3-(2-nitro-1-phenylpropyl)-1H-indole | 474012-86-7

• 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: 3-(2-nitro-1-phenylpropyl)-1H-indole
• 英文别名: 3-(2-nitro-1-phenyl-propyl)-indole；3-(2-Nitro-1-phenyl-propyl)-indol
• CAS: 474012-86-7
• 化学式: C₁₇H₁₆N₂O₂
• 分子量: 280.326
• InChiKey: FGLNQKZTSYEMLT-UHFFFAOYSA-N

物化性质

• 熔点：
  161-162 °C
• 沸点：
  482.2±40.0 °C(Predicted)
• 密度：
  1.228±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(2-nitro-1-phenylpropyl)-1H-indole 在 镍 一水合肼 作用下， 以 乙醇 为溶剂， 以90%的产率得到1-(1H-indol-3-yl)-1-phenyl-2-propylamine
  参考文献：
  名称：

  摘要：

  A new method was developed for the synthesis of alpha-alkyl- and alpha,alpha-dialkyl-beta-phenyl-tryptamines based on alkylation of nitroalkanes with alpha-phenyl-nor-gramine.

  DOI：

  10.1023/a:1015050806098
• 作为产物：
  描述：

  硝基乙烷 、 N-[1-H-indol-3-yl(phenyl)methyl]-N-methylamine 在 potassium carbonate 作用下， 以 乙醇 、 水 为溶剂， 以63%的产率得到3-(2-nitro-1-phenylpropyl)-1H-indole
  参考文献：
  名称：

  摘要：

  A new method was developed for the synthesis of alpha-alkyl- and alpha,alpha-dialkyl-beta-phenyl-tryptamines based on alkylation of nitroalkanes with alpha-phenyl-nor-gramine.

  DOI：

  10.1023/a:1015050806098

文献信息

• Efficient Preparation of 2-Indolyl-1-nitroalkane Derivatives Employing Nitroalkenes as Versatile Michael Acceptors:  New Practical Linear Approach to Alkyl 9<i>H</i>-β-Carboline-4-carboxylate
  作者：Giuseppe Bartoli、Marcella Bosco、Sandra Giuli、Arianna Giuliani、Laura Lucarelli、Enrico Marcantoni、Letizia Sambri、Elisabetta Torregiani

  DOI：10.1021/jo048776w

  日期：2005.3.1

  The combination of cerium(III) chloride heptahydrate and sodium iodide supported on silica gel is known to promote Michael-type additions. Continuing our work on solvent-free conditions, the CeCl3·7H2O−NaI−SiO2 system catalyzes the addition of a variety of indoles and nitroalkenes, giving 2-indolyl-1-nitroalkane derivatives in good yields. Development of this method has resulted in a new protocol for

  已知负载在硅胶上的七水合氯化铈（III）和碘化钠可促进迈克尔型添加。在无溶剂条件下继续我们的工作，CeCl 3 ·7H 2 O-NaI-SiO 2系统催化添加各种吲哚和硝基烯烃，从而以高收率得到2-吲哚基-1-硝基烷烃衍生物。该方法的发展为合成4-取代的β-咔啉提供了新的方法。
• Synthesis of 2-Indolyl-1-nitroalkane Derivatives Using Nanocrystalline Titanium(IV) Oxide
  作者：M. Lakshmi Kantam、Soumi Laha、Jagjit Yadav、P. Srinivas

  DOI：10.1080/00397910902883728

  日期：2009.10.21

  The catalytic Friedel-Crafts alkylation of indoles with nitroalkenes to furnish 2-indolyl-1-nitroalkane derivatives at room temperature with moderate to excellent yields is reported using nanocrystalline titanium(IV) oxide (nano-TiO2) catalyst. In all cases, a single regioisomer was obtained. After completion of the reaction, the catalyst was recovered by centrifugation and activated under a nitrogen flow for 1h at 250 degrees C for further reuse. The nano-TiO2 can be reused for four cycles with a slight decrease of activity under the same reaction conditions.
• The Reaction of Nitroölefins with Indole
  作者：Wayland E. Noland、Glenn M. Christensen、Gerald L. Sauer、G. G. S. Dutton

  DOI：10.1021/ja01607a070

  日期：1955.1
• ——
  作者：B. B. Semenov、Yu. I. Smushkevich

  DOI：10.1023/a:1015050806098

  日期：——

  A new method was developed for the synthesis of alpha-alkyl- and alpha,alpha-dialkyl-beta-phenyl-tryptamines based on alkylation of nitroalkanes with alpha-phenyl-nor-gramine.