5-Chloro-3-diazonio-1-[10-(2-formylphenoxy)decyl]indol-2-olate | 1296203-69-4

• 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-3-diazonio-1-[10-(2-formylphenoxy)decyl]indol-2-olate
• CAS: 1296203-69-4
• 化学式: C₂₅H₂₈ClN₃O₃
• 分子量: 453.969
• InChiKey: AYVBIHQARPNFRZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  32
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  82.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-Chloro-3-diazonio-1-[10-(2-formylphenoxy)decyl]indol-2-olate 在 dirhodium tetraacetate 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以68%的产率得到
  参考文献：
  名称：

  Demonstration of 14–20-membered intramolecular carbonyl ylides: diastereoselective synthesis of macrocycles incorporating spiro-indolooxiranes

  摘要：

  A range of macrocycles (13-19-membered) possessing spiro-indolooxirane unit were synthesized with complete diastereoselectivity in good yield by the rhodium(II) acetate catalyzed reaction of substituted cyclic diazoamides in dry dichloromethane. The reaction proceeds via the formation of the corresponding macrocyclic carbonyl ylide followed by a con-rotatory electrocyclization process. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.02.052
• 作为产物：
  描述：

  1,10-二溴癸烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 5-Chloro-3-diazonio-1-[10-(2-formylphenoxy)decyl]indol-2-olate
  参考文献：
  名称：

  Diastereoselective synthesis of macrocycles incorporating the spiro-indolofurans and -indolodioxolanes

  摘要：

  Generation of intramolecular macrocyclic carbonyl ylides from aldehyde group tethered to diazoamides in the presence of rhodium(II) acetate and their successful [3+2]-cycloaddition afforded the corresponding macrocycles incorporating spiro-indolofurans, -indolofuropyrroles, -indolofurofurans, and -indolodioxolanes in moderate to good yield with complete diastereoselectivity. The competition between the electrocyclization and [3+2]-cycloaddition reactions of macrocyclic carbonyl ylides was also demonstrated. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.12.020

文献信息

• Demonstration of 14–20-membered intramolecular carbonyl ylides: diastereoselective synthesis of macrocycles incorporating spiro-indolooxiranes
  作者：Sengodagounder Muthusamy、Thangaraju Karikalan、Eringathodi Suresh

  DOI：10.1016/j.tetlet.2011.02.052

  日期：2011.4

  A range of macrocycles (13-19-membered) possessing spiro-indolooxirane unit were synthesized with complete diastereoselectivity in good yield by the rhodium(II) acetate catalyzed reaction of substituted cyclic diazoamides in dry dichloromethane. The reaction proceeds via the formation of the corresponding macrocyclic carbonyl ylide followed by a con-rotatory electrocyclization process. (C) 2011 Elsevier Ltd. All rights reserved.
• Diastereoselective synthesis of macrocycles incorporating the spiro-indolofurans and -indolodioxolanes
  作者：Sengodagounder Muthusamy、Thangaraju Karikalan

  DOI：10.1016/j.tet.2011.12.020

  日期：2012.2

  Generation of intramolecular macrocyclic carbonyl ylides from aldehyde group tethered to diazoamides in the presence of rhodium(II) acetate and their successful [3+2]-cycloaddition afforded the corresponding macrocycles incorporating spiro-indolofurans, -indolofuropyrroles, -indolofurofurans, and -indolodioxolanes in moderate to good yield with complete diastereoselectivity. The competition between the electrocyclization and [3+2]-cycloaddition reactions of macrocyclic carbonyl ylides was also demonstrated. (C) 2011 Elsevier Ltd. All rights reserved.