1-Methyl-3',6'-dihydrospiro[indoline-3,2'-pyran]-2-one | 882041-44-3

• 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
• 英文名称: 1-Methyl-3',6'-dihydrospiro[indoline-3,2'-pyran]-2-one
• 英文别名: 1'-methylspiro[2,5-dihydropyran-6,3'-indole]-2'-one
• CAS: 882041-44-3
• 化学式: C₁₃H₁₃NO₂
• 分子量: 215.252
• InChiKey: XLPTVHMXHQSNRG-UHFFFAOYSA-N

物化性质

• 沸点：
  429.9±45.0 °C(predicted)
• 密度：
  1.26±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-allyl-3-hydroxy-1-methylindolin-2-one 在 Grubbs catalyst first generation sodium hydroxide 、 四丁基碘化铵 作用下， 以 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 21.0h， 生成 1-Methyl-3',6'-dihydrospiro[indoline-3,2'-pyran]-2-one
  参考文献：
  名称：

  Efficient Entry to Diversely Functionalized Spirocyclic Oxindoles from Isatins through Carbonyl-Addition/Cyclization Reaction Sequences

  摘要：

  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.

  DOI：

  10.1021/jo0525027

文献信息

• Photoinduced Synthesis of Functionalized Oxacyclic Spirooxindoles Via Ring Expansion
  作者：Dan Qi、Jinrui Bai、Zhuoheng Song、Bin Li、Chao Yang、Lin Guo、Wujiong Xia

  DOI：10.1021/acs.orglett.2c04218

  日期：2023.1.27

  A versatile photochemical ring-expansion protocol for the synthesis of oxacyclic spirooxindoles under catalyst-free conditions is described. The reaction is enabled by the use of unstrained O-containing heterocycles with 3-diazoindolin-2-ones under visible-light irradiation. Several synthetic advantages for this method are exhibited, including mild conditions, good functional group tolerance, operational

  描述了在无催化剂条件下合成 oxacyclic spirooxindoles 的多功能光化学扩环协议。该反应是通过在可见光照射下使用未应变的含 O 杂环和 3-二氮并吲哚-2-酮来实现的。展示了该方法的几个合成优势，包括温和的条件、良好的官能团耐受性、操作简单性和可扩展性。机理研究表明，转化可能通过氧鎓叶立德中间体的形成，然后是离子环化来进行。
• 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.