1,5-dimethyl-1H-indole-3-carboxylic acid | 1260831-20-6

• 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: 1,5-dimethyl-1H-indole-3-carboxylic acid
• 英文别名: 1,5-Dimethylindole-3-carboxylic acid；1,5-dimethylindole-3-carboxylic acid
• CAS: 1260831-20-6
• 化学式: C₁₁H₁₁NO₂
• 分子量: 189.214
• InChiKey: LWQYYRFASDNRGT-UHFFFAOYSA-N

物化性质

• 沸点：
  401.6±25.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  42.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,5-dimethyl-1H-indole-3-carboxylic acid 在 吡啶 、 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 生成 N-methoxy-1,5-dimethyl-1H-indole-3-carboxamide
  参考文献：
  名称：

  Construction of indoloquinolinones via Pd(II)-catalyzed tandem C C/C N bond formation: application to the total synthesis of isocryptolepine

  摘要：

  DOI：

  10.1016/j.tetlet.2014.11.008
• 作为产物：
  描述：

  5-甲基吲哚-3-甲酸甲酯 在 甲醇 、 potassium carbonate 、 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 1,5-dimethyl-1H-indole-3-carboxylic acid
  参考文献：
  名称：

  Construction of indoloquinolinones via Pd(II)-catalyzed tandem C C/C N bond formation: application to the total synthesis of isocryptolepine

  摘要：

  DOI：

  10.1016/j.tetlet.2014.11.008

文献信息

• Enantioselective Three-Component Fluoroalkylarylation of Unactivated Olefins through Nickel-Catalyzed Cross-Electrophile Coupling
  作者：Hai-Yong Tu、Fang Wang、Liping Huo、Yuanbo Li、Shengqing Zhu、Xian Zhao、Huan Li、Feng-Ling Qing、Lingling Chu

  DOI：10.1021/jacs.0c03708

  日期：2020.5.27

  A nickel-catalyzed, enantioselective, three-component fluoroalkylarylation of unactivated alkenes with aryl halides and perfluoroalkyl iodides has been described. This cross-electrophile coupling protocol utilizes a chiral nickel/BiOx system as well as a pendant chelating group to facilitate the challenging three-component, asymmetric difunctionalization of unactivated alkenes, providing direct access

  镍催化、对映选择性、三组分氟烷基芳基化未活化的烯烃与芳基卤化物和全氟烷基碘化物已被描述。这种交叉亲电偶联方案利用手性镍/BiOx 系统以及悬垂的螯合基团来促进未活化烯烃的具有挑战性的三组分不对称双官能化，从而以高效和出色的对映选择性直接获得有价值的手性 β-氟烷基芳基烷烃. 温和的条件允许广泛的底物范围以及良好的官能团耐受性。
• Salicylaldehyde-Promoted Cobalt-Catalyzed C–H/N–H Annulation of Indolyl Amides with Alkynes: Direct Synthesis of a 5-HT3 Receptor Antagonist Analogue
  作者：Mao-Gui Huang、Shuai Shi、Ming Li、Yue-Jin Liu、Ming-Hua Zeng

  DOI：10.1021/acs.orglett.1c02502

  日期：2021.9.17

  A cobalt-catalyzed annulation of the C(sp2)–H/N–H bond of indoloamides with alkynes assisted by 8-aminoquinoline is reported for the synthesis of six-membered indololactams. The use of salicylaldehyde as the ligand is crucial for this transformation. The protocol has a broad scope for both alkynes and indoles. Preparing an active Co complex illustrates that salicylaldehyde plays a key role in the C–H

  据报道，在 8-氨基喹啉的辅助下，吲哚酰胺的 C(sp 2 )-H/N-H 键与炔烃的钴催化环化可用于合成六元吲哚内酰胺。使用水杨醛作为配体对于这种转化至关重要。该协议对炔烃和吲哚都有广泛的适用范围。制备活性 Co 复合物说明水杨醛在 C-H 活化步骤中起关键作用。合成应用通过多环 5-HT3 受体拮抗剂的克级反应和一步构建得到证实。
• [EN] α7 NICOTINIC ACETYLCHOLINE RECEPTOR MODULATORS AND USES THEREOF - III<br/>[FR] MODULATEURS DU RÉCEPTEUR NICOTINIQUE α7 DE L'ACÉTYLCHOLINE ET UTILISATIONS DE CEUX-CI - III
  申请人：BIONOMICS LTD

  公开号：WO2014172759A1

  公开（公告）日：2014-10-30

  The present invention relates to chemical compounds useful in the positive modulation of the alpha 7 nicotinic acetylcholine receptor (α7 nAChR).

  本发明涉及对α7尼古丁乙酰胆碱受体（α7 nAChR）进行正向调节的化合物。
• ARYL CARBOXAMIDE DERIVATIVES AS TTX-S BLOCKERS
  申请人：Yamagishi Tatsuya

  公开号：US20120232052A1

  公开（公告）日：2012-09-13

  The present invention relates to aryl carboxamide derivatives of formula (I), wherein Ar 1 is phenyl; Ar 2 is aryl; n is 1-4; X is —O—, —S—, —SO— or —SO 2 —, a prodrug thereof or a pharmaceutically acceptable salt thereof, which have blocking activities of voltage gated sodium channels as the TTX-S channels, and which are useful in the treatment or prevention of such disorders and diseases as pain in which voltage gated sodium channels are involved. The invention also relates to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases as pain in which voltage gated sodium channels are involved.

  本发明涉及公式（I）的芳基羧酰胺衍生物，其中Ar1是苯基；Ar2是芳基；n为1-4；X为—O—、—S—、—SO—或—SO2—，其前体药物或其药学上可接受的盐，具有阻断电压门控钠通道如TTX-S通道的活性，并在治疗或预防涉及电压门控钠通道的疾病和疾病，如疼痛方面中有用。本发明还涉及包含这些化合物的制药组合物以及这些化合物和组合物在预防或治疗涉及电压门控钠通道的疾病和疾病，如疼痛方面的使用。
• ARYL SUBSTITUTED CARBOXAMIDE DERIVATIVES AS CALCIUM OR SODIUM CHANNEL BLOCKERS
  申请人：RaQualia Pharma Inc.

  公开号：US20150322052A1

  公开（公告）日：2015-11-12

  The present invention relates to aryl substituted carboxamide derivatives of formula (I) or a pharmaceutically acceptable salt thereof, which have blocking activities of T-type calcium channels or voltage gated sodium channels as the tetrodotoxin-sensitive (TTX-S) blocker such as Na V1.3 and Na V1.7 , and which are useful in the treatment or prevention of disorders and diseases in which T-type calcium channels or voltage gated sodium channels are involved. The invention also relates to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which T-type calcium channels or voltage gated sodium channels are involved.

  本发明涉及式（I）的芳基取代羧酰胺衍生物或其药学上可接受的盐，其具有T型钙通道或电压门控钠通道的阻滞活性，如NaV1.3和NaV1.7，可用于治疗或预防涉及T型钙通道或电压门控钠通道的疾病和疾病。本发明还涉及包含这些化合物的制药组合物以及在预防或治疗涉及T型钙通道或电压门控钠通道的疾病中使用这些化合物和组合物。