Free Site‐Selective C−N Bond Formation <i>via</i> Aza‐Michael Reaction
  作者：Grace Victoria Govada、Sabbasani Rajasekhara Reddy

  DOI：10.1002/cbdv.202300573

  日期：2023.8

  An efficient metal-free approach for site selective C−N coupling reaction of benzo[d]isoxazole and 2H-chromene derivatives has been designed and developed against AchE. This nitrogen containing organo-base promoted methodology, which is both practical and environmentally friendly, provides an easy and suitable pathway for synthesizing Benzisoxazole-Chromene (BC) possessing poly heteroaryl moieties

  针对 AchE，设计并开发了一种有效的无金属方法，用于苯并[d]异恶唑和 2 H-色烯衍生物的位点选择性 CN 偶联反应。这种含氮有机碱促进的方法既实用又环保，为合成具有多杂芳基部分的苯并异恶唑-色烯（BC）提供了一种简单且合适的途径。将合成的 BC 衍生物4 a – n对接至 AChE 的活性位点，以获得对化合物结合模式的更多了解。其中，化合物4a和4l对 AChE 抑制表现出有效的活性和高选择性。最终对接结果表明，化合物4l与AChE的结合能最低，为-11.2260 kcal/mol。合成的BC类似物将成为促进药物化学研究中适当研究的潜在候选者。
• 10.1002/cbdv.202400719
  作者：Govada, Grace Victoria、Pal, Sanjivani、Panjacharam, Paranimuthu、Bhatt, Harshil Samir、Kumar, Sanjit、Lin, Chun-Cheng、Wang, Sheng-kai、Reddy, Sabbasani Rajasekhara

  DOI：10.1002/cbdv.202400719

  日期：——

  A versatile and efficient chemo selective synthesis of 4-aryl-3-formyl-2H-chromenes (AFC) was undertaken using Pd-catalyzed cross-coupling conditions. The key oxidative transmetalation was successfully applied to a significant range of substitutions on the chromene moiety and aryl ring in Ar(BOH)3, accommodating both electron-rich and electron-deficient groups. These π-extended scaffolds exhibited

  使用 Pd 催化交叉偶联条件进行了 4-芳基-3-甲酰基-2 H-色烯 (AFC) 的通用且高效的化学选择性合成。关键的氧化金属转移成功地应用于Ar(BOH) 3中色烯部分和芳环上的大量取代，同时容纳富电子和缺电子基团。这些π延伸支架表现出绿黄色荧光，具有大的斯托克斯位移和高量子产率。光物理性质的测量表明，色烯环中带有甲氧基取代的化合物3t引起显着的红移。通过该方法获得的AFC可以通过甲酰基色烯的功能化转化为具有生物活性的4-芳基-3-亚氨基安替比林-2H-色烯(AAC)。将具有甲氧基取代的 AFC 和 AAC（ 3t和4e ）对接以对抗 AChE 抑制，并且化合物4e具有最低的结合能 -11.20 kcal/mol。对代表性化合物进行的 DFT 计算表明，化合物4e比3t更具反应性，这与对接研究一致。
• Synthesis, characterization, and antimicrobial activity of novel substituted 2H-chromenyl acrylates
  作者：N. J. P. Subhashini、M. Ravi、D. Cherupally、B. China Raju、E. V. Reddy、H. Bee

  DOI：10.1134/s1070363216120586

  日期：2016.12

  The present study deals with conventional Witting olefination of 2H-chromene-3-carbaldehydes with stabilized ylide in the presence of dichloromethane to afford (2E)-ethyl-3-(4-chloro-2H-chromen-3-yl) acrylate derivatives. All the products were found to have E-geometry at C=C bond. The synthesized compounds were characterized by spectral data such as IR, H-1 NMR and MS. Compounds were screened for antimicrobial activity against strains of gram positive, gram negative bacterial and fungal strains. All compounds showed good antibacterial and antifungal activity.
• 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。