3-异丙基-2-甲基-1H-吲哚 | 31151-19-6

• 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
• 中文名称: 3-异丙基-2-甲基-1H-吲哚
• 英文名称: 3-isopropyl-2-methyl-1H-indole
• 英文别名: 2-methyl-3-propan-2-yl-1H-indole
• CAS: 31151-19-6
• 化学式: C₁₂H₁₅N
• mdl: MFCD11226298
• 分子量: 173.258
• InChiKey: WEDBVPQYBDSVSX-UHFFFAOYSA-N

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：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  3-异丙基-2-甲基-1H-吲哚 在 氧气 、 焦磷酸硫胺素 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 1-(2-Hydroperoxy-3-isopropylidene-2-methyl-2,3-dihydro-indol-1-yl)-ethanone
  参考文献：
  名称：

  Reactions of N-acylated indoles with singlet oxygen

  摘要：

  Reactions of seven N-acyl indole derivatives with singlet oxygen have been investigated. 1-Acetyl-(1a) and 1-(chloroacetyl)-2,3-dimethylindole (1b) gave exclusively 1-acetyl-(2a) and 1-(chloroacetyl)-2-hydroperoxy-3-methyleneindoline (2b), respectively, in high yields via ene reaction on irradiation with oxygen in the presence of TPP sensitizer. 1-Acetyl-3-methylindole (1c) gave only 1-acetyl-2-hydroperoxy-3-methyleneindoline (2c) in low yield under the same conditions. In contrast, 1-acetyl-2-methyl-3-ethylindole (3a) and 1-acetyl-2-methyl-3-isopropylindole (3b) gave a mixture of ene products, 2-hydroperoxy- and 3-hydroperoxyindolines (4a and b and 5a and b), in addition to 2,3-bond cleavage products 6a and 6b, respectively. In the case of 1-acetyl-2-methyl-3-tert-butylindole (7), only the product of 2,3-bond cleavage (8) was obtained. A 1,2-dioxetane is intermediate in the cleavage and could be observed after photooxygenation of 7 at -5-degrees-C by NMR and was reduced by trimethylphosphite and dimethyl sulfide. The decomposition rate constant of 1,2-dioxetane 10 was measured by NMR; E(a) is 24.6 kcal/mol.

  DOI：

  10.1021/jo00053a014
• 作为产物：
  描述：

  1-methyl-1-(2-methyl-1H-3-indolyl)ethyl (4-methylphenyl)sulfone 在 偶氮二异丁腈 、 三正丁基氢锡 、 sodium hydride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 9.0h， 生成 3-异丙基-2-甲基-1H-吲哚
  参考文献：
  名称：

  3-（1-芳基磺酰基烷基）吲哚与硝基烷烃的反应合成3-（2-硝基烷基）吲哚

  摘要：

  在碱性条件下，磺酰吲哚是乙烯基亚氨基亚氨基衍生物的有效前体，可与硝基烷反应，从而以高收率得到相应的硝基吲哚。该方法代表了吲哚向硝基烯烃的经典共轭加成的有效选择。

  DOI：

  10.1016/j.tetlet.2007.06.027

文献信息

• A Convenient Modification of the Fischer Indole Synthesis with a Solid Acid
  作者：Sosale Chandrasekhar、Somnath Mukherjee

  DOI：10.1080/00397911.2014.984854

  日期：2015.4.18

  the cation exchange resin Amberlite IR 120 in refluxing ethanol. A variety of enolizable aldehydes, and ketones and several substituted phenylhydrazines could thus be converted to the corresponding indoles in excellent yields (70–88%). Reaction times were typically 6–10 h, with the resin being then filtered off and the product isolated after minimal workup. GRAPHICAL ABSTRACT

