2-(1-methyl-1H-indol-3-yl)propanenitrile | 176688-64-5

• 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: 2-(1-methyl-1H-indol-3-yl)propanenitrile
• 英文别名: 2-(1-methylindol-3-yl)propanenitrile
• CAS: 176688-64-5
• 化学式: C₁₂H₁₂N₂
• 分子量: 184.241
• InChiKey: JKHJNKXEFNBGAR-UHFFFAOYSA-N

物化性质

• 沸点：
  349.5±17.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  28.7
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(1-methyl-1H-indol-3-yl)propanenitrile 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以63%的产率得到2-(1-Methylindol-3-yl)propan-1-amine
  参考文献：
  名称：

  New indole derivatives as ACAT inhibitors: synthesis and structure-activity relationships

  摘要：

  A series of ureas containing the indole group were synthesized and assessed for their ability to inhibit arterial and intestinal ACAT and to lower plasma total cholesterol in a cholesterol-fed rat model. The structural modulations carried out in this series led to compounds which proved to be very active in both the inhibition of aortic ACAT in vitro and the inhibition of rat cholesterol intestinal absorption in vivo. Several compounds from this series exhibit a remarkable hypocholesterolaemic effect with ED(25) less than 0.1 mg/kg po.

  DOI：

  10.1016/0223-5234(96)80445-4
• 作为产物：
  描述：

  吲哚-3-乙腈 在 sodium hydroxide 、 苄基三甲基氢氧化铵 、 sodium hydride 作用下， 以 甲醇 为溶剂， 反应 10.0h， 生成 2-(1-methyl-1H-indol-3-yl)propanenitrile
  参考文献：
  名称：

  New indole derivatives as ACAT inhibitors: synthesis and structure-activity relationships

  摘要：

  A series of ureas containing the indole group were synthesized and assessed for their ability to inhibit arterial and intestinal ACAT and to lower plasma total cholesterol in a cholesterol-fed rat model. The structural modulations carried out in this series led to compounds which proved to be very active in both the inhibition of aortic ACAT in vitro and the inhibition of rat cholesterol intestinal absorption in vivo. Several compounds from this series exhibit a remarkable hypocholesterolaemic effect with ED(25) less than 0.1 mg/kg po.

  DOI：

  10.1016/0223-5234(96)80445-4

文献信息

• Selective α‐Monomethylation by an Amine‐Borane/ <i>N</i> , <i>N</i> ‐Dimethylformamide System as the Methyl Source
  作者：Hui‐Min Xia、Feng‐Lian Zhang、Tian Ye、Yi‐Feng Wang

  DOI：10.1002/anie.201804794

  日期：2018.9.3

  A new and practical α‐monomethylation strategy using an amine‐borane/N,N‐dimethylformamide (R3N‐BH3/DMF) system as the methyl source was developed. This protocol has been found to be effective in the α‐monomethylation of arylacetonitriles and arylacetamides. Mechanistic studies revealed that the formyl group of DMF delivered the carbon and one hydrogen atoms of the methyl group, and R3N‐BH3 donated

  开发了一种新的实用的α-单甲基化策略，该方法使用胺-硼烷/ N，N-二甲基甲酰胺（R 3 N-BH 3 / DMF）系统作为甲基来源。已发现该方案对芳基乙腈和芳基乙酰胺的α-单甲基化有效。机理研究表明，DMF的甲酰基传递了碳原子和甲基的一个氢原子，而R 3 N-BH 3则贡献了其余的两个氢原子。如此独特的反应路径使得使用Me 2 NH-BH 3 / d可控制地组装CDH 2，CD 2 H和CD 3单元。7 ‐ DMF ，Me 3 N‐BD 3 / DMF和Me 3 N‐BD 3 / d 7 ‐ DMF系统。证实了该方法在抗炎药氟比洛芬及其各种氘标记衍生物的简便合成中的进一步应用。
• Catalytic C(sp²)–C(sp³) Bond Formation of Methoxyarenes by the Organic Superbase <i>t</i>-Bu-P4
  作者：Masanori Shigeno、Kazutoshi Hayashi、Kanako Nozawa-Kumada、Yoshinori Kondo

  DOI：10.1021/acs.orglett.0c03507

  日期：2020.11.20

  [cyano, nitro, (non)enolizable ketone, chloride, and amide moieties] are allowed on methoxyarenes. Moreover, an array of alkanenitriles with/without an aryl moiety at the nitrile α-position can be employed. The system also features no requirement of a stoichiometric base, MeOH (not salt waste) formation as a byproduct, and the production of congested quaternary carbon centers.

