5'-chloro-1',3-dimethyl-5H-spiro[furan-2,3'-indolin]-2'-one | 1370346-95-4

• 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: 5'-chloro-1',3-dimethyl-5H-spiro[furan-2,3'-indolin]-2'-one
• 英文别名: 5'-chloro-1',4-dimethylspiro[2H-furan-5,3'-indole]-2'-one
• CAS: 1370346-95-4
• 化学式: C₁₃H₁₂ClNO₂
• 分子量: 249.697
• InChiKey: LZXSVRAFDMXHGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 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：

  在 4-溴苯酚 、 四丁基溴化铵 、 potassium carbonate 、 palladium dichloride 作用下， 以 水 为溶剂， 反应 1.5h， 以59%的产率得到5'-chloro-1',3-dimethyl-5H-spiro[furan-2,3'-indolin]-2'-one
  参考文献：
  名称：

  水中的钯纳米粒子：可重复使用的催化体系，用于α-烯丙醇的环醚化或苯环化

  摘要：

  已经开发了一种便捷的无配体催化体系，用于在水性反应介质中通过钯纳米粒子（PdNP）对各种α-烯醇衍生物进行化学选择性环化反应。

  DOI：

  10.1002/adsc.201501132

文献信息

• Ring Enlargement versus Selenoetherification on the Reaction of Allenyl Oxindoles with Selenenylating Reagents
  作者：Benito Alcaide、Pedro Almendros、Amparo Luna、Gonzalo Gómez-Campillos、M. Rosario Torres

  DOI：10.1021/jo202495z

  日期：2012.4.6

  Lactam-tethered allenols, readily prepared from α-oxolactams, were used as starting materials for divergent reactivity with selenenylating reagents. Either oxycyclization (spirocyclic selenolactams) or ring expansion (selenoquinolones) can be achieved through the choice of both reagents and substrates. The biological activity of some of the synthesized heterocycles has additionally been evaluated in four human

  容易由α-氧代内酰胺制备的内酰胺束缚的烯丙醇用作起始原料，用于与硒烯化试剂发生发散反应。氧环化（螺环硒内酰胺）或环扩环（硒代喹诺酮）均可通过选择试剂和底物来实现。另外，已经在四种人类癌细胞系中评估了某些合成杂环的生物活性。
• An Alternative to Precious Metals: Hg(ClO₄)₂·3H₂O as a Cheap and Water-Tolerant Catalyst for the Cycloisomerization of Allenols
  作者：Benito Alcaide、Pedro Almendros、Amparo Luna、Elena Soriano

  DOI：10.1021/acs.joc.5b00887

  日期：2015.7.17

  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.
• Palladium Nanoparticles in Water: A Reusable Catalytic System for the Cycloetherification or Benzannulation of α-Allenols
  作者：Benito Alcaide、Pedro Almendros、Ana M. González、Amparo Luna、Sagrario Martínez-Ramírez

  DOI：10.1002/adsc.201501132

  日期：2016.6.16

  A convenient ligand‐free catalytic system has been developed for the chemoselective cyclization reaction of various α‐allenol derivatives by palladium nanoparticles (PdNPs) in an aqueous reaction medium.

  已经开发了一种便捷的无配体催化体系，用于在水性反应介质中通过钯纳米粒子（PdNP）对各种α-烯醇衍生物进行化学选择性环化反应。