3-methyl-2-pyrazol-1-yl-1H-indole | 1225067-97-9

• 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-methyl-2-pyrazol-1-yl-1H-indole
• 英文别名: 1-methyl-2-(1H-pyrazol-1-yl)-1H-indole；3-methyl-2-pyrazole-1-yl1H-indole
• CAS: 1225067-97-9
• 化学式: C₁₂H₁₁N₃
• 分子量: 197.239
• InChiKey: WFRWAGDGZZWNMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  33.6
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  吡唑 、 3-甲基吲哚 在 5-ethyl-1,3,7,8-tetramethylalloxazinium triflate 、 碘 、 氧气 作用下， 以 1,4-二氧六环 为溶剂， 50.0 ℃ 、101.33 kPa 条件下， 反应 72.0h， 以77%的产率得到3-methyl-2-pyrazol-1-yl-1H-indole
  参考文献：
  名称：

  吲哚的需氧氧化C–H偶氮化和黄素-碘偶联的有机催化一锅法合成氮唑基硫吲哚

  摘要：

  已开发了由黄素-碘偶联的有机催化驱动的吲哚与唑类的需氧氧化交叉偶联，用于2-（azol-1-yl）吲哚的绿色合成。偶联的有机催化系统通过利用分子氧作为唯一的牺牲试剂，以原子经济的方式从吲哚，唑类和硫醇一锅法合成2-偶氮基-3-硫代吲哚。

  DOI：

  10.1021/acs.orglett.1c00241

文献信息

• Iodine-Catalyzed Oxidative Cross-Coupling of Indoles and Azoles: Regioselective Synthesis of <i>N</i>-Linked 2-(Azol-1-yl)indole Derivatives
  作者：Danupat Beukeaw、Kwanchanok Udomsasporn、Sirilata Yotphan

  DOI：10.1021/jo502933e

  日期：2015.4.3

  A highly efficient iodine-catalyzed regioselective oxidative cross-coupling of an indole C-H bond and azole N-H bond is described. This metal-free reaction can be easily carried out at room temperature under mild and environmentally friendly conditions and provides a series of N-linked 2-(azol-1-yl)indole derivatives in moderate to excellence yields.
• Highly Regioselective C–N Bond Formation through C–H Azolation of Indoles Promoted by Iodine in Aqueous Media
  作者：Wen-Bin Wu、Jing-Mei Huang

  DOI：10.1021/ol302609m

  日期：2012.12.7

  An efficient and metal-free method for the direct C-N coupling of indoles with azoles to produce 2-(azol-1-yl)indoles in aqueous solution has been developed. This reaction proceeded highly regioselectively to provide a variety of indole derivatives with good to excellent yields.
• Metal-Free Coupling of Azoles with 2- and 3-Haloindoles Providing Access to Novel 2- or 3-(Azol-1-yl)indole Derivatives
  作者：Martin Poirier、Sébastien Goudreau、Jason Poulin、Jolaine Savoie、Pierre L. Beaulieu

  DOI：10.1021/ol100685p

  日期：2010.5.21

  Thermal or microwave-mediated heating of 2- or 3-haloindoles with azoles (pK(a) < 8) provides a straightforward, metal-free, and environmentally friendly access to novel 2-(azol-1-yl)indoles. Furthermore, previously unknown 2,3-bis(azolyl-1-yl)indoles can be prepared from 2,3-dihaloindoles by sequential reaction with two distinct azoles. This operationally simple acid-catalyzed process delivers novel indole derivatives in fair to excellent yields and expands the chemical diversity of substitutions that can be introduced on this medicinally important scaffold.
• Aerobic Oxidative C–H Azolation of Indoles and One-Pot Synthesis of Azolyl Thioindoles by Flavin–Iodine-Coupled Organocatalysis
  作者：Kazumasa Tanimoto、Hayaki Okai、Marina Oka、Ryoma Ohkado、Hiroki Iida

  DOI：10.1021/acs.orglett.1c00241

  日期：2021.3.19

  The aerobic oxidative cross-coupling of indoles with azoles driven by flavin-iodine-coupled organocatalysis has been developed for the green synthesis of 2-(azol-1-yl)indoles. The coupled organocatalytic system enabled the one-pot three-component synthesis of 2-azolyl-3-thioindoles from indoles, azoles, and thiols in an atom-economical manner by utilizing molecular oxygen as the only sacrificial reagent

  已开发了由黄素-碘偶联的有机催化驱动的吲哚与唑类的需氧氧化交叉偶联，用于2-（azol-1-yl）吲哚的绿色合成。偶联的有机催化系统通过利用分子氧作为唯一的牺牲试剂，以原子经济的方式从吲哚，唑类和硫醇一锅法合成2-偶氮基-3-硫代吲哚。