  有机超碱催化剂t -Bu-P4实现了烷烃前亲核体对甲氧基芳烃的亲核芳族取代。在甲氧基芳烃上可以使用各种官能团[氰基，硝基，（不可）烯化的酮，氯和酰胺部分）。此外，可以使用在腈α-位具有/不具有芳基部分的链烷腈的阵列。该系统还不需要化学计量的碱，不需要的副产物MeOH（无盐废料）形成以及拥挤的季碳中心的生产。
• A Practical Method for <i>N</i>-Methylation of Indoles Using Dimethyl Carbonate
  作者：Xinglong Jiang、Ashish Tiwari、Maethonia Thompson、Zhihong Chen、Thomas P. Cleary、Thomas B. K. Lee

  DOI：10.1021/op0102215

  日期：2001.11.1

  A new method for N-methylation of indoles using environmentally safe and less toxic methylating reagent, dimethyl carbonate (DMC), has been developed. The effect of various functional groups on the indole ring has been investigated. This method provides the desired product in high yields with high purity and is suitable for large-scale production. This process was used successfully in a 300-gal reactor

  已开发出一种使用环境安全且毒性较小的甲基化试剂碳酸二甲酯 (DMC) 对吲哚进行 N-甲基化的新方法。已经研究了各种官能团对吲哚环的影响。该方法以高收率和高纯度提供所需产物，适合大规模生产。该工艺成功地用于 300 加仑反应器系列中，用于 6-硝基吲哚的 N-甲基化。
• Defluorinative Transformation of (2,2,2-Trifluoroethyl)arenes Catalyzed by the Phosphazene Base <i>t</i>-Bu-P2
  作者：Masanori Shigeno、Yoshiteru Shishido、Amane Soga、Kanako Nozawa-Kumada、Yoshinori Kondo

  DOI：10.1021/acs.joc.2c02034

  日期：2023.2.3

  In this study, we demonstrated that 1-tert-butyl-2,2,4,4,4-pentakis(dimethylamino)-2λ5,4λ5-catenadi(phosphazene) (t-Bu-P2) catalyzes the defluorinative functionalization reactions of (2,2,2-trifluoroethyl)arenes with alkanenitriles to produce monofluoroalkene products. The reaction proceeds through HF elimination from a (2,2,2-trifluoroethyl)arene to form a gem-difluorostyrene intermediate, which is

  在这项研究中，我们证明了 1- tert -butyl-2,2,4,4,4-pentakis(dimethylamino)-2λ5,4λ5-catenadi(phosphazene) ( t -Bu -P2) 催化 ( 2,2,2-三氟乙基)芳烃与烷腈生成单氟烯烃产品。该反应通过从 (2,2,2-三氟乙基) 芳烃中消除 HF 以形成偕二氟苯乙烯中间体，然后进行链烷腈的亲核加成和氟化物阴离子的消除。该催化与多种官能团相容。
• α-Methylation of 2-Arylacetonitrile by a Trimethylamine-Borane/CO₂ System
  作者：Xiaowei Zhang、Sheng Wang、Chanjuan Xi

  DOI：10.1021/acs.joc.9b01587

  日期：2019.8.2

  A highly selective monomethylation of 2-arylacetonitrile using CO2 is described. The utilization of trimethylamine-borane facilitates the six-electron reduction of CO2. This reaction is the first selective six-electron reductive functionalization of CO2 faciliated by C(sp(3))-H bonds. A variety of 2-arylpropionitrile was obtained in good yields. The reaction could also be applied at the gram scale.