3-甲基-5H-螺[呋喃-2,3'-吲哚]-2'(1'H)-酮 | 882041-51-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 3-甲基-5H-螺[呋喃-2,3'-吲哚]-2'(1'H)-酮
• 中文别名: N2-苯基-N7-(3,4,5-三甲氧基苄基)噻唑[5,4-D]嘧啶-2,7-二胺
• 英文名称: 3-methyl-5H-spiro[furan-2,3'-indolin]-2'-one
• 英文别名: 3-Methyl-spiro[furan-2(5H),3'-[3H]indol]-2'(1'H)-one；4'-methylspiro[1H-indole-3,5'-2H-furan]-2-one
• CAS: 882041-51-2
• 化学式: C₁₂H₁₁NO₂
• 分子量: 201.225
• InChiKey: OARQBMWKFKUXMH-UHFFFAOYSA-N

物化性质

• 沸点：
  401.5±45.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-hydroxy-3-(1-methyl-propa-1,2-dienyl)-1,3-dihydro-indol-2-one 在 mercury (II) perchlorate trihydrate 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以80%的产率得到3-甲基-5H-螺[呋喃-2,3'-吲哚]-2'(1'H)-酮
  参考文献：
  名称：

  An Alternative to Precious Metals: Hg(ClO₄)₂·3H₂O as a Cheap and Water-Tolerant Catalyst for the Cycloisomerization of Allenols

  摘要：

  Hg(ClO4)(2)center dot 3H(2)O, a cheap, water-tolerant, and stable salt, catalyzes the cydoisomerization reaction or alpha-allenols to 2,5-dihydrofurans in an efficient and selective manner. The reaction is general and can be applied to differently functionalized substrates, including alkyl-substituted, aryl-substituted, enantiopure, and tertiary allenols. In addition, density functional theory (DFT) calculations were performed to obtain insight into various aspects of the controlled reactivity of a-allenols under mercury catalysis. They suggest a dual activation of the allenol by the Hg complex that drives the reaction to the chemoselective formation of 2,5-dihydrofurans.

  DOI：

  10.1021/acs.joc.5b00887

文献信息

• Efficient Entry to Diversely Functionalized Spirocyclic Oxindoles from Isatins through Carbonyl-Addition/Cyclization Reaction Sequences
  作者：Benito Alcaide、Pedro Almendros、Raquel Rodríguez-Acebes

  DOI：10.1021/jo0525027

  日期：2006.3.1

  A novel approach to diversely functionalized spirocyclic oxindoles has been developed by using different metal-mediated carbonyl-addition/cyclization reaction sequences. Spirocyclization precursors, 2-indolinonetethered homoallylic alcohols, (buta-1,3-dien-2-yl)methanols, and alpha-allenols have been obtained by regioselective addition of stabilized organoindium reagents to isatins in aqueous environment. Ruthenium-, silver-, and palladium-catalyzed reactions of the above unsaturated alcohol derivatives provided oxaspiro oxindoles.