5-氟-3-甲基-1H-吲哚-2-甲醛 | 842972-09-2

• 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
• 中文名称: 5-氟-3-甲基-1H-吲哚-2-甲醛
• 中文别名: 5-氟-3-甲基-1H-1H-吲哚-2-甲醛
• 英文名称: 5-fluoro-3-methyl-1H-indole-2-carbaldehyde
• CAS: 842972-09-2
• 化学式: C₁₀H₈FNO
• mdl: MFCD06011083
• 分子量: 177.178
• InChiKey: IOXCNOLBLABFGH-UHFFFAOYSA-N

物化性质

• 沸点：
  347.7±37.0 °C(Predicted)
• 密度：
  1.321±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  32.9
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi

反应信息

• 作为反应物：
  描述：

  5-氟-3-甲基-1H-吲哚-2-甲醛 、 2-碘苯胺 在 potassium phosphate 、 copper(l) iodide 、 鹰爪豆碱 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 24.0h， 以78%的产率得到9-fluoro-7-methylindolo[1,2-a]quinoxaline
  参考文献：
  名称：

  Copper-Catalyzed Annulation of 2-Formylazoles with o-Aminoiodoarenes

  摘要：

  In the presence of catalytic CuI and sparteine, 2-formyl-pyrroles can be annulated with o-aminoiodoarenes to give Substituted pyrrolo[1,2-a]quinoxalines and related heterocycles. The reaction also works for annulation of 2-formylindoles, 2-formylimidazole, 2-formylbenzimidazole, and a 3-formylpyrazole.

  DOI：

  10.1021/jo9025644

文献信息

• Copper-Catalyzed Annulation of 2-Formylazoles with Aminoiodopyrazoles: Synthesis of New Heterocyclic Ring Systems
  作者：Jonathan T. Reeves、Zhulin Tan、Bruce Z. Lu、Chris H. Senanayake

  DOI：10.1002/jhet.1500

  日期：2013.5

  Various 2‐formylazoles underwent CuI/sparteine‐catalyzed annulation with 1‐substituted‐4‐iodo‐5‐aminopyrazoles to produce four new heterocyclic ring systems. The reaction was demonstrated for 2‐formylpyrroles, 2‐formylindoles, 2‐formylimidazole, and 3‐methyl‐5‐formylpyrazole. 3‐Substitution of the iodopyrazole was tolerated.

  各种2-甲酰基唑与1-取代-4-碘-5-氨基吡唑进行CuI /天冬氨酸催化的环化反应，制得四个新的杂环系统。证明了该反应涉及2-甲酰基吡咯，2-甲酰基吲哚，2-甲酰咪唑和3-甲基5-甲酰基吡唑。耐受碘代吡唑的3-取代。
• Synthesis of Diverse Heterocyclic Scaffolds by (3+3) and (3+4) Cycloannulations of Donor‐Acceptor Vinylcyclopropanes
  作者：Matteo Faltracco、Sebastian Strähler、Demi Snabilié、Eelco Ruijter

  DOI：10.1002/adsc.202101063

  日期：2022.1.4

  Palladium-catalyzed (3+3) and (3+4) cycloannulations between vinylcyclopropanes and various (hetero)aromatic aldehydes are reported. The use of phosphonate-substituted vinylcyclopropanes provides access to a variety of bi- or tricyclic heteroaromatic scaffolds via an allylation/olefination cascade. The nature of the mechanism was investigated by various control experiments.

  钯催化的 (3+3) 和 (3+4) 环化在乙烯基环丙烷和各种（杂）芳香醛之间形成。膦酸酯取代的乙烯基环丙烷的使用通过烯丙基化/烯化级联提供了获得各种双环或三环杂芳族支架的途径。通过各种控制实验研究了该机制的性质。
• Propylphosphonic anhydride (T3P®) catalyzed one-pot synthesis of α-aminonitriles
  作者：Sirigireddy Sudharsan Reddy、Bhoomireddy Rajendra Prasad Reddy、Peddiahgari Vasu Govardhana Reddy

  DOI：10.1016/j.cclet.2015.03.021

  日期：2015.6

  The Strecker reaction was performed via a one-pot three component condensation of hetero aromatic/aromatic aldehydes, secondary amines and trimetylsilyl cyanide in the presence of propylphosphonic anhydride (T3P®) to accomplish the corresponding α-aminonitriles. The main advantages of this method are very short reaction time and excellent yields.

  所述的Strecker反应，进行经由杂芳族/芳族醛，仲胺和trimetylsilyl氰化物在丙基膦酸酐（T3P的存在一锅三个组分缩合®）来完成相应的α氨基腈。该方法的主要优点是非常短的反应时间和优异的产率。
• NOVEL SUBSTITUTED OCTAHYDROCYCLOPENTA[C]PYRROL-4-AMINES AS CALCIUM CHANNEL BLOCKERS
  申请人：Searle Xenia B.

  公开号：US20110281870A1

  公开（公告）日：2011-11-17

  The present application relates to calcium channel inhibitors containing compounds of formula (I) wherein L 1 , L 2 , R 1 , R 2 , and R 3 are as defined in the specification. The present application also relates to compositions comprising such compounds, and methods of treating conditions and disorders using such compounds and compositions.

  本申请涉及含有式(I)化合物的钙通道抑制剂，其中L1，L2，R1，R2和R3如规范中所定义。本申请还涉及包含这种化合物的组合物和使用这种化合物和组合物治疗疾病和疾病的方法。
• [EN] NOVEL SUBSTITUTED OCTAHYDROCYCLOPENTA [C]PYRROL-4-AMINES AS CALCIUM CHANNEL BLOCKERS<br/>[FR] NOUVELLES OCTAHYDROCYCLOPENTA[C]PYRROL-4-AMINES SUBSTITUÉES COMME BLOQUEURS DE CANAUX CALCIQUES
  申请人：ABBOTT LAB

  公开号：WO2011149995A1

  公开（公告）日：2011-12-01

  The present application relates to calcium channel inhibitors containing compounds of formula (I) wherein L1, L2, R1, R2, and R3 are as defined in the specification. The present application also relates to compositions comprising such compounds, and methods of treating conditions and disorders using such compounds and compositions.