3-FORMYL-1-METHYL-1H-INDOLE-2-CARBOXYLIC ACID | 174094-26-9

• 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-FORMYL-1-METHYL-1H-INDOLE-2-CARBOXYLIC ACID
• 英文别名: 3-formyl-1-methylindole-2-carboxylic acid
• CAS: 174094-26-9
• 化学式: C₁₁H₉NO₃
• mdl: MFCD07364736
• 分子量: 203.197
• InChiKey: XYANKXSPJQBIDM-UHFFFAOYSA-N

物化性质

• 沸点：
  449.2±30.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  59.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-FORMYL-1-METHYL-1H-INDOLE-2-CARBOXYLIC ACID 在 oxone||potassium monopersulfate triple salt 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 作用下， 以 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 7.5h， 生成 1,1'-dimethyl-5'-(trifluoromethoxy)-2,3'-spirobi[indoline]-2',3-dione
  参考文献：
  名称：

  Dearomative ipso-Cyclization to Spiropseudoindoxyls: An Extendable Approach To Access Indolo[3,2-c]quinolinones and Isocryptolepine

  摘要：

  DOI：

  10.1021/acs.orglett.3c03643
• 作为产物：
  描述：

  乙基3-甲酰基-1-甲基-1H-吲哚-2-羧酸酯 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 以90%的产率得到3-FORMYL-1-METHYL-1H-INDOLE-2-CARBOXYLIC ACID
  参考文献：
  名称：

  Indoles and pyridazino[4,5-b]indoles as nonnucleoside analog inhibitors of HIV-1 reverse transcriptase

  摘要：

  The synthesis and the study of the activity of new indol-2-carboxamides and pyridazino[4,5-b]indoles as inhibitors of HIV-1 reverse transcriptase (RT) are presented. The activity of the compounds synthesized as inhibitors of different types of HIV-1 RT (wild type enzyme and mutant forms P236L, Y181C and P236L/Y181C) was evaluated. The activity of the most active compounds was investigated in the syncytia reduction in vitro assay, in HIV-1(IIIB)-infected HT4lacZ-1 cells. Their potential cytotoxicity was determined in parallel. Two lead compounds, N-[1-[2-(3-isopropylamino)pyridyl]piperazin]-5,6-methylenedioxy indol-2-carboxamide 7q and N-[1-[2-(3-ethylamino)pyridyl]piperazin] 7s have been identified.

  DOI：

  10.1016/0223-5234(96)88316-4

文献信息

• Direct C-2 Carboxylation of 3-Substituted Indoles Using a Combined Brønsted Base Consisting of LiO-<i>t</i> Bu/CsF/18-crown-6
  作者：Masanori Shigeno、Itsuki Tohara、Kanako Nozawa-Kumada、Yoshinori Kondo

  DOI：10.1002/ejoc.202000272

  日期：2020.4.7

  A combination of LiO‐tBu, CsF, and 18‐crown‐6 can be used to carboxylate indole derivatives at the C‐2 position under an ambient CO2 atmosphere. Substrates bearing an electrophilic substituent (i.e. CN, formyl, benzoyl, phenylsulfonyl, phenylsulfinyl, and chloride) at the C‐3 position are smoothly converted into their corresponding carboxylated products with high functional group compatibility.

  LiO-的组合吨卜，CsF和18-冠-6可用于羧酸盐的环境CO下在C-2位的吲哚衍生物2的气氛。在C-3位置带有亲电取代基（例如CN，甲酰基，苯甲酰基，苯磺酰基，苯亚磺酰基和氯化物）的底物可以平滑地转化为具有高官能团相容性的相应羧化产物。
• Single Reactant Replacement Approach of Passerini Reaction: One-Pot Synthesis of β-Acyloxyamides and Phthalides
  作者：Yangyong Shen、Bo Huang、Linwei Zeng、Sunliang Cui

  DOI：10.1021/acs.orglett.7b02232

  日期：2017.9.1

  The Passerini reaction is a classical and well-known multicomponent reaction for accessing α-acyloxy amides. A single reactant replacement (SRR) approach of Passerini reaction is described, which involves aldehydes, carboxylic acids, and ynamides to constitute a one-pot synthesis of β-acyloxy amides in a convergent manner. When this method was subject to intramolecular reaction, the process would produce

  Passerini反应是用于获得α-酰氧基酰胺的经典且众所周知的多组分反应。描述了Passerini反应的单反应物置换（SRR）方法，该方法涉及醛，羧酸和乙酰胺，以收敛方式构成β-酰氧基酰胺的一锅法合成。当该方法进行分子内反应时，该过程将产生邻苯二甲酸酯产物。证明了可伸缩性，并进行了交叉反应以阐明合理的机制。