benzofuran-3-yl(phenyl)methanone | 6454-01-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzofuran-3-yl(phenyl)methanone
• 英文别名: 3-benzoyl benzofuran；3-benzoylbenzofuran；benzofuran-3-yl-phenyl-methanone；benzofuran-3-yl-phenyl ketone；Benzofuran-3-yl-phenyl-keton；Phenyl--keton；1-Benzofuran-3-yl(phenyl)methanone
• CAS: 6454-01-9
• 化学式: C₁₅H₁₀O₂
• 分子量: 222.243
• InChiKey: TWWAVGXQPVEBKZ-UHFFFAOYSA-N

物化性质

• 熔点：
  65 °C
• 沸点：
  200-201 °C(Press: 11 Torr)
• 密度：
  1.204±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  benzofuran-3-yl(phenyl)methanone 在 camphor-10-sulfonic acid 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 3-(2-phenylbenzofuran-3-yl)propanenitrile
  参考文献：
  名称：

  Interrupting Base-Mediated Benzofuran Ring Transformation with Michael Acceptors

  摘要：

  A simple two-stage approach for the synthesis of 3-(2-arylbenzofuran-3-yl)propanoates and propanamides has been developed employing simple acrylates and acrylamides and readily available 3-aroylbenzofurans. The key step of this process involves a base-mediated ring opening of the 3-aroylbenzofurans and subsequent Michael addition of the resulting 1,3-dicarbonyl intermediate with acrylate/acrylamide, followed by the deformylation in one-pot. The resulting products undergo an acid-mediated dehydrative cyclization to arrive at these targets.

  DOI：

  10.1021/acs.joc.7b01267
• 作为产物：
  描述：

  3-溴-1-苯并呋喃 在 吡啶 作用下， 生成 benzofuran-3-yl(phenyl)methanone
  参考文献：
  名称：

  Martynoff, Bulletin de la Societe Chimique de France, 1952, p. 1056,1060

  摘要：

  DOI：

文献信息

• Synthesis of carbonylated heteroaromatic compounds via visible-light-driven intramolecular decarboxylative cyclization of o-alkynylated carboxylic acids
  作者：Fei Gao、Jiu-Tao Wang、Lin-Lin Liu、Na Ma、Chao Yang、Yuan Gao、Wujiong Xia

  DOI：10.1039/c7cc04813k

  日期：——

  An efficient strategy for the easy access to carbonylated heteroaromatic compounds has been developed via a visible-light-promoted intramolecular decarboxylative cyclization reaction of o-alkynylated carboxylic acids. This method is characterized by its benign conditions and the tolerance to a wide range of functionalities.

  已经通过可见光促进了邻炔基化羧酸的分子内脱羧环化反应，开发了一种易于获得羰基杂芳族化合物的有效策略。该方法的特点是其良性条件和对多种功能的耐受性。
• Electronic Control on Linear versus Branched Alkylation of 2-/3-Aroylbenzofurans with Acrylates: Combined DFT and Synthetic Studies
  作者：Kolluru Srinivas、Yuvraj Dangat、Yadagiri Kommagalla、Kumar Vanka、Chepuri V. Ramana

  DOI：10.1002/chem.201700643

  日期：2017.6.1

  synergistic operation of the steric and electronic effects favoring the branched alkylation. Further DFT investigations on the alkylation of the isomeric 3‐aroylbenzofurans indicated a preference for the linear alkylation and this has been verified experimentally. Overall, the observed/calculated complementary selectivity in the alkylation of 2‐/3‐aroylbenzofurans with acrylates reveals that the substrate‐dependent

  通过计算与两个关键步骤相关的动力学（丙烯酸酯与中间钌环的配位），研究了控制2-芳基苯并呋喃与丙烯酸酯通过丙烯酸催化的羰基化CH活化的异常支化烷基化的因素。以及随后的迁移插入反应-借助DFT计算进行了研究。计算中考虑了每种烷基化方式的八个可能的方向。从这些计算中，已经理解，存在有利于支链烷基化的空间效应和电子效应的协同作用。DFT对异构3-芳基苯并呋喃的烷基化的进一步研究表明，偏爱线性烷基化，这一点已通过实验进行了验证。全面的，
• A novel efficient protocol for preparation of 3-formyl-2-arylbenzo[b]furan derivatives
  作者：Benren Liao、Libo Ruan、Min Shi、Nian Li、Liang Chang、Leping Liu、Fan Yang、Jie Tang

  DOI：10.1016/j.tetlet.2014.04.050

  日期：2014.5

  An efficient method for preparation of 3-formyl-2-arylbenzo[b]furan derivatives 4 from 3-chloro-2-(2-methoxyaryl)-1-arylprop-2-en-1-one 2 was developed, and the desired product was obtained in good to excellent yields. By converting 2-(2-methoxyphenyl)-3-oxo-3-phenylpropanal 1 to 2, the regioselectivity problem occurring in the reaction when using 1 as the starting material was successfully avoided

  用于制备3-甲酰基-2-芳基苯并[的有效方法b ]呋喃衍生物4，由3-氯-2-（2- methoxyaryl）-1- arylprop -2-烯-1-酮2开发，以及所需的获得的产物具有良好至优异的产率。通过将2-（2-甲氧基苯基）-3-氧代-3-苯基丙醛1转化为2，成功地避免了当使用1作为起始原料时在反应中发生的区域选择性问题。此外，尽管形成了中间体3-（二溴甲基）-2-苯基苯并[ b ]呋喃3a，但仍采用了一锅法进行连续的脱甲基，环化和水解反应可能是孤立的。在一些现场调查的基础上，提出了一种可行的机制。
• Phenyl oxo-acetic acids useful in the treatment of insulin resistance and hyperglycemia
  申请人：Wyeth

