(2'R,3'R,6'R)-6'-(2-bromobenzyl)-1,3'-dimethyl-6',7'-dihydro-3'H-spiro[indoline-3,2'-oxepin]-2-one | 1175531-68-6

• 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: (2'R,3'R,6'R)-6'-(2-bromobenzyl)-1,3'-dimethyl-6',7'-dihydro-3'H-spiro[indoline-3,2'-oxepin]-2-one
• 英文别名: (3R,6R,7R)-3-[(2-bromophenyl)methyl]-1',6-dimethylspiro[3,6-dihydro-2H-oxepine-7,3'-indole]-2'-one
• CAS: 1175531-68-6
• 化学式: C₂₂H₂₂BrNO₂
• 分子量: 412.326
• InChiKey: BOICTXKEPQJKME-ZMPRRUGASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2'R,3'R,6'R)-6'-(2-bromobenzyl)-1,3'-dimethyl-6',7'-dihydro-3'H-spiro[indoline-3,2'-oxepin]-2-one 在 palladium diacetate 、 三乙胺 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以86%的产率得到(3R,5aR,10aR)-1',4-dimethyl-1,5a,10,10a-tetrahydrospiro[indeno[2,1-c]oxepine-3,3'-indolin]-2'-one
  参考文献：
  名称：

  Stereocontrolled Synthesis of Spirooxindoles through Lewis Acid-Promoted [5 + 2]-Annulation of Chiral Silyl Alcohols

  摘要：

  The enantioselective synthesis of stereochemically and structurally diverse spirocyclic oxindoles by [5 + 2]-annulation of chiral crotylsilanes bearing a primary alcohol is described. The annulation products were further elaborated to polycyclic oxindoles by Pd(0) catalysis.

  DOI：

  10.1021/ol901202t
• 作为产物：
  描述：

  (3,3-dimethoxy-N-methyl)indoline-2-one 、 (2S,3R,E)-2-(2-bromobenzyl)-3-(dimethyl(phenyl)silyl)hex-4-en-1-ol 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以60%的产率得到(2'R,3'R,6'R)-6'-(2-bromobenzyl)-1,3'-dimethyl-6',7'-dihydro-3'H-spiro[indoline-3,2'-oxepin]-2-one
  参考文献：
  名称：

  Stereocontrolled Synthesis of Spirooxindoles through Lewis Acid-Promoted [5 + 2]-Annulation of Chiral Silyl Alcohols

  摘要：

  The enantioselective synthesis of stereochemically and structurally diverse spirocyclic oxindoles by [5 + 2]-annulation of chiral crotylsilanes bearing a primary alcohol is described. The annulation products were further elaborated to polycyclic oxindoles by Pd(0) catalysis.

  DOI：

  10.1021/ol901202t

文献信息

• Stereocontrolled Synthesis of Spirooxindoles through Lewis Acid-Promoted [5 + 2]-Annulation of Chiral Silyl Alcohols
  作者：Yun Zhang、James S. Panek

  DOI：10.1021/ol901202t

  日期：2009.8.6

  The enantioselective synthesis of stereochemically and structurally diverse spirocyclic oxindoles by [5 + 2]-annulation of chiral crotylsilanes bearing a primary alcohol is described. The annulation products were further elaborated to polycyclic oxindoles by Pd(0) catalysis.