6-fluoro-1H-indol-2-amine hydrochloride | 1262587-80-3

• 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: 6-fluoro-1H-indol-2-amine hydrochloride
• 英文别名: 2-Amino-6-fluoroindole hydrochloride；6-fluoro-1H-indol-2-amine;hydrochloride
• CAS: 1262587-80-3
• 化学式: C₈H₇FN₂*ClH
• 分子量: 186.616
• InChiKey: TZQAUCSWMKEDRD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.31
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.8
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-fluoro-1H-indol-2-amine hydrochloride 、 氯甲酸乙酯 在 碳酸氢钠 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 以67%的产率得到ethyl 2-[(ethoxycarbonyl)amino]-6-fluoro-1H-indole-1-carboxylate
  参考文献：
  名称：

  Three component tandem reactions involving protected 2-amino indoles, disubstituted propargyl alcohols, and I2/ICl: iodo-reactant controlled synthesis of dihydro-α-carbolines and α-carbolines via iodo-cyclization/iodo-cycloelimination

  摘要：

  Two simple, highly efficient three component tandem reactions for the synthesis of diversified N-a N-b dicarbamate-4,9-dihydro-3-iodo-alpha-carbolines and N-a-carbamate-3-iodo-alpha-carbolines have been described. The strategy involves one-pot condensation of bis-carbamate protected 2-amino indoles with disubstituted propargyl alcohols and I-2/ICl. The salient feature of the reaction involves iodocyclo-elimination of N-b-linked carbamate under mild condition in the final step. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.10.147

文献信息

• Three-Component Tandem Reaction Involving Acid Chlorides, Terminal Alkynes, and 2-Aminoindole Hydrochlorides: Synthesis of α-Carboline Derivatives in Aqueous Conditions via Regioselective [3 + 3] Cyclocondensation
  作者：Sahaj Gupta、Brijesh Kumar、Bijoy Kundu

  DOI：10.1021/jo201994v

  日期：2011.12.16

  An efficient synthesis toward highly diversified a-carboline derivatives via a three-component tandem reaction using acid chlorides, terminal allcynes, and 2-aminoindole hydrochlorides has been described. The salient feature of the one-pot strategy involves regioselective [3 + 3]-cyclocondensation and the presence of water in the reaction medium to facilitate cyclizafion. Nonaqueous conditions furnished products in poor yields.
• Three component tandem reactions involving protected 2-amino indoles, disubstituted propargyl alcohols, and I2/ICl: iodo-reactant controlled synthesis of dihydro-α-carbolines and α-carbolines via iodo-cyclization/iodo-cycloelimination
  作者：Sudhir K. Sharma、Sahaj Gupta、Mohammad Saifuddin、Anil K. Mandadapu、Piyush K. Agarwal、Harsh M. Gauniyal、Bijoy Kundu

  DOI：10.1016/j.tetlet.2010.10.147

  日期：2011.1

  Two simple, highly efficient three component tandem reactions for the synthesis of diversified N-a N-b dicarbamate-4,9-dihydro-3-iodo-alpha-carbolines and N-a-carbamate-3-iodo-alpha-carbolines have been described. The strategy involves one-pot condensation of bis-carbamate protected 2-amino indoles with disubstituted propargyl alcohols and I-2/ICl. The salient feature of the reaction involves iodocyclo-elimination of N-b-linked carbamate under mild condition in the final step. (C) 2010 Elsevier Ltd. All rights reserved.