3-(4-甲氧基苯基)-4-苯基-2H-呋喃-5-酮 | 110836-03-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: 3-(4-甲氧基苯基)-4-苯基-2H-呋喃-5-酮
• 英文名称: 4-(4'-methoxyphenyl)-3-phenyl-2(5H)-furanone
• 英文别名: 4-(4-methoxyphenyl)-3-phenylfuran-2(5H)-one；4-(4-methoxyphenyl)-3-phenyl-5H-furan-2-one；3-(4-methoxyphenyl)-4-phenyl-2H-furan-5-one
• CAS: 110836-03-8
• 化学式: C₁₇H₁₄O₃
• 分子量: 266.296
• InChiKey: TVDQYUXHVNFJPQ-UHFFFAOYSA-N

物化性质

• 熔点：
  158-160 °C
• 沸点：
  472.1±45.0 °C(Predicted)
• 密度：
  1.222±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  3-(4-甲氧基苯基)-4-苯基-2H-呋喃-5-酮 在 叔丁基二甲硅基三氟甲磺酸酯 、 三溴化硼 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 58.0h， 生成
  参考文献：
  名称：

  부테놀라이드계 화합물과 그의 제조방법 및 그를 포함하는 약제학적 조성물

  摘要：

  This text is already in Korean. Would you like a translation into another language?

  公开号：

  KR101599426B1
• 作为产物：
  描述：

  p-methoxyphenacyl phenylacetate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 0.33h， 生成 3-(4-甲氧基苯基)-4-苯基-2H-呋喃-5-酮
  参考文献：
  名称：

  Design of Fluorine-Containing 3,4-Diarylfuran-2(5H)-ones as Selective COX-1 Inhibitors

  摘要：

  We report the design and synthesis of fluorine-containing cyclooxygenase-1 (COX-1)-selective inhibitors to serve as prototypes for the development of a COX-1-targeted imaging agent. Deletion of the SO2CH3 group of rofecoxib switches the compound from a COX-2- to a COX-1-selective inhibitor, providing a 3,4-diarylfuran-2(5H)-one scaffold for structureactivity relationship studies of COX-1 inhibition. A wide range of fluorine-containing 3,4-diarylfuran-2(5H)-ones were designed, synthesized, and tested for their ability to selectively inhibit COX-1 in purified protein and human cancer cell assays. Compounds containing a fluoro-substituent on the C-3 phenyl ring and a methoxy-substituent on the C-4 phenyl ring of the 3,4-diarylfuran-2(5H)-one scaffold were the best COX-1-selective agents of those evaluated, exhibiting IC(50)s in the submicromolar range. These compounds provide the foundation for development of an agent to facilitate radiologic imaging of ovarian cancer expressing elevated levels of COX-1.

  DOI：

  10.1021/ml500344j

文献信息

• One-Pot Synthesis of 3,4-Diaryl-Substituted 2(5<i>H</i>)-Furanone and Its Commercial Application
  作者：Anil Argade、Jigar Desai、Pravin Thombare、Kiran Shah、Sanjay Gite、Vijay Prajapati、Bipin Pandey、Mukul Jain、Pankaj Patel、Rajesh Bahekar

  DOI：10.1080/00397911.2011.577923

  日期：2012.11

  Abstract One-pot synthesis of 3,4-diaryl substituted 2(5H)-furanones was established and its commercial application has been demonstrated by accomplishing total synthesis of rofecoxib, under mild reaction conditions, with good yields and purity. GRAPHICAL ABSTRACT

  摘要 建立了3,4-二芳基取代的2(5H)-呋喃酮的一锅法合成方法，并通过完成罗非昔布的全合成，在温和的反应条件下，以良好的收率和纯度证明了其商业应用。图形概要
• Gold catalysed reactions with cyclopropenes
  作者：Jürgen T. Bauer、Maximillian S. Hadfield、Ai-Lan Lee

  DOI：10.1039/b815891f

  日期：——

  Gold(I) catalyses the ring-opening addition of cyclopropenes in a mild and regioselective manner.

  金(I)催化温和且区域选择性地促进环丙烯的环打开加成反应。
• Rh(i)-catalyzed CO gas-free cyclohydrocarbonylation of alkynes with formaldehyde to α,β-butenolides
  作者：Koji Fuji、Tsumoru Morimoto、Ken Tsutsumi、Kiyomi Kakiuchi

  DOI：10.1039/b503816b

  日期：——

  The rhodium(I)-catalyzed reaction of alkynes with formaldehyde proceeds via the double incorporation of a carbonyl moiety from formaldehyde, resulting in a CO gas-free cyclohydrocarbonylation leading to α,β-butenolides.

  铑(I)催化的炔烃与甲醛的反应通过双重引入甲醛中的羰基部分进行，产生无CO气体的环烃基化，最终生成α,β-丁内酯。
• Efficient direct asymmetric vinylogous Michael addition reactions of γ-butenolides to chalcones catalyzed by vicinal primary-diamine salts
  作者：Junfeng Wang、Chao Qi、Zemei Ge、Tieming Cheng、Runtao Li

  DOI：10.1039/b923925a

  日期：——

  The first direct organocatalytic asymmetric vinylogous Michael addition reactions of gamma-butenolides to chalcones have been developed by using chiral 1,2-diaminocyclohexane as a novel organocatalyst via a di-iminium transition state to provide syn-Michael products with good yields, high diastereoselectivities and enantioselectivities (up to 78% yield, >99 : 1 dr and 96% ee).

  通过使用手性的1,2-二氨基环己烷作为新型有机催化剂，通过二亚胺基过渡态，开发了γ-丁烯内酯与查耳酮的第一个直接有机催化不对称乙烯基乙烯基迈克尔加成反应，以提供具有高收率，高非对映选择性和对映选择性（产率高达78％，> 99：1 dr和96％ee）。
• Carbonylation of acetylenes under water gas shift conditions: a new method for synthesis of furan-2(5H)-ones
  作者：Kazuo Doyama、Takashi Joh、Kiyotaka Onitsuka、Tomoo Shiohara、Shigetoshi Takahashi

  DOI：10.1039/c39870000649

  日期：——

  Under water gas shift conditions acetylenes are selectively converted into furan-2(5H)-ones with catalysis by rhodium carbonyl clusters.

  在水煤气变换条件下，乙炔被羰基铑簇催化选择性地转化为呋喃-2（5 H）-1 。