2-异丙基-1-甲基-1H-吲哚 | 65136-46-1

• 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: 2-异丙基-1-甲基-1H-吲哚
• 英文名称: 1-Methyl-2-isopropylindole
• 英文别名: 2-Isopropyl-1-methyl-1H-indole；1-methyl-2-propan-2-ylindole
• CAS: 65136-46-1
• 化学式: C₁₂H₁₅N
• mdl: MFCD00964058
• 分子量: 173.258
• InChiKey: QYUAUAYVRBCXJK-UHFFFAOYSA-N

物化性质

• 沸点：
  277.6±9.0 °C(Predicted)
• 密度：
  0.97±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2-异丙基-1-甲基-1H-吲哚 在 吡啶 、 三溴氧磷 作用下， 生成 (+)-tris[3-(2-isopropyl-1-methylindolyl)]phosphine oxide
  参考文献：
  名称：

  刚性立体元素缺失时的手性：构型稳定的C3对称螺旋桨的设计

  摘要：

  迄今为止，残余立体异构体是一种至今很少用于应用目的的立体异构体形式，尽管极为有趣，因为立体异构体的产生不涉及经典的刚性立体形成元素。在三叶片螺旋桨状分子中，与环的相关旋转有关的优选的立体异构化机制，可以使分离的异构体内部的立体异构体（残留的立体异构体）自由相互转化，从而可以通过更高的能量途径进行相互转化。考虑到作为立体选择过程中过渡金属的手性配体的未来应用前景，某些C 3合成了可能以残留对映体形式存在的对称磷中心螺旋桨，并探讨了将其外消旋物拆分为残留对映体的可能性。尽管三（芳基）甲烷在室温下构型稳定，但只有选定的三（芳基）膦氧化物显示出足够高的构型稳定性，以允许在室温下半制备水平上通过HPLC在手性固定相（CSP HPLC）上拆分。通过不同的技术（圆二色性（CD）信号衰减，动态CSP HPLC（CSP DHPLC），动态NMR分析（DNMR））评估稳定性，并对结果进行比较和讨论。磷的稳定性

  DOI：

  10.1002/chem.200801505
• 作为产物：
  描述：

  1-(1-Methyl-2-indolyl)-1-methylethanol 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 15.0h， 以59%的产率得到2-异丙基-1-甲基-1H-吲哚
  参考文献：
  名称：

  Abbreviated Ibogaine Congeners. Synthesis and Reactions of Tropan-3-yl-2- and -3-indoles. Investigation of an Unusual Isomerization of 2-Substituted Indoles Using Computational and Spectroscopic Techniques

  摘要：

  The syntheses of several N-methyltropan-3-ylindoles, designed as congeners of ibogaine, are described. The synthetic approach to N-methyltropan-3-yl-2-indole revealed that the tropanyl 3'-center was quite sensitive to acid-catalyzed epimerization. The carbocyclic analog, N-methyl-2-[bicyclo[3.2.1]-oct-3-anyl] indole, also underwent this rearrangement. However, N-methyltropan-3-yl-3-indole was insensitive to acid or base, even under more vigorous conditions. This simple isomerization is quite rare for 2-substituted indoles, especially for cases where the center of reaction is not additionally activated, and normally only takes place under extreme reaction conditions. The mechanism of this reaction was investigated using ab initio molecular orbital calculations, NMR spectroscopy and deuterium labeling studies. These results indicate that, in contrast to those previously obtained for more reactive 2-substituted indoles, the reaction can best be explained using a simple exchange mechanism involving the exocyclic enamine tautomer of the indole ring as an intermediate. The difference in reactivity is suggested to arise from a decrease in the relative energy of the exocyclic enamine tautomer due to the presence of increased strain in the endo bicyclic 2-substituent. The title compounds displayed modest pharmacological activity in a variety of biological assays.

