5-二苯基亚甲基-2(5H)-呋喃酮 | 18812-36-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 5-二苯基亚甲基-2(5H)-呋喃酮
• 英文名称: 5-diphenylmethylene-2(5H)-furanone
• 英文别名: 5-benzhydrylidene-5H-furan-2-one；5-Benzhydryliden-5H-furan-2-on；5-(Diphenylmethylene)furan-2(5H)-one；5-benzhydrylidenefuran-2-one
• CAS: 18812-36-7
• 化学式: C₁₇H₁₂O₂
• 分子量: 248.281
• InChiKey: IEHHVHWZADMUNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-二苯基亚甲基-2(5H)-呋喃酮 在 溴 、 三乙胺 作用下， 以 乙醚 为溶剂， 反应 5.0h， 以81%的产率得到5-benzhydrylidene-3-bromo-5H-furan-2-one
  参考文献：
  名称：

  Synthesis and evaluation of novel furanones as biofilm inhibitors in opportunistic human pathogens

  摘要：

  DOI：

  10.1016/j.ejmech.2022.114678
• 作为产物：
  描述：

  ethyl 5-chloro-2-fuorate 、 phenylmagnesium bromide 在 乙醚 作用下， 生成 5-二苯基亚甲基-2(5H)-呋喃酮
  参考文献：
  名称：

  Decomposition of 5-Halogeno-2-furylmethyl Ethers to Benzalcrotonolactones

  摘要：

  DOI：

  10.1021/ja01157a001

文献信息

• METHYLENE FURANONE DERIVATIVES AND USE OF SAID DERIVATIVES AS A PHOTOPROTECTING OR ANTIOXIDANT OR DEPIGMENTATION AGENT IN COSMETIC OR DERMATOLOGICAL COMPOSITIONS
  申请人：Marchal Estelle

  公开号：US20110184059A1

  公开（公告）日：2011-07-28

  The present invention relates to novel methylene furanone derivatives as well as the use thereof as a protective, antioxidant, or depigmentation agent in cosmetic or dermatological compositions. The invention also relates to a method for preparing said derivatives involving a Suzuki-Miyaura coupling reaction from corresponding dibromofuranone derivatives. The invention also relates to a method of preparation involving a coupling reaction of 2-methoxy-furan derivatives with a ketone followed by dehydration.

  本发明涉及新型亚甲基呋喃酮衍生物，以及其作为化妆品或皮肤科组合物中的保护剂、抗氧化剂或脱色剂的用途。该发明还涉及一种制备所述衍生物的方法，涉及从相应的二溴呋喃酮衍生物中进行Suzuki-Miyaura偶联反应的方法。该发明还涉及一种涉及2-甲氧基呋喃衍生物与酮进行偶联反应，然后脱水的制备方法。
• A new synthesis of 5-methylene-2(5H)-furanone derivatives
  作者：Roberto Antonioletti、Maurizio D'Auria、Antonella De Mico、Giovanni Piancatelli、Arrigo Scettri

  DOI：10.1016/s0040-4020(01)88810-4

  日期：1984.1

  5-methylene-2(5H)-furanone derivatives are easily obtained by treatment of tertiary 2-furylcarbinols with pyridinium dichromate in dimethylformamide solution. Through this procedure, a natural product, the thiophene lactone isolated from Chamaemelum Nobile L., has been synthesized.

  通过在二甲基甲酰胺溶液中用重铬酸吡啶鎓处理叔2-呋喃基甲醇，可以轻松获得5-亚甲基-2（5H）-呋喃酮衍生物。通过该步骤，已经合成了从Chamaemelum Nobile L.分离的噻吩内酯的天然产物。
• Synthesis and Reactivity of Dihalofuranones
  作者：Timothy P. O'Sullivan、Thérèse A. Lyons、Cormac G.M. Gahan

  DOI：10.2174/1570178618666211027103633

  日期：2022.8

  Halogenated furanones have been found to act as potent quorum sensing inhibitors in several bacterial species. It is believed that dihalofuranones covalently bind to the LuxS enzyme, which is necessary for autoinducer-2 synthesis. In addition to their antimicrobial activity, halogenated furanones also possess anti-cancer, antioxidant, and depigmentation properties. However, traditional routes to these compounds are low-yielding and capricious.

  The aim of this study was to investigate higher-yielding preparations of gemdihalofuranones and compare their reactivity using Suzuki chemistry.

  Ramirez dibromoolefination of maleic anhydride was optimised using a variety of conditions. A similar route was investigated for the preparation of bromofluorofuranones and dichlorofuranones. The conversion of a dichlorofuranone to the corresponding iodofuranone derivatives using microwave-assisted Finkelstein chemistry was also studied. Lastly, the reactivity of the different dihalofuranones was compared by Pd-mediated coupling with phenylboronic acid.

  A higher-yielding, concise synthesis of dibromofuranones was developed using a modified Ramirez reaction. Additionally, a telescoped preparation of dichlorofuranone was higher yielding than previous approaches. Bromine- and iodine-substituted dihalofuranones proved more reactive than their chlorine-substituted analogues.

  Higher yielding routes to bromine-, fluorine-, chlorine- and iodine-containing dihalofuranones were successfully developed. Suzuki couplings of gem-dihalofuranones were found to proceed with high stereoselectivity.

  背景：已经发现卤代呋喃酮在几种细菌物种中作为强力的群体感应抑制剂。据信二卤代呋喃酮与LuxS酶共价结合，后者对于自发诱导素-2的合成是必需的。除了它们的抗微生物活性外，卤代呋喃酮还具有抗癌、抗氧化和美白的特性。然而，传统的合成这些化合物的方法产率低且难以控制。 目的：本研究旨在研究高产率的制备双卤代呋喃酮，并比较它们在铃木化学中的反应性。 方法：通过使用各种条件来优化Ramirez二溴代烯丙酸酐的制备。还研究了类似的方法来制备溴氟代呋喃酮和二氯代呋喃酮。还研究了使用微波辅助的Finkelstein化学方法将二氯代呋喃酮转化为相应的碘代呋喃酮衍生物。最后，通过Pd介导的与苯基硼酸的偶联反应比较了不同双卤代呋喃酮的反应性。 结果：使用改进的Ramirez反应开发了高产率、简洁的二溴代呋喃酮合成方法。此外，望远镜式的二氯代呋喃酮制备方法比以前的方法产率更高。溴和碘取代的双卤代呋喃酮比其氯取代的类似物更具反应性。 结论：成功地开发了制备含溴、氟、氯和碘的双卤代呋喃酮的高产率路线。发现宝石双卤代呋喃酮的铃木偶联反应具有高立体选择性。
• ANTONIOLETTI, R.;DAURIA, M.;DE, MICO, A.;PIANCATELLI, G.;SCETTRI, A., TETRAHEDRON, 1984, 40, N 19, 3805-3808
  作者：ANTONIOLETTI, R.、DAURIA, M.、DE, MICO, A.、PIANCATELLI, G.、SCETTRI, A.

  DOI：——

  日期：——
• DERIVES DE METHYLENE FURANONE ET UTILISATION DE CES DERIVES EN TANT QU'AGENT PHOTOPROTECTEUR OU ANTIOXYDANT OU DEPIGMENTANT DANS DES COMPOSITIONS A USAGE COSMETIQUE OU DERMATOLOGIQUE.
  申请人：Pierre Fabre Dermo-Cosmétique

  公开号：EP2350036A1

  公开（公告）日：2011-08-03