1-oxo-1H-benzo[f]chromene-2-carbaldehyde | 23469-50-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 1-oxo-1H-benzo[f]chromene-2-carbaldehyde
• 英文别名: 1-Oxobenzo[f]chromene-2-carbaldehyde
• CAS: 23469-50-3
• 化学式: C₁₄H₈O₃
• 分子量: 224.216
• InChiKey: PSQJJMWXNFHILK-UHFFFAOYSA-N

物化性质

• 熔点：
  192-194 °C
• 沸点：
  409.5±45.0 °C(Predicted)
• 密度：
  1.439±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-oxo-1H-benzo[f]chromene-2-carbaldehyde 以67%的产率得到
  参考文献：
  名称：

  NOHARA A.; KURIKI H.; SAIJO T.; SUGIHARA H.; KANNO M.; SANNO Y., J. MED. CHEM. , 1977, 20, NO 1, 141-145

  摘要：

  DOI：
• 作为产物：
  描述：

  乙酸-2-萘酯 在 三氯化铝 、 三氯氧磷 作用下， 以 various solvent(s) 为溶剂， 生成 1-oxo-1H-benzo[f]chromene-2-carbaldehyde
  参考文献：
  名称：

  Formylchromone derivatives as a novel class of protein tyrosine phosphatase 1B inhibitors

  摘要：

  Formylchromone inhibits a human protein tyrosine phosphatase PTP1B with a IC50 value of 73 muM. The chemical reactivity of formylchromone was adjusted by substitution at various positions of the formylchromone skeleton. In an initial assessment of the structure-activity relationship, the most potent inhibitor showed an IC50 of 4.3 muM against PTP1B and strong or medium selectivity against other human PTPases, LAR and TC-PTP. This compound, however, was not selective against microbial PTPases. YPTP1 and YOP. The potency and selectivity of the formylchromone derivatives expecting further improvements provides a novel pharmacophore for the design of drugs for the treatmenrt of type 2 diabetes and obesity. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00479-7

文献信息

• Eco-friendly organocatalyst- and reagent-controlled selective construction of diverse and multifunctionalized 2-hydroxybenzophenone frameworks for potent UV-A/B filters by cascade benzannulation
  作者：Muhammad Saeed Akhtar、Raju S. Thombal、Ramuel John Inductivo Tamargo、Won-Guen Yang、Sung Hong Kim、Yong Rok Lee

  DOI：10.1039/d0gc01011a

  日期：——

  2-hydroxy-3′-formylbenzophenones and [4 + 2] cycloaddition for 2-hydroxybenzophenones. With this methodology, an unprecedented double benzannulation allows one-pot construction of diverse 7-(2′-hydroxybenzoyl)-2-naphthaldehydes via [3 + 3 + 4] cycloaddition. This protocol features a broad substrate scope, high functional-group tolerance, and operational simplicity in an environmentally benign green solvent

  在绿色下，由有机催化剂和试剂控制的高选择性合成各种功能化的新型2-羟基二苯甲酮骨架，例如2-羟基-3'-甲酰基二苯甲酮，7-（2'-羟基苯甲酰基）-2-萘醛和2-羟基二苯甲酮描述了开发有效的UV-A / B滤光片的条件。有机催化的苯环化反应分别通过[3 + 3]环加成反应进行2-羟基-3'-甲酰基二苯甲酮的合成，以及[4 + 2]环加成反应进行2-羟基二苯甲酮的合成。用这种方法，一个前所未有的双苯并环化允许一锅煮结构多样7-（2'-羟基苯甲酰基）-2-萘甲醛通过[3 + 3 + 4]环加成。该协议具有广泛的底物范围，高官能团耐受性和在环境友好的绿色溶剂中的操作简便性。合成的化合物已成功用于进一步转化，并已被很好地表征为有效的UV-A / B过滤剂。
• Construction of Halofunctionalized Indenes via a Cascade Prins‐Nazarov Cyclization Promoted by Dual Roles of BX ₃
  作者：Sabera Sultana、Yong Rok Lee

  DOI：10.1002/adsc.201901266

  日期：2020.2.21

  carboxaldehydes and boron trihalides (BX3, X=F, Cl, Br, I) is described. A diverse array of halofunctionalized indenes substituted with a heterocycle has been synthesized regioselectively with BX3 as a promotor for the carbocyclization and a source of X− for halogenation. This reaction proceeds via a formal halogenative [4+1] cycloaddition between arylalkynes and carboxaldehydes promoted by boron trihalides to generate

