ethyl 1'-methyl-2'-oxospiro[cyclopropane-1,3'-indoline]-5'-carboxylate | 1426228-09-2

• 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
• 英文名称: ethyl 1'-methyl-2'-oxospiro[cyclopropane-1,3'-indoline]-5'-carboxylate
• 英文别名: Ethyl 1'-methyl-2'-oxospiro[cyclopropane-1,3'-indole]-5'-carboxylate；ethyl 1'-methyl-2'-oxospiro[cyclopropane-1,3'-indole]-5'-carboxylate
• CAS: 1426228-09-2
• 化学式: C₁₄H₁₅NO₃
• 分子量: 245.278
• InChiKey: KYKUSMIEKNWRMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-氨基-3-溴苯甲酸乙酯 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 ethyl 1'-methyl-2'-oxospiro[cyclopropane-1,3'-indoline]-5'-carboxylate
  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

• 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.