  DOI：

  10.1021/jo00087a037

文献信息

• SUBSTITUTED 4-AMINOCYCLOHEXANE DERIVATIVES
  申请人：NOLTE Bert

  公开号：US20090247530A1

  公开（公告）日：2009-10-01

  The invention relates to compounds that have an affinity to the μ-opioid receptor and the ORL 1-receptor, methods for their production, medications containing these compounds and the use of these compounds for the treatment of pain and other conditions.

  这项发明涉及具有与μ-阿片受体和ORL 1-受体亲和力的化合物，其生产方法，含有这些化合物的药物以及利用这些化合物治疗疼痛和其他疾病的用途。
• ACTIVATORS OF THE RETINOIC ACID INDUCIBLE GENE "RIG-I" PATHWAY AND METHODS OF USE THEREOF
  申请人：Kineta Immuno-Oncology LLC

  公开号：US20200055871A1

  公开（公告）日：2020-02-20

  The present invention is directed to compounds of Formula (I), which are activators of the RIG-I pathway.

  本发明涉及式（I）化合物，该化合物是RIG-I通路的激活剂。
• [EN] STING AGONISTS AND USES THEREOF<br/>[FR] AGONISTES DE STING ET LEURS UTILISATIONS
  申请人：NIMBUS TITAN INC

  公开号：WO2020132582A1

  公开（公告）日：2020-06-25

  The present invention provides compounds, compositions thereof, and methods of using the same for the modulation of STING, and the treatment of STING-mediated disorders.

  本发明提供了化合物、其组合物以及使用这些化合物调节STING并治疗STING介导的疾病的方法。
• [EN] METHODS AND INTERMEDIATES FOR THE PREPARATION OF MACROLACTAMS<br/>[FR] PROCÉDÉS ET INTERMÉDIAIRES POUR LA PRÉPARATION DE MACROLACTAMES
  申请人：MERCK SHARP & DOHME

  公开号：WO2015095430A1

  公开（公告）日：2015-06-25

  The present invention relates to synthetic processes useful in the preparation of macrolactams that inhibit hepatitis C virus (HCV), specifically macrolactam compounds that inhibit the HCV NS3 protease activity and have application in the treatment of conditions caused by HCV. The present invention also encompasses intermediates useful in the disclosed synthetic processes and the methods of their preparation.

  本发明涉及在制备抑制丙型肝炎病毒（HCV）的大环内酰胺类化合物中有用的合成工艺，特别是抑制HCV NS3蛋白酶活性并可用于治疗由HCV引起的病症的大环内酰胺化合物。本发明还包括在所述合成工艺中有用的中间体及其制备方法。
• [EN] COMPOSITIONS FOR PROMOTING READTHROUGH OF PREMATURE TERMINATION CODONS, AND METHODS OF USING THE SAME<br/>[FR] COMPOSITIONS PERMETTANT DE FAVORISER LA TRANSLECTURE DE CODONS DE TERMINAISON PRÉMATURÉE, ET LEURS PROCÉDÉS D'UTILISATION
  申请人：THE CENTRE FOR DRUG RES AND DEV

  公开号：WO2017049409A1

  公开（公告）日：2017-03-30

  Disclosed are compounds of general formula (I) that promote readthrough of a premature termination codon (PTC) of an RNA molecule in a translation system, and their use, alone or in combination with other compounds, such as aminoglycoside, to treat diseases or disorders ameliorated by modulation of a premature termination codon (PTC) of an RNA molecule in a translation system. The disorder or disease may be Dystrophic epidermolysis bullosa, Batten disease, Duchenne muscular dystrophy, cancer, and spinal muscular atrophy. Ar-L-B (I)

  公开了通式(I)的化合物，它们能够促进RNA分子在翻译系统中过早终止密码子(PTC)的通读，以及它们单独或与其他化合物如氨基糖苷的组合使用，用于治疗通过调节翻译系统中RNA分子的过早终止密码子(PTC)而得到改善的疾病或失调。该疾病或失调可能是营养不良性表皮松解症、贝敦病、杜氏肌营养不良症、癌症和脊髓性肌萎缩症。Ar-L-B (I)