  描述了在特定类别的甲醛和三卤化硼（BX 3，X = F，Cl，Br，I）存在下，各种未活化的芳基炔烃向相应的1H-茚进行卤官能化的过程。用杂环取代的halofunctionalized茚的多样化已经BX区域选择性合成的3作为carbocyclization一个启动子和X的源-用于卤化。该反应通过由三卤化硼促进的芳基炔烃和甲醛之间的正式卤代[4 + 1]环加成反应进行，以生成卤代官能化的茚。卤代官能化的茚的有用性通过它们通过偶联，亲核取代和氧化转化为其他衍生物来证明。
• Direct construction of xanthene and benzophenone derivatives via Brønsted acid controlled Diels-Alder reaction of 3-vinylchromones and arynes
  作者：Xu-Jiao Huang、Yuan Tao、Yue-Kun Li、Xin-Yan Wu、Feng Sha

  DOI：10.1016/j.tet.2016.11.028

  日期：2016.12

  A Brønsted acid controlled Diels-Alder reaction of 3-vinylchromones with arynes has been developed. By employing different kinds and amounts of acid, 9-aryl-9H-xanthen-9-ols or ortho-hydroxybenzophenones could be controllably furnished in good yields in an atom- and step-economic manner.

  已经开发了3-乙烯基色酮与芳烃的布朗斯台德酸控制的Diels-Alder反应。通过使用不同种类和数量的酸，可以以原子经济和分步经济的方式可控制地以良好的产率提供9-芳基-9 H-黄嘌呤-9-ols或邻羟基二苯甲酮。
• A catalyst- and solvent-free thermal multicomponent approach for the construction of diverse and polysubstituted 2-aminopyridines and their antibacterial activity
  作者：Ek Raj Baral、Kavita Sharma、Muhammad Saeed Akhtar、Yong Rok Lee

  DOI：10.1039/c6ob02015a

  日期：——

  efficient and facile thermal multicomponent cascade reaction of readily available 4-oxo-4H-chromene-3-carbaldehydes with cyanoacetates or cyanoamides and anilines or aliphatic amines under solvent and catalyst-free conditions was developed for the synthesis of a range of polysubstituted 2-aminopyridine derivatives in good to excellent yield. This protocol proceeds via a cascade reaction of Knoevenagel condensation

  在无溶剂和无催化剂的条件下，开发了一种易于使用的4-氧代-4 H-苯甲基-3-甲醛与氰基乙酸酯或氰胺和苯胺或脂肪族胺的高效且便捷的热多组分级联反应，用于合成一系列多取代的2-氨基吡啶衍生物具有良好至优异的产率。该方案通过Knoevenagel缩合，亲核加成，分子内迈克尔加成和开环的级联反应进行。作为该方法的应用，评估了某些合成化合物的抗菌活性。
• Original Mitsunobu-Triggered Sequence Involved in a One-Pot Domino Process toward Tetracyclic Systems Bearing a Bis-<i>N</i>,<i>O</i>-acetal Junction
  作者：Thomas Lepitre、Clement Denhez、Morgane Sanselme、Mohamed Othman、Ata Martin Lawson、Adam Daïch

  DOI：10.1021/acs.joc.6b01523

  日期：2016.10.7

  Herein is reported an efficient, one-pot domino process through a 1,6-aza-Michael addition-triggered sequence and an original Mitsunobu-type concerted sequence for the synthesis of tetracyclic systems containing a bis-N,O-acetal junction. This methodology led to the construction of four new bonds, the cleavage of three C–O bonds, and the generation of an asymmetric center. Mitsunobu activation afforded

  本文报道了通过1，6-氮杂-迈克尔加成触发的序列和原始的Mitsunobu-类型一致的序列的有效的一锅多米诺过程，用于合成含有双-N，O-乙缩醛连接的四环系统。这种方法学导致了四个新键的构建，三个C–O键的断裂以及一个不对称中心的生成。Mitsunobu激活提供了最终的环闭合，涉及两个键的产生，这在报道的Mitsunobu类型序列中仍然是空前的。后者在具有挑战性的C 6下以区域选择性方式发生-吡啶酮中间体的-位置。在充分取代的对映体纯氨基醇的情况下，非对映异构体过量最多达到95：5。计算研究允许区分Mitsunobu序列的有利途径，并支持此步骤中观察到的区域选择性和非对映选择性。