7-甲氧基-2H-苯并吡喃-3-甲醛 | 57543-39-2

• 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: 7-甲氧基-2H-苯并吡喃-3-甲醛
• 英文名称: 7-methoxy-2H-chromene-3-carbaldehyde
• 英文别名: 7-methoxy-2H-chromene-3-carbaldehyde；7-methoxy-2H-1-benzopyran-3-carboxyaldehyde；3-Formyl-7-methoxy-Δ³-chromen
• CAS: 57543-39-2
• 化学式: C₁₁H₁₀O₃
• mdl: MFCD01662419
• 分子量: 190.199
• InChiKey: ODUYMNRQOUHOBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  7-甲氧基-2H-苯并吡喃-3-甲醛 生成 3-[(N-aminocarbonyl-N-hydroxy)aminomethyl]-7-methoxy-3,4-dihydro-2H-1-benzopyran
  参考文献：
  名称：

  Certain benzopyran and benzothiopyran derivatives

  摘要：

  该发明涉及以下式的化合物##STR1##其中每个R独立地代表氢、较低的烷基、卤素、三氟甲基、较低的烷氧基、碳环或杂环芳基、碳环或杂环芳氧基、碳环或杂环芳基-较低烷氧基、碳环或杂环芳基-较低烷基、C.sub.3-C.sub.7-环烷基-较低烷氧基、或C.sub.3-C.sub.7-环烷氧基；R.sub.1代表氢、较低烷基或碳环芳基；R.sub.2代表氢或较低烷基；Y代表氧（O）、硫（S）、亚砜或磺酰基；n代表1、2或3；A代表直链键或较低烷基；Z代表##STR2##其中R.sub.3代表氢或酰基；R.sub.4代表较低烷基、C.sub.3-C.sub.7-环烷基、碳环或杂环芳基、碳环或杂环芳基-较低烷基、或C.sub.3-C.sub.7-环烷基-较低烷基；或Z代表##STR3##其中X代表氧或硫，R.sub.3代表氢、酰基、较低烷氧羰基、氨基羰基、单-或双-较低烷基氨基羰基、较低烯基氨基羰基、较低炔基氨基羰基、碳环或杂环芳基-较低烷基氨基羰基、碳环或杂环芳胺基羰基；C.sub.3-C.sub.7-环烷基氨基羰基，或C.sub.3-C.sub.7-环烷基-较低烷基氨基羰基；R.sub.5代表较低烷基、较低烷氧羰基-较低烷基、C.sub.3-C.sub.7-环烷基、碳环或杂环芳基、碳环或杂环芳基-较低烷基、C.sub.3-C.sub.7-环烷基-较低烷基、氨基、单-或双-较低烷基氨基、较低烯基氨基、较低炔基氨基、碳环或杂环芳基-较低烷基氨基、碳环或杂环芳胺基、C.sub.3-C.sub.7-环烷基氨基、C.sub.3-C.sub.7-环烷基-较低烷基氨基、较低烷氧羰基-较低烷基氨基，或较低烷氧基；R.sub.6和R.sub.7独立地代表氢或较低烷基；及其药学上可接受的盐；这些化合物可用作5-脂氧酶抑制剂。

  公开号：

  US05155130A1
• 作为产物：
  描述：

  7-甲氧基-2H-色烯-3-甲腈 在 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以93.5%的产率得到7-甲氧基-2H-苯并吡喃-3-甲醛
  参考文献：
  名称：

  Synthesis and biological evaluations of chalcones, flavones and chromenes as farnesoid x receptor (FXR) antagonists

  摘要：

  Farnesoid X receptor (FXR), a nuclear receptor mainly distributed in liver and intestine, has been regarded as a potential target for the treatment of various metabolic diseases, cancer and infectious diseases related to liver. Starting from two previously identified chalcone-based FXR antagonists, we tried to increase the activity through the design and synthesis of a library containing chalcones, flavones and chromenes, based on substitution manipulation and conformation (ring closure) restriction strategy. Many chalcones and four chromenes were identified as microM potent FXR antagonists, among which chromene 11c significantly decreased the plasma and hepatic triglyceride level in KKay mice. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.02.037

文献信息

• Design, one-pot synthesis, molecular docking study, and antibacterial evaluation of novel 2H-chromene based imidazo[1,2-a]pyridine derivatives as potent peptide deformylase inhibitors
  作者：Nilima Priyadarsini Mishra、Seetaram Mohapatra、Chita Ranjan Sahoo、Bishnu Prasad Raiguru、Sabita Nayak、Subhrakant Jena、Rabindra Nath Padhy

  DOI：10.1016/j.molstruc.2021.131183

  日期：2021.12

  one-pot three-component synthesis of a series of 2H-chromene-based imidazo[1,2-a]pyridines had been designed and were synthesized. This protocol was developed by the reaction of substituted 2H-chromene aldehydes and 2-aminopyridine in a mixture of nitroalkane and DMF under microwave irradiation at 60W, 100°C in 15 min with the presence of FeCl3 as the catalyst. The products were obtained in excellent

