4-acetyl-5-methyl-3-phenylspiro[furan-2(3H),9'-xanthene] | 102860-83-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 4-acetyl-5-methyl-3-phenylspiro[furan-2(3H),9'-xanthene]
• 英文别名: 1-(5-methyl-3-phenylspiro[3H-furan-2,9'-xanthene]-4-yl)ethanone
• CAS: 102860-83-3
• 化学式: C₂₅H₂₀O₃
• 分子量: 368.432
• InChiKey: RZSPQZRLNGDHMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.16
• 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：

  4-acetyl-5-methyl-3-phenylspiro[furan-2(3H),9'-xanthene] 在 盐酸 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以12%的产率得到2-acetyl-3-methyl-1-phenylbenzo[kl]xanthene
  参考文献：
  名称：

  Photo-induced aromatic assembly of benzocycloalka[1,2-b] furan and spiro[furan-2(3H),1′-benzocycloalkane] derivatives

  摘要：

  The photo-induced benzannulation of benzocycloalka[1,2-b]furans produced hydrohelicene-type compounds ill good yields. A similar photoreaction of the spiro[furan-2(3H),1'-benzocycloalkane]s afforded dihydrophenalene derivatives in moderate yields. Benzo[kl]xanthene was also formed by a similar photoreaction of spiro[furan-2(3H),9'-xanthene]. The reaction pathway was elucidated by the H-1 NMR spectrum of the reaction mixture and the alternative synthesis of the intermediate. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.08.134
• 作为产物：
  描述：

  9-Benzylidene-9H-xanthene 、 乙酰丙酮 在 manganese triacetate 、 溶剂黄146 作用下， 反应 0.05h， 以19%的产率得到4-acetyl-5-methyl-3-phenylspiro[furan-2(3H),9'-xanthene]
  参考文献：
  名称：

  使用锰 (III) 介导的氧化自由基环化一锅法合成螺呋喃和苯并环烷[1,2-b]呋喃衍生物

  摘要：

  新的螺[furan-2(3H),1'-(benzocycloalkane)] 衍生物是通过在1,3-二羰基化合物存在下用乙酸锰(III) 氧化亚甲基苯并环烷烃获得的。苯并环烯烃衍生物的类似氧化以良好的收率产生了官能化的苯并环烷[1,2-b]呋喃。然而，l-benzyl-3,4-dihydronaphthalene 在相同的氧化条件下得到相应的螺呋喃和苯并环己[1,2-b]呋喃。还研究了螺呋喃和苯并环烷[1,2-b]呋喃的酸催化开环反应。

  DOI：

  10.1055/s-2005-861807

文献信息

• The Facile Synthesis of Dihydrofurans by the Oxidation of Olefins with Tris(2,4-pentanedionato)manganese(III)
  作者：Hiroshi Nishino

  DOI：10.1246/bcsj.58.1922

  日期：1985.7

  Eleven olefins were oxidized with tris(2,4-pentanedionato)manganese(III) at the reflux temperature to give the corresponding 3-acetyl-2-methyl-4,5-dihydrofurans in good yields. The oxidation of 9-benzylidene-9,10-dihydroanthracene under the same reaction conditions did not produce the corresponding dihydrofuran, but 9-[α-(1-acetyl-2-hydroxy-1-propenyl)benzylidene]-9,10-dihydroanthracene. When 1,1-diphenylethene

  在回流温度下用三(2,4-戊二酮)锰(III)氧化十一种烯烃，以良好的产率得到相应的3-乙酰基-2-甲基-4,5-二氢呋喃。9-苯亚甲基-9,10-二氢蒽在相同反应条件下氧化不产生相应的二氢呋喃，而是9-[α-(1-乙酰-2-羟基-1-丙烯基)苯亚甲基]-9,10-二氢蒽。当1,1-二苯基乙烯在室温下被氧化时，3-乙酰基-2-氢过氧-2-甲基-5,5-二苯基四氢呋喃以高产率获得。溶剂和添加剂对二氢呋喃收率的影响，其他（2,4-戊二酮）金属配合物的可比反应性，如 Co(III)、Cr(III)、Fe(III) 和 Cu(II) )，并讨论了反应机理。
• NISHINO, HIROSHI, BULL. CHEM. SOC. JAP., 1985, 58, N 7, 1922-1927
  作者：NISHINO, HIROSHI

  DOI：——

  日期：——
• One-Pot Synthesis of Spirofuran and Benzocycloalka[1,2-<i>b</i>]furan Derivatives Using Manganese(III)-Mediated Oxidative Radical Cyclization
  作者：Hiroshi Nishino、Reika Fujino

  DOI：10.1055/s-2005-861807

  日期：——

  obtained by the oxidation of methylenebenzocycloalkanes with manganese(III) acetate in the presence of 1,3-dicarbonyl compounds. A similar oxidation of the benzocycloalkene derivatives produced the functionalized benzocycloalka[1,2-b]furans in good yields. However, l-benzyl-3,4-dihydronaphthalene gave both the corresponding spirofuran and benzocyclohexa[1,2-b]furan under the same oxidation conditions.

  新的螺[furan-2(3H),1'-(benzocycloalkane)] 衍生物是通过在1,3-二羰基化合物存在下用乙酸锰(III) 氧化亚甲基苯并环烷烃获得的。苯并环烯烃衍生物的类似氧化以良好的收率产生了官能化的苯并环烷[1,2-b]呋喃。然而，l-benzyl-3,4-dihydronaphthalene 在相同的氧化条件下得到相应的螺呋喃和苯并环己[1,2-b]呋喃。还研究了螺呋喃和苯并环烷[1,2-b]呋喃的酸催化开环反应。
• Photo-induced aromatic assembly of benzocycloalka[1,2-b] furan and spiro[furan-2(3H),1′-benzocycloalkane] derivatives
  作者：Reika Fujino、Shougo Kajikawa、Hiroshi Nishino

  DOI：10.1016/j.tetlet.2005.08.134

  日期：2005.10

  The photo-induced benzannulation of benzocycloalka[1,2-b]furans produced hydrohelicene-type compounds ill good yields. A similar photoreaction of the spiro[furan-2(3H),1'-benzocycloalkane]s afforded dihydrophenalene derivatives in moderate yields. Benzo[kl]xanthene was also formed by a similar photoreaction of spiro[furan-2(3H),9'-xanthene]. The reaction pathway was elucidated by the H-1 NMR spectrum of the reaction mixture and the alternative synthesis of the intermediate. (c) 2005 Elsevier Ltd. All rights reserved.