3-甲酰基-7-氰基-1H-吲哚 | 467451-63-4

• 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
• 中文名称: 3-甲酰基-7-氰基-1H-吲哚
• 英文名称: 3-formyl-7-cyano-1H-indole
• 英文别名: 7-cyano-1H-indole-3-carbaldehyde；3-formyl-1H-indole-7-carbonitrile
• CAS: 467451-63-4
• 化学式: C₁₀H₆N₂O
• mdl: MFCD11110373
• 分子量: 170.17
• InChiKey: WFXZKENGRJYLOG-UHFFFAOYSA-N

物化性质

• 沸点：
  429.6±25.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56.6
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  2-8°C，储存时建议使用惰性气体。

反应信息

• 作为反应物：
  描述：

  3-甲酰基-7-氰基-1H-吲哚 在 lithium aluminium tetrahydride 、 palladium diacetate 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 生成 trans-2-[7-cyano-1-(4-toluenesulfonyl)-1H-indol-3-yl]cyclopropanecarboxaldehyde
  参考文献：
  名称：

  Conformationally Restricted Homotryptamines. 2. Indole Cyclopropylmethylamines as Selective Serotonin Reuptake Inhibitors

  摘要：

  A series of indole cyclopropylmethylamines were found to be potent serotonin reuptake inhibitors. Nitrile substituents at the 5 and 7 positions of the indole ring gave high affinity for hSERT, and the preferred cyclopropane stereochemistry was determined to be (1S,2S)-trans. The cis-cyclopropanes had 20- to 30-fold less affinity than the trans, and the preferred cis stereochemistry was (1R,2S)-cis. Substitution of the indole N-1 position with methyl or ethyl groups gave a 10- to 30-fold decrease in affinity for hSERT, suggesting either a hydrogen-bonding interaction or limited steric tolerance in the region of the indole nitrogen. Compound (+)-12a demonstrated potent hSERT binding (K-i = 0.18 nM) in vitro and was more than 1000-fold less potent at hDAT, hNET, 5-HT1A, and 5-HT6. In vivo, (+)-12a produced robust, dose-dependent increases in extracellular serotonin in rat frontal cortex typical of a selective serotonin reuptake inhibitor. The maximal response produced by (+)-12a was similar to that of fluoxetine but at an approximately 10-fold lower dose.

  DOI：

  10.1021/jm0503291
• 作为产物：
  描述：

  7-氰基吲哚 、 N,N-二甲基甲酰胺 在 草酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以70%的产率得到3-甲酰基-7-氰基-1H-吲哚
  参考文献：
  名称：

  [EN] COMPOUNDS
  [FR] COMPOSÉS

  摘要：

  本发明涉及具有药理活性的新型噁二唑衍生物，其制备方法，含有它们的药物组合物以及它们在治疗各种疾病中的应用。

  公开号：

  WO2009153307A1

文献信息

• COMPOUNDS
  申请人：Castro Pineiro Jose Luis

  公开号：US20100029729A1

  公开（公告）日：2010-02-04

  The present invention relates to novel oxadiazole derivatives having pharmacological activity, processes for their preparation, pharmaceutical compositions containing them and their use in the treatment of various disorders.

  本发明涉及具有药理活性的新型噁二唑衍生物，其制备方法，含有它们的药物组合物以及它们在治疗各种疾病中的应用。
• N-(2-arylethyl) benzylamines as antagonists of the 5-ht6 receptor
  申请人：Chen Zhaogen

  公开号：US20060009511A9

  公开（公告）日：2006-01-12

  The present invention provides compounds of formula (I), which are antagonists of the 5-HT 6 receptor.

  本发明提供了式(I)的化合物，它们是5-HT6受体的拮抗剂。
• N-(2-ARYLETHYL)BENZYLAMINES AS ANTAGONISTS OF THE 5-HT6 RECEPTOR
  申请人：Chen Zhaogen

  公开号：US20070099909A1

  公开（公告）日：2007-05-03

  The present invention provides compounds of formula (I), which are antagonists of the 5-HT 6 receptor.

  本发明提供了公式（I）的化合物，它们是5-HT6受体的拮抗剂。
• 1,2,4-oxadiazole indole compounds
  申请人：Glaxo Group Limited

  公开号：US08217028B2

  公开（公告）日：2012-07-10

  The present invention relates to novel oxadiazole derivatives having pharmacological activity, processes for their preparation, pharmaceutical compositions containing them and their use in the treatment of various disorders.

  本发明涉及具有药理活性的新型噁唑烷衍生物，其制备过程，包含它们的制药组合物以及它们在治疗各种疾病中的使用。
• A stable and recyclable Z-scheme g-C₃N₄/rGO/BiVO₄ heterojunction photocatalyst for site-selective C-3 formylation of indoles with methanol as a formyl source under visible light
  作者：Zhenkai Lei、Fei Xue、Bin Wang、Shijie Wang、Yonghong Zhang、Yu Xia、Weiwei Jin、Chenjiang Liu

  DOI：10.1039/d2gc03858g

  日期：——

  A stable and recyclable Z-scheme g-C3N4/rGO/BiVO4 heterojunction photocatalyst was constructed by a facile two-step hydrothermal procedure. The photocatalyst was used for the synthesis of C-3 formylated indoles from indoles with methanol as an atom-economical formyl source for the first time, and 30% g-C3N4/rGO/BiVO4 exhibited superior photocatalytic efficiency. Quenching experiments showed that the

  通过简便的两步水热法构建了一种稳定且可回收的 Z 型 gC 3 N 4 /rGO/BiVO 4异质结光催化剂。该光催化剂首次以甲醇为原子经济型甲酰源，以30% gC 3 N 4 / rGO/BiVO 4为原料，以吲哚为原料合成C-3甲酰化吲哚。表现出优异的光催化效率。猝灭实验表明，光生电子和空穴是实现反应的主要光活性物质。这种甲酰化反应具有优异的官能团耐受性、可重复使用的光催化剂和温和的反应条件等优点。克级合成表明了该策略在实际应用中的未来前景。