4-methoxycarbonyl-5-methylspiro[furan-2(3H),1-(1',2',3',4'-tetrahydronaphthalene)]

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 4-methoxycarbonyl-5-methylspiro[furan-2(3H),1-(1',2',3',4'-tetrahydronaphthalene)]
• 英文别名: methyl 5-methyl-3',4'-dihydro-2'H,3H-spiro[furan-2,1'-naphthalene]-4-carboxylate；methyl 5'-methylspiro[2,3-dihydro-1H-naphthalene-4,2'-3H-furan]-4'-carboxylate
• 化学式: C₁₆H₁₈O₃
• 分子量: 258.317
• InChiKey: HWDWAUMPHCNCTG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 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-methoxycarbonyl-5-methylspiro[furan-2(3H),1-(1',2',3',4'-tetrahydronaphthalene)] 在 盐酸 作用下， 以 乙腈 为溶剂， 反应 18.0h， 以4%的产率得到5-acetyl-6-hydroxy-2,3-dihydrophenalene
  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：

  2-氯乙酰乙酸甲酯 、 1-methylene-1,2,3,4-tetrahydronaphthalene 在 fac-tris(2-phenylpyridinato-N,C2')iridium(III) 、 disodium hydrogenphosphate 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以57%的产率得到4-methoxycarbonyl-5-methylspiro[furan-2(3H),1-(1',2',3',4'-tetrahydronaphthalene)]
  参考文献：
  名称：

  二氢呋喃和β,γ-不饱和酮的化学发散光催化合成

  摘要：

  在可见光照射下由 Ir(ppy) 3催化的合成方法，用于从 α-卤代酮 ( 1 ) 和2,3-二氢呋喃 ( 3 ) 或 β,γ-不饱和酮 ( 7 )化学发散合成烯烃 ( 2 ) 已被开发。该过程的温和反应条件和氧化还原中性性质使其特别可持续，避免使用牺牲反应物和化学计量强氧化剂。在 DFT 计算的支持下，仔细的实验​​研究允许详细披露可能的机制途径，并将合成化学趋向于3或7，不仅取决于基材的性质，还取决于实验条件的选择。

  DOI：

  10.1002/adsc.202100260

文献信息

• 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。
• Chemodivergent Photocatalytic Synthesis of Dihydrofurans and β,γ‐Unsaturated Ketones
  作者：Arianna Quintavalla、Ruben Veronesi、Davide Carboni、Ada Martinelli、Nelsi Zaccheroni、Liviana Mummolo、Marco Lombardo

  DOI：10.1002/adsc.202100260

  日期：2021.7

  A synthetic procedure, catalysed by Ir(ppy)3 under visible-light irradiation, for the chemodivergent synthesis of 2,3-dihydrofurans (3) or β,γ-unsaturated ketones (7) starting from α-halo ketones (1) and alkenes (2) has been developed. The mild reaction conditions and the redox-neutral nature of the process make it particularly sustainable avoiding the use of both sacrificial reactants and stoichiometric

  在可见光照射下由 Ir(ppy) 3催化的合成方法，用于从 α-卤代酮 ( 1 ) 和2,3-二氢呋喃 ( 3 ) 或 β,γ-不饱和酮 ( 7 )化学发散合成烯烃 ( 2 ) 已被开发。该过程的温和反应条件和氧化还原中性性质使其特别可持续，避免使用牺牲反应物和化学计量强氧化剂。在 DFT 计算的支持下，仔细的实验​​研究允许详细披露可能的机制途径，并将合成化学趋向于3或7，不仅取决于基材的性质，还取决于实验条件的选择。
• 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.