11-(tert-butyl)chromeno[3',4':4,5]furo[2,3-b]indol-6(11H)-one | 1268158-60-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 11-(tert-butyl)chromeno[3',4':4,5]furo[2,3-b]indol-6(11H)-one
• 英文别名: 9-Tert-butyl-11,19-dioxa-9-azapentacyclo[10.8.0.02,10.03,8.013,18]icosa-1(12),2(10),3,5,7,13,15,17-octaen-20-one；9-tert-butyl-11,19-dioxa-9-azapentacyclo[10.8.0.02,10.03,8.013,18]icosa-1(12),2(10),3,5,7,13,15,17-octaen-20-one
• CAS: 1268158-60-6
• 化学式: C₂₁H₁₇NO₃
• 分子量: 331.371
• InChiKey: RNRGBOPVQCOIHR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  44.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(tert-butylamino)-3-(2-iodophenyl)-4H-furo[3,2-c]chromen-4-one 在 copper(l) iodide 、 potassium carbonate 、 L-脯氨酸 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以92%的产率得到11-(tert-butyl)chromeno[3',4':4,5]furo[2,3-b]indol-6(11H)-one
  参考文献：
  名称：

  I-MCR-Ullmann cascade toward furo[2,3-b]indole scaffold

  摘要：

  An efficient method for the construction of furo[2,3-b]indole derivatives 5 via an isocyanide-based multicomponent reaction (I-MCR) and a copper-catalyzed intramolecular Ullmann reaction sequence was described. This two-step sequence can be performed in a one-pot manner to produce the desired product 5 in moderate to good yield (up to 90%). (C) 2011 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2011.05.101

文献信息

• Tröger’s base derivative-catalyzed one-step one-pot synthesis of chromenofuroindoles and naphthofuroindoles
  作者：Hang Zhou、Ya-wen Sun、Jiang-biao Xu、Pei-yao Liang、Yu Wan、Rui Yuan、Hui Wu

  DOI：10.1007/s11164-022-04664-2

  日期：2022.4

  A series of N2,N8-bis(nitrogen-containing heterocycle)-yl-2,8-dicarboxamide-Tröger’s bases were synthesized. The most efficient one, N2,N8-di(4H-1,2,4-triazol-4-yl)-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine-2,8-dicarboxamide (4d), was used as bifunctional catalyst to promote the one-step one-pot preparation of the chromeno[3′,4′:4,5]furo[2,3-b]indoles or naphtho[2′,3′:4,5]furo[2,3-b]indoles with

  合成了一系列N 2 , N 8 -双(含氮杂环)-yl-2,8-二甲酰胺-Tröger碱。最有效的一种，N 2 , N 8 -di(4 H -1,2,4-triazol -4-yl)-6 H ,12 H -5,11-methanodibenzo[ b , f ][1,5] diazocine-2,8-dicarboxamide ( 4d )，用作双功能催化剂，促进色烯[3',4':4,5]呋喃[2,3- b ]吲哚的一步一锅法制备或萘[2',3':4,5]呋喃[2,3- b] 吲哚与 CuI 通过 4-羟基香豆素（或 2-羟基-1,4-萘醌）、取代的苯甲醛和异氰化物的级联 Aldol-[4 + 1] 环加成-分子内 Ullmann 反应。通过1 H NMR 滴定和对照实验研究了合理的催化机理。 图形概要
• I-MCR-Ullmann cascade toward furo[2,3-b]indole scaffold
  作者：Xu Zhu、Xiao-Ping Xu、Chang Sun、Tao Chen、Zhi-Liang Shen、Shun-Jun Ji

  DOI：10.1016/j.tet.2011.05.101

  日期：2011.8

  An efficient method for the construction of furo[2,3-b]indole derivatives 5 via an isocyanide-based multicomponent reaction (I-MCR) and a copper-catalyzed intramolecular Ullmann reaction sequence was described. This two-step sequence can be performed in a one-pot manner to produce the desired product 5 in moderate to good yield (up to 90%). (C) 2011 Published by Elsevier Ltd.