  摘要 标题反应的新一锅版本包括在回流乙醇中加热羰基化合物、苯肼和阳离子交换树脂 Amberlite IR 120 的混合物。因此，各种可烯醇化的醛、酮和几种取代的苯肼可以以极好的收率（70-88%）转化为相应的吲哚。反应时间通常为 6-10 小时，然后将树脂过滤掉，并在最少的后处理后分离产物。图形概要
• Pyridobenzazepine compounds and methods for inhibiting mitotic progression
  申请人：Claiborne F. Christopher

  公开号：US20080045501A1

  公开（公告）日：2008-02-21

  This invention relates to compounds and methods for the treatment of cancer. In particular, the invention provides compounds that inhibit Aurora kinase, pharmaceutical compositions comprising the compounds, and methods of using the compounds for the treatment of cancer.

  这项发明涉及用于治疗癌症的化合物和方法。具体而言，该发明提供了抑制枢纽激酶的化合物，包括这些化合物的药物组合物，以及使用这些化合物治疗癌症的方法。
• Fischer Indole Synthesis in Brønsted Acidic Ionic Liquids: A Green, Mild, and Regiospecific Reaction System
  作者：Dan-Qian Xu、Wen-Long Yang、Shu-Ping Luo、Bing-Tao Wang、Jian Wu、Zhen-Yuan Xu

  DOI：10.1002/ejoc.200600886

  日期：2007.2

  A novel one-pot Fischer indole synthesis approach has been developed by using Bronsted acidic ionic liquids as dual solvent-catalysts. Yields of 83–97 % were obtained after reaction in BMImHSO4 at 70–110 °C in 0.5–6 h, and exclusive formation of 2,3-disubstituted indoles was observed in the reaction of alkyl methyl unsymmetrical ketones. The indoles produced could be conveniently separated from the

  通过使用布朗斯台德酸性离子液体作为双溶剂催化剂开发了一种新的单锅 Fischer 吲哚合成方法。在 BMImHSO4 中在 70–110 °C 下反应 0.5–6 小时后，产率为 83–97%，并且在烷基甲基不对称酮的反应中观察到了 2,3-二取代吲哚的独特形成。生成的吲哚可以方便地从反应混合物中分离出来，无需任何挥发性有机溶剂，而且 BMImHSO4 可以很容易地重复使用，只需 1 当量的简单处理后效率不会降低。HCl 中和，然后过滤。（© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007）
• HETEROBICYCLIC COMPOUNDS USEFUL AS KINASE INHIBITORS
  申请人：Dhar T.G. Murali

  公开号：US20080275052A1

  公开（公告）日：2008-11-06

  A compound of Formula (I) and enantiomers, diastereomers and pharmaceutically-acceptable salts thereof. Also disclosed are pharmaceutical compositions containing compounds of Formula I, and methods of treating conditions associated with the activity of p38 kinase.

  一种由化合物（I）及其对映体、非对映体异构体和药用可接受的盐组成的复合物。还公开了含有化合物（I）的药物组合物，以及治疗与p38激酶活性相关疾病的方法。
• Palladium-Catalyzed Amination/Dearomatization Reaction of Indoles and Benzofurans
  作者：Zhe Zhang、Bo-Sheng Zhang、Kai-Li Li、Yang An、Ce Liu、Xue-Ya Gou、Yong-Min Liang

  DOI：10.1021/acs.joc.0c00475

  日期：2020.6.19

  This report describes a palladium-catalyzed dearomatization and amination tandem reaction of 2,3-disubstituted indoles and benzofurans via the Catellani strategy. This reaction provides a new method for the construction of amino-substituted indoline-fused cyclic and benzofuran spiro compounds in good yields. The reaction has broad functional group compatibility and substrate scope.

  该报告描述了通过Catellani策略进行的钯催化的2,3-二取代的吲哚和苯并呋喃的脱芳香化和胺化串联反应。该反应提供了一种以高收率构建氨基取代的二氢吲哚稠合的环状和苯并呋喃螺环化合物的新方法。该反应具有广泛的官能团相容性和底物范围。