  设计并合成了一系列2 H-色烯基咪唑并[1,2-a]吡啶的高效、环保、一锅三组分合成方法。该方案是通过取代的 2 H-色烯醛和 2-氨基吡啶在硝基烷烃和 DMF 的混合物中在 60W、100°C 的微波辐射下反应 15 分钟，并存在 FeCl 3作为催化剂而开发的。以优异的收率获得了具有高官能团耐受性的产物。所有这些化合物都在体外进行了进一步研究用于通过琼脂井扩散法评估对人类致病性革兰氏阳性菌和革兰氏阴性菌的抗菌效力，并确定最小抑菌浓度 (MIC) 值。实际上，化合物13i在计算机模拟中强烈抑制革兰氏阴性大肠杆菌中的肽去甲酰酶 (MIC = 16 μg/ml) 。从基于生物和分子对接结果的构效关系和强效抗菌活性来看，可以说所选的合成化合物可用作强效的可药用抗菌剂。
• Copper-Catalyzed Enantioselective Henry Reaction of Enals and Subsequent Iodocyclization: Stereoselective Construction of Chiral Azatricyclic Frameworks
  作者：Yirong Zhou、Yuequan Zhu、Shaobai Yan、Yuefa Gong

  DOI：10.1002/anie.201305148

  日期：2013.9.23

  In the frame: A cascade sequence combining an asymmetric Henry reaction and a stereoselective intramolecular iodocyclization provides direct access to an enantioenriched tricyclic hexahydrochromeno[4,3‐b]pyrrole framework (see scheme). The Henry reaction is catalyzed by copper in the presence of L1.

  在框架中：级联序列结合了不对称的亨利反应和立体选择性的分子内碘环化作用，可直接进入对映体富集的三环六氢色素[4,3- b ]吡咯骨架（参见方案）。在L1存在下铜催化了亨利反应。
• ¹ H and ¹³ C NMR spectral assignments of novel chromenylchalcones
  作者：Hyuk Yoon、Seunghyun Ahn、Doseok Hwang、Geunhyeong Jo、Dong Woon Kim、Sang Ho Kim、Dongsoo Koh、Yoongho Lim

  DOI：10.1002/mrc.3873

  日期：2012.11

  were also synthesized through the same reaction between aldehydes (I) and ketone (II). Their complete 1H‐NMR and 13C‐NMR assignments are reported here and more polysubstituted chromenylchalcones synthesized or isolated from the natural sources in the future can be identified on the basis of the NMR data reported here. Copyright © 2012 John Wiley & Sons, Ltd.

  合成了几种含有 2H-色烯基团的查耳酮。2H-chromen-3-甲醛 (I) 与甲氧基取代的苯乙酮的 Claisen-Schmidt 缩合得到 (E)-3-(2H-chromen-3-yl)-1-(甲氧基苯基)prop-2-en-1-ones （色基查耳酮，1-7）。其他类型的色烯基查尔酮 (E)-1-(6-甲氧基-2H-色烯-3-基)-3-(甲氧基苯基)丙-2-烯-1-酮 (8-13)甲氧基取代的苯甲醛和 1-(6-甲氧基-2H-色烯-3-基)乙酮 (II)。Dichromenychalcones (14-16) 也通过醛 (I) 和酮 (II) 之间的相同反应合成。此处报告了它们完整的 1H-NMR 和 13C-NMR 归属，未来可以根据此处报告的 NMR 数据确定更多合成或从天然来源中分离的多取代的色基查耳酮。
• 신규한 칼콘 유도체 및 그 유도체를 포함하는 항암 조성물
  申请人：Konkuk University Industrial Cooperation Corp 건국대학교 산학협력단(220040157648) BRN ▼206-82-07325

  公开号：KR101566497B1

  公开（公告）日：2015-11-05

  본 발명은 신규한 칼콘 유도체 및 그 유도체를 포함하는 항암 조성물에 관한 것이다.

  这项发明涉及新型卡尔孔衍生物及包含该衍生物的抗癌组合物。
• A concise synthetic approach to brazilin via Pd-catalyzed allylic arylation
  作者：Youngeun Jung、Ikyon Kim

  DOI：10.1039/c5ob00216h

  日期：——

  A short synthetic route to the trimethyl ether of brazilin was developed in 6 steps from 7-methoxychromene with 78% overall yield. Regioselective installation of a formyl group onto 7-methoxychromene followed by reduction and acetylation afforded allylic acetate. Palladium-catalyzed allylic coupling of allylic acetate with arylboronic acid provided direct access to 3-benzylchromene which was converted

  从7-甲氧基苯并亚胺经6步开发了一条短的合成巴西三甲醚的合成路线，总收率为78％。将甲酰基区域选择性地安装在7-甲氧基亚甲基上，然后还原和乙酰化，得到乙酸烯丙酯。钯催化的烯丙基乙酸酯与芳基硼酸的烯丙基偶联提供了直接进入3-苄基亚甲基的途径，随后以高度简洁的方式进行二羟基化和酸催化的环化反应后，该3-苄基亚甲基被转化为目标分子。