2-butyl-5-nitro-1H-indole | 141645-66-1

• 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: 2-butyl-5-nitro-1H-indole
• 英文别名: 2-n-butyl 5-nitro indole
• CAS: 141645-66-1
• 化学式: C₁₂H₁₄N₂O₂
• 分子量: 218.255
• InChiKey: OPYVJLHNHMDRKU-UHFFFAOYSA-N

物化性质

• 熔点：
  99-101 °C
• 沸点：
  393.5±22.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  2-butyl-5-nitro-1H-indole 、 4-(3-chloropropoxy)benzoyl chloride 以 1,1-二氯乙烷 为溶剂， 以67.5%的产率得到3-[4-(3-chloropropoxy)benzoyl] 2-n-butyl 5-nitro indole
  参考文献：
  名称：

  Alkylaminoalkyl derivatives of benzofuran, benzothiophene, indole and

  摘要：

  该发明的主题是一般式的苯并呋喃、苯并噻吩、吲哚或吲哚啉化合物：##STR1##其中：Het代表以下其中之一的基团：##STR2##其中T、T'和T"特别代表一个基团：##STR3##R和R.sub.a，相同或不同，代表X代表--O--或--S--Y代表一个基团##STR4##这些化合物可用作药物，特别用于治疗心血管系统的病理综合征。

  公开号：

  US05223510A1
• 作为产物：
  描述：

  2-Hex-1-ynyl-4-nitroaniline 在 sodium hydroxide 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 0.33h， 生成 2-butyl-5-nitro-1H-indole
  参考文献：
  名称：

  Simple Indole Synthesis by One-Pot Sonogashira Coupling-NaOH-Mediated Cyclization

  摘要：

  在标准Sonogashira条件下，将o-碘苯胺与末端炔烃偶联，并在常规加热或微波辐照下进一步处理NaOH，通常可以获得高产率的2-取代吲哚。在反应条件下，卤素、硝基和氰基等功能团均可耐受。

  DOI：

  10.1055/s-0028-1083624

文献信息

• PtCl2-catalyzed reactions of o-alkynylanilines with ethyl propiolate and dimethyl acetylenedicarboxylate
  作者：Xun Li、Jun-Yan Wang、Wei Yu、Long-Min Wu

  DOI：10.1016/j.tet.2008.11.095

  日期：2009.2

  The PtCl2-catalyzed reactions between indoles and ethyl propiolate gave rise to mono and double addition products. The composition of the products was largely influenced by the substituents on the indoles as well as the amount of ethyl propiolate used. o-Alkynylanilines reacted with ethyl propiolate and dimethyl acetylenedicarboxylate under the catalysis of PtCl2 to generate the corresponding 2,3-disubstituted

  吲哚和丙酸乙酯之间的PtCl 2催化反应产生单加成产物和双加成产物。产物的组成在很大程度上受到吲哚上的取代基以及丙酸乙酯用量的影响。在PtCl 2的催化下，邻炔基苯胺与丙酸乙酯和乙酰二羧酸二甲酯反应，生成相应的2,3-二取代的吲哚。通过遵循顺序的环化/分子间加成途径来进行反应。
• Straightforward selective preparation of nitro- or amino-indoles from 2-halonitroanilines and alkynes. First synthesis of 7-amino-5-nitroindoles
  作者：Roberto Sanz、Verónica Guilarte、Antonio Pérez

  DOI：10.1016/j.tetlet.2009.05.027

  日期：2009.8

  A one-pot selective synthesis of 2-substituted C5-, C6-, and C7-nitro- or amino-indoles has been developed from 2-halonitroanilines. These two types of nitrogen-substituted indoles have been selectively obtained by only varying the solvent used in the tandem Sonogashira coupling/heteroannulation reaction. Moreover, from commercially available 2-bromo-4,6-dinitroaniline an unprecedented in situ selective reduction of one of the nitro groups has allowed the synthesis of new 7-amino-5-nitro-2-substituted indoles. (C) 2009 Elsevier Ltd. All rights reserved.
• Palladium-Catalyzed Direct 2-Alkylation of Indoles by Norbornene-Mediated Regioselective Cascade C–H Activation
  作者：Lei Jiao、Thorsten Bach

  DOI：10.1021/ja2055066

  日期：2011.8.24

  A palladium-catalyzed direct 2-alkylation reaction of free N-H indoles has been developed. This reaction relies on a norbornene-mediated cascade C-H activation process at the indole ring, which features high regioselectivity and excellent functional group, tolerance. The reaction represents the first example for a generally applicable, direct C-H alkylation of indole at the 2-position.
• Regioselective Direct C–H Alkylation of NH Indoles and Pyrroles by a Palladium/Norbornene-Cocatalyzed Process
  作者：Thorsten Bach、Lei Jiao

  DOI：10.1055/s-0033-1338523

  日期：——

  Nitrogen-containing heterocycles, including 1H-indoles and electron-deficient 1H-pyrroles, undergo a palladium/norbornene-cocatalyzed regioselective alkylation at the C-H bond adjacent to the NH group. A primary alkyl halide is used as the electrophile and the reaction proceeds smoothly under mild conditions to give 2-alkyl-1H-indoles and 2-substituted or 2,3-disubstituted 5-alkyl-1H-pyrroles in good yields.
• US5223510A
  申请人：——

  公开号：US5223510A

  公开（公告）日：1993-06-29