methyl 9-hydroxy-6,9-dihydropyrido[1,2-a]indole-8-carboxylate | 1246088-83-4

• 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: methyl 9-hydroxy-6,9-dihydropyrido[1,2-a]indole-8-carboxylate
• 英文别名: Methyl 9-hydroxy-6,9-dihydropyrido[1,2-a]indole-8-carboxylate
• CAS: 1246088-83-4
• 化学式: C₁₄H₁₃NO₃
• 分子量: 243.262
• InChiKey: RXTMJZSQDPUSAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  51.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  methyl 2-[(1-allyl-1H-indol-2-yl)(hydroxy)methyl]acrylate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以70%的产率得到methyl 9-hydroxy-6,9-dihydropyrido[1,2-a]indole-8-carboxylate
  参考文献：
  名称：

  Morita–Baylis–Hillman reaction of indole-2-carboxaldehyde: new vistas for indole-annulated systems

  摘要：

  DABCO-mediated Morita-Baylis-Hillman reactions of several 1-substituted-indole-2-carboxaldehydes are disclosed. It was discovered that carboethoxy or tert-butoxycarbonyl groups installed at N-1 undergo cleavage under the reaction conditions to afford 2-substituted indoles. Utility of the N-substituted adducts for preparing a variety of annulated indoles has been exemplified. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.07.078

文献信息

• Morita–Baylis–Hillman reaction of indole-2-carboxaldehyde: new vistas for indole-annulated systems
  作者：Subhasish Biswas、Virender Singh、Sanjay Batra

  DOI：10.1016/j.tet.2010.07.078

  日期：2010.9

  DABCO-mediated Morita-Baylis-Hillman reactions of several 1-substituted-indole-2-carboxaldehydes are disclosed. It was discovered that carboethoxy or tert-butoxycarbonyl groups installed at N-1 undergo cleavage under the reaction conditions to afford 2-substituted indoles. Utility of the N-substituted adducts for preparing a variety of annulated indoles has been exemplified. (C) 2010 Elsevier Ltd. All rights reserved.