1'-methyl-2'-oxospiro[cyclopropane-1,3'-indoline]-5'-carbonitrile | 1426228-10-5

• 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-2'-oxospiro[cyclopropane-1,3'-indoline]-5'-carbonitrile
• 英文别名: 1'-Methyl-2'-oxospiro[cyclopropane-1,3'-indoline]-5'-carbonitrile；1'-methyl-2'-oxospiro[cyclopropane-1,3'-indole]-5'-carbonitrile
• CAS: 1426228-10-5
• 化学式: C₁₂H₁₀N₂O
• 分子量: 198.224
• InChiKey: GOOUTISXYIQIJQ-UHFFFAOYSA-N

物化性质

• 沸点：
  479.9±45.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-氨基-3-溴苯腈 在 silver orthophosphate 、 palladium diacetate 、 sodium hydride 、 potassium carbonate 、 三环己基膦 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 35.25h， 生成 1'-methyl-2'-oxospiro[cyclopropane-1,3'-indoline]-5'-carbonitrile
  参考文献：
  名称：

  Silver-Promoted, Palladium-Catalyzed Direct Arylation of Cyclopropanes: Facile Access to Spiro 3,3′-Cyclopropyl Oxindoles

  摘要：

  The Pd-catalyzed, Ag(I)-mediated intramolecular direct arylation of cyclopropane C H bonds is described. Various spiro 3,3'-cyclopropyl oxindoles can be obtained in good to excellent yields from easily accessible 2-bromoanilides. The kinetic isotope effect was determined and epimerization studies were conducted, suggesting that the formation of a putative Pd-enolate is not operative and that the reaction proceeds via a C-H arylation pathway.

  DOI：

  10.1021/ol4003338

文献信息

• 10.1021/acs.orglett.4c01017
  作者：Hafeez, Saleem、Sharma, Ruchi、Jain, Swati、Sihag, Naveen、Bhartiya, Hemaang、Singh, Jitendra、Reddy, S. Rajagopala、Yadav, M Ramu

  DOI：10.1021/acs.orglett.4c01017

  日期：——

  We have demonstrated a Pd(0)-catalyzed Heck/C(sp3)–H activation cascade for the synthesis of spirocyclopropyl oxindoles in high yields from easily accessible ortho-bromoacrylamides. The formation of spirocyclopropyl oxindole is guided by an unconventional four-membered palladacycle through C(sp3)–H activation. The reaction exhibits a wide range of substrate scope and operates efficiently with a mere

  我们已经展示了 Pd(0) 催化的 Heck/C(sp 3 )–H 活化级联，用于从易于获得的邻溴丙烯酰胺中高产率合成螺环丙基羟吲哚。螺环丙基羟吲哚的形成是由非常规四元钯环通过 C(sp 3 )–H 活化引导的。该反应表现出广泛的底物范围，并且仅用 0.5 mol% 的 Pd 催化剂即可有效运行。此外，微波条件的使用有利于反应快速完成。此外，这种螺环丙烷化策略可以与[3 + 2]环加成结合产生螺吡咯烷羟吲哚，为制备(±)-horsfiline和(±)-coerulescine等生物碱提供了有价值的方法。
• Silver-Promoted, Palladium-Catalyzed Direct Arylation of Cyclopropanes: Facile Access to Spiro 3,3′-Cyclopropyl Oxindoles
  作者：Carolyn L. Ladd、Daniela Sustac Roman、André B. Charette

  DOI：10.1021/ol4003338

  日期：2013.3.15

  The Pd-catalyzed, Ag(I)-mediated intramolecular direct arylation of cyclopropane C H bonds is described. Various spiro 3,3'-cyclopropyl oxindoles can be obtained in good to excellent yields from easily accessible 2-bromoanilides. The kinetic isotope effect was determined and epimerization studies were conducted, suggesting that the formation of a putative Pd-enolate is not operative and that the reaction proceeds via a C-H arylation pathway.