5-(dimethylamino)-5-methyl-3,4-diphenyl-2(5H)-furanone | 143841-03-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 5-(dimethylamino)-5-methyl-3,4-diphenyl-2(5H)-furanone
• 英文别名: 5-(dimethylamino)-5-methyl-3,4-diphenylfuran-2(5H)-one；5-(dimethylamino)-5-methyl-3,4-diphenylfuran-2-one
• CAS: 143841-03-6
• 化学式: C₁₉H₁₉NO₂
• 分子量: 293.365
• InChiKey: LHOMKTSXZTXFPW-UHFFFAOYSA-N

物化性质

• 沸点：
  466.5±45.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.43
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  二苯基乙炔 、 alkaline earth salt of/the/ methylsulfuric acid 在 二环氧乙烷 作用下， 生成 5-(dimethylamino)-5-methyl-3,4-diphenyl-2(5H)-furanone
  参考文献：
  名称：

  Reaction of aminocarbene complexes of chromium with alkynes. 1. Formation and rearrangement of ketene and nitrogen ylide complexes

  摘要：

  The title reactions of chromium-containing carbene complexes (CO)5Cr=C(R1)N(R2R3) (R1 = H, Me, Ph; R2 = Me; R3 = Me, C3H5, CH2C3H5; R2R3 = (CH2)5) 8 and (CO)5Cr=C[(CH2)3C=CPh]N(R1R2) (R1 = R2 = Me; R1R2 = (CH2)5; R1R2 = (CH2)4) 9, bearing alkyl groups of low migratory aptitude on nitrogen, have been examined. In contrast to complexes in which nitrogen bears either an alkyl and an allyl or a benzyl group or is part of a strained cycle, which give heterocycles upon alkyne/CO insertions followed by nitrogen-to-carbon migrations (e.g., 1 --> 7), complexes 8 and 9 lead to stable nitrogen ylides, which could be fully characterized by X-ray crystallography in the case of 8a and 9a. Moreover, in the case of complexes of the general structure 9, ketene precursors of the ylides could either be detected (R1 = Me; R2 = CH2Ph) or isolated and characterized (R2R3 = (CH2)5). The new ylide complexes undergo, upon moderate heating, Stevens-type rearrangements to the expected heterocyclic compounds as a result of nitrogen-to-carbon migrations of various alkyl groups, and upon treatment with dimethyldioxirane, they undergo oxidation to lactone complexes.

  DOI：

  10.1021/ja00047a018

文献信息

• Silver-catalyzed ring-opening [3+2] annulation of cyclopropenones with amides
  作者：Takanori Matsuda、Yuki Tabata、Hirotsugu Suzuki

  DOI：10.1039/c8nj04579h

  日期：——

  A ring-opening [3+2] annulation reaction between cyclopropenones and amides was developed to produce 5-amino-2-furanones. Insertion of the carbonyl group of an amide to the C–C single bond of a cyclopropenone occurred efficiently in the presence of a catalytic amount of silver(I) triflate.

  环戊烯酮和酰胺之间的开环[3 + 2]环化反应被开发出来，生成5-氨基-2-呋喃酮。在催化量的三氟甲磺酸银（I）存在下，酰胺的羰基插入到环丙烯酮的CC单键中是有效的。
• Ag(I)-Catalyzed [3 + 2]-Annulation of Cyclopropenones and Formamides via C–C Bond Cleavage
  作者：Jiang-Tao Ren、Jia-Xin Wang、Hu Tian、Jing-Lei Xu、Hong Hu、Muhammad Aslam、Meng Sun

  DOI：10.1021/acs.orglett.8b02612

  日期：2018.11.2

  An unprecedented Ag-catalyzed [3 + 2]-annulation of cyclopropenones and DMF via C–C bond cleavage is disclosed. This protocol exhibited excellent chemo- and regio-selectivity, and tolerated various functional groups. More importantly, DMF served as the C═O bond in the cycloaddition reaction, providing an efficient way to construct γ-aminobutenolides. In addition, transesterification reaction occurred

  公开了一种前所未有的银催化通过CC键断裂的环丙烷和DMF [3 + 2]环化反应。该方案显示出优异的化学和区域选择性，并能耐受各种官能团。更重要的是，DMF在环加成反应中充当C = O键，为构建γ-氨基丁烯化物提供了一种有效的方法。另外，当DMF被酯取代时，发生酯交换反应。