3-ethyl-5-methoxy-2-methyl-1H-indole | 105902-05-4

• 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-ethyl-5-methoxy-2-methyl-1H-indole
• 英文别名: 3-ethyl-5-methoxy-2-methyl-indole；3-Aethyl-5-methoxy-2-methyl-indol
• CAS: 105902-05-4
• 化学式: C₁₂H₁₅NO
• 分子量: 189.257
• InChiKey: RLXPMDGXCPYADN-UHFFFAOYSA-N

物化性质

• 沸点：
  337.2±37.0 °C(Predicted)
• 密度：
  1.081±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  25
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-ethyl-5-methoxy-2-methyl-1H-indole 、 methyl 3-[[(methoxycarbonyl)imino]amino]but-2-enoate 在 zinc(II) chloride 作用下， 以 二氯甲烷 为溶剂， 以98%的产率得到(3aR*,8aS*)-methyl 3a-ethyl-5-methoxy-1-((methoxycarbonyl)amino)-2,8a-dimethyl-1,3a,8,8a-tetrahydropyrrolo[2,3-b]indole-3-carboxylate
  参考文献：
  名称：

  Synthesis of Polycyclic Fused Indoline Scaffolds through a Substrate-Guided Reactivity Switch

  摘要：

  Zn(II)-catalyzed divergent synthesis of functionalized polycyclic indolines through formal [3 + 2] and [4 + 2] cycloadditions of indoles with 1,2-diaza-1,3-dienes (DDs) is reported. The nature and type of substituents of substrates are found to act as a chemical switch to trigger two distinct reaction pathways and to obtain two different types of products upon the influence of the same catalyst. The mechanism of both [4 + 2] and [3 + 2] cycloadditions was investigated and fully rationalized by density functional theory (DFT) calculations.

  DOI：

  10.1021/acs.joc.0c01489
• 作为产物：
  描述：

  2-戊酮 、 α-Boc-1-(4-methoxyphenyl)-hydrazine 在 对甲苯磺酸 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以53%的产率得到3-ethyl-5-methoxy-2-methyl-1H-indole
  参考文献：
  名称：

  由N -Boc芳基肼方便地合成吲哚

  摘要：

  当与可烯醇化的酮反应时，容易获得的N- Boc芳基肼经过有效的Fischer环化反应，以高收率提供吲哚。

  DOI：

  10.1016/j.tetlet.2004.01.011

文献信息

• A Convenient Modification of the Fischer Indole Synthesis with a Solid Acid
  作者：Sosale Chandrasekhar、Somnath Mukherjee

  DOI：10.1080/00397911.2014.984854

  日期：2015.4.18

  the cation exchange resin Amberlite IR 120 in refluxing ethanol. A variety of enolizable aldehydes, and ketones and several substituted phenylhydrazines could thus be converted to the corresponding indoles in excellent yields (70–88%). Reaction times were typically 6–10 h, with the resin being then filtered off and the product isolated after minimal workup. GRAPHICAL ABSTRACT

  摘要 标题反应的新一锅版本包括在回流乙醇中加热羰基化合物、苯肼和阳离子交换树脂 Amberlite IR 120 的混合物。因此，各种可烯醇化的醛、酮和几种取代的苯肼可以以极好的收率（70-88%）转化为相应的吲哚。反应时间通常为 6-10 小时，然后将树脂过滤掉，并在最少的后处理后分离产物。图形概要
• Vejdelek, Collection of Czechoslovak Chemical Communications, 1957, vol. 22, p. 1852,1854
  作者：Vejdelek

  DOI：——

  日期：——
• A practical one-pot synthesis of 2,3-disubstituted indoles from unactivated anilines
  作者：Makoto Tokunaga、Mitsuru Ota、Masa-aki Haga、Yasuo Wakatsuki

  DOI：10.1016/s0040-4039(01)00588-3

  日期：2001.6

  2-Substituted-3-methyl indoles are synthesized with good regioselectivity from readily available substrates and catalysts, i.e. the reaction of anilines with propargyl alcohols in the presence of 0.36-1 mol% Ru-3(CO)(12). (C) 2001 Elsevier Science Ltd. All rights reserved.
• PROSTAGLANDIN RECEPTOR EP2 ANTAGONISTS, DERIVATIVES, AND USES RELATED THERETO
  申请人：Emory University

  公开号：US20220162186A1

  公开（公告）日：2022-05-26

  The disclosure relates to Prostnglandin receptor EP2 antagonists, derivatives, compositions, and methods related thereto. In certain embodiments, the disclosure relates to methods of treating or preventing conditions and diseases in which EP2 receptor activation has a physiological role, such as but not limited to, brain injury, inflammatory diseases, epilepsy, neuroinflammation after a seizure, pain, endometriosis, cancer, rheumatoid arthritis, skin inflammation, vascular inflammation, colitis, and neurological disorders by administering a pharmaceutical composition comprising a compound disclosed herein to a subject in need thereof.
• Synthesis of Polycyclic Fused Indoline Scaffolds through a Substrate-Guided Reactivity Switch
  作者：Cecilia Ciccolini、Giacomo Mari、Francesco G. Gatti、Giuseppe Gatti、Gianluca Giorgi、Fabio Mantellini、Gianfranco Favi

  DOI：10.1021/acs.joc.0c01489

  日期：2020.9.4

  Zn(II)-catalyzed divergent synthesis of functionalized polycyclic indolines through formal [3 + 2] and [4 + 2] cycloadditions of indoles with 1,2-diaza-1,3-dienes (DDs) is reported. The nature and type of substituents of substrates are found to act as a chemical switch to trigger two distinct reaction pathways and to obtain two different types of products upon the influence of the same catalyst. The mechanism of both [4 + 2] and [3 + 2] cycloadditions was investigated and fully rationalized by density functional theory (DFT) calculations.