  公开号：US20040102480A1

  公开（公告）日：2004-05-27

  This invention provides compounds of Formula I having the structure 1 wherein: A is O, S, or N; B is —(CH 2 ) m —, —CH(OH)—, or carbonyl; R 1 is hydrogen, halogen, alkyl of 1-6 carbon atoms, alkoxy of 1-6 carbon atoms, or trifluoromethyl; R 2 is alkyl of 1-18 carbon atoms, aryl of 6-10 carbon atoms, arylalkyl of 7-15 carbon atoms, Het-alkyl wherein the alkyl moiety is 1-6 carbon atoms; Het is 2 R 2a is alkylene of 1-3 carbon atoms; G is oxygen, sulfur, or nitrogen; R 3 , R 4 are each, independently, hydrogen, halogen, alkyl of 1-3 carbon atoms, aryl of 6-10 carbon atoms or a heterocyclic ring of 5 to 7 ring atom containing 1 to 3 heteroatoms selected from oxygen, nitrogen, sulfur; R 5 is hydrogen, alkyl of 1-6 carbon atoms, —CH(R 7 )R 8 , —C(CH 2 ) n CO 2 R 9 , —C(CH 3 ) 2 CO 2 R 9 , —CH(R 7 )(CH 2 ) n CO 2 R 9 , or CH(R 7 )C 6 H 4 CO 2 R 9 ; R 6 is hydrogen, halogen, alkyl of 1-6 carbon atoms, or —OR 5 ; m=1-6; n=1-6; R 7 is hydrogen, alkyl of 1-6 carbon atoms, aryl of 6-10 carbon atoms, or arylalkyl of 7-15 carbon atoms; R 8 is —CO 2 R 10 , —CONHR 10 , tetrazole, or —PO 3 ; R 9 and R 10 are each, independently, hydrogen, alkyl of 1-6 carbon atoms, aryl of 6-10 carbon atoms, or arylalkyl of 7-15 carbon atoms; or a pharmaceutically acceptable salt thereof, which are useful in treating metabolic disorders related to insulin resistance or hyperglycemia.

  该发明提供了具有结构式I的化合物，其中：A为O、S或N；B为—(CH2)m—、—CH(OH)—或羰基；R1为氢、卤素、1-6个碳原子的烷基、1-6个碳原子的烷氧基或三氟甲基；R2为1-18个碳原子的烷基、6-10个碳原子的芳基、7-15个碳原子的芳基烷基、Het-alkyl，其中烷基部分为1-6个碳原子；Het为2R2a为1-3个碳原子的烷基；G为氧、硫或氮；R3、R4分别独立地为氢、卤素、1-3个碳原子的烷基、6-10个碳原子的芳基或含有1-3个杂原子（选自氧、氮、硫）的5至7个环原子的杂环；R5为氢、1-6个碳原子的烷基、—CH(R7)R8、—C(CH2)nCO2R9、—C(CH3)2CO2R9、—CH(R7)(CH2)nCO2R9或CH(R7)C6H4CO2R9；R6为氢、卤素、1-6个碳原子的烷基或—OR5；m=1-6；n=1-6；R7为氢、1-6个碳原子的烷基、6-10个碳原子的芳基或7-15个碳原子的芳基烷基；R8为—CO2R10、—CONHR10、四唑或—PO3；R9和R10各自独立地为氢、1-6个碳原子的烷基、6-10个碳原子的芳基或7-15个碳原子的芳基烷基；或其药学上可接受的盐，用于治疗与胰岛素抵抗或高血糖有关的代谢障碍。
• A Sustainable and Versatile Cellulose‐based CO Surrogate for Carbonylative Reactions
  作者：You Wang、Bing Tian、Yi Li、Wei Li、Zhijun Chen、Shouxin Liu、Shujun Li

  DOI：10.1002/cssc.202301324

  日期：——

  The highly toxic and flammable nature of CO lead to high handling demand for its use and storage, undoubtedly constricting its further academic exploration for carbonylative reactions in laboratory. Although many CO surrogates have been developed and applied in carbonylative reactions instead of CO gas, exploration of more versatile CO surrogates for diverse carbonylations is still highly desirable. Here we report a cellulose‐based CO surrogate (cellulose‐CO), which prepared from cheap and abundant cellulose through a simple and green process. The very mild and efficient CO release makes this reagent a highly competitive candidate for providing CO in carbonylation. This surrogate is compatible with a wide variety of functional groups in various carbonylative reactions due to the excellent compatibility of cellulose‐CO. Moreover, the cellulose‐CO exhibits excellent chemical stability which can be stored exposed to air for 12 months, making this CO surrogate a robust and general reagent in CO chemistry.

  摘要 CO 的高毒性和易燃性导致对其使用和储存的处理要求很高，这无疑限制了学术界对其在实验室羰基化反应中的进一步探索。尽管已经开发了许多 CO 代用品并将其应用于替代 CO 气体的羰基化反应中，但探索更多功能的 CO 代用品用于多种羰基化反应仍然是非常必要的。在此，我们报告了一种基于纤维素的 CO 代用品（纤维素-CO），它由廉价而丰富的纤维素通过简单的绿色工艺制备而成。这种试剂能非常温和、高效地释放 CO，是羰基化过程中提供 CO 的极具竞争力的候选试剂。由于纤维素-CO 具有出色的兼容性，这种代用试剂在各种羰基化反应中可与多种官能团兼容。此外，纤维素-CO 还具有极佳的化学稳定性，可暴露在空气中保存 12 个月，使这种 CO 代用试剂成为 CO 化学反应中一种坚固耐用的通用试剂。