1-(1-甲基-2-苯基吲哚-3-基)乙酮 | 62367-64-0

• 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: 1-(1-甲基-2-苯基吲哚-3-基)乙酮
• 英文名称: 1-(1-methyl-2-phenyl-1H-indol-3-yl)ethan-1-one
• 英文别名: 1-(1-methyl-2-phenyl-1H-indol-3-yl)ethanone；3-acetyl-1-methyl-2-phenylindole；N-methyl-3-acetyl-2-phenylindole；1-(1-methyl-2-phenyl-indol-3-yl)-ethanone；1-(1-Methyl-2-phenyl-indol-3-yl)-aethanon；1-Methyl-2-phenyl-3-acetylindol；Ethanone, 1-(1-methyl-2-phenyl-1H-indol-3-yl)-；1-(1-methyl-2-phenylindol-3-yl)ethanone
• CAS: 62367-64-0
• 化学式: C₁₇H₁₅NO
• mdl: MFCD12633113
• 分子量: 249.312
• InChiKey: IKIQUACDGVADHX-UHFFFAOYSA-N

物化性质

• 熔点：
  66-68 °C
• 沸点：
  448.3±33.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.117
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(1-甲基-2-苯基吲哚-3-基)乙酮 在 盐酸 作用下， 生成 1-甲基-2-苯基吲哚
  参考文献：
  名称：

  Kohlrausch, Justus Liebigs Annalen der Chemie, 1889, vol. 253, p. 23

  摘要：

  DOI：
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 zinc(II) chloride 作用下， 生成 1-(1-甲基-2-苯基吲哚-3-基)乙酮
  参考文献：
  名称：

  Kohlrausch, Justus Liebigs Annalen der Chemie, 1889, vol. 253, p. 23

  摘要：

  DOI：

文献信息

• Iminyl-radicals by electrochemical decarboxylation of α-imino-oxy acids: construction of indole-fused polycyclics
  作者：Jin-Lin Wan、Jian-Feng Cui、Wei-Qiang Zhong、Jing-Mei Huang

  DOI：10.1039/d1cc03891e

  日期：——

  Iminyl radicals are reactive intermediates that can be used for the construction of various valuable heterocycles. Herein, the electrochemical decarboxylation of α-imino-oxy acids for the generation of iminyl radicals has been accomplished under exogenous-oxidant- and metal-free conditions through the use of nBu4NBr as a mediator. The resulting iminyl radicals undergo intramolecular cyclization smoothly

  亚胺基是反应性中间体，可用于构建各种有价值的杂环。在此，通过使用n Bu 4 NBr 作为介体，在无外源氧化剂和无金属条件下完成了用于产生亚胺基自由基的 α-亚氨基-羟基酸的电化学脱羧。所得亚胺基自由基与相邻的（杂）芳烃顺利进行分子内环化，得到一系列吲哚稠合的多环化合物。
• Palladium-catalyzed regioselective C–H fluoroalkylation of indoles at the C4-position
  作者：Arun Jyoti Borah、Zhuangzhi Shi

  DOI：10.1039/c7cc01274h

  日期：——

  An exclusive catalytic C4-selective fluoroalkylation of indoles with highly active (1H, 1H-perfluoroalkyl)mesityliodonium triflate has been described.

  已经描述了具有高活性（1 H，1 H-全氟烷基）间苯二甲磺酸三氟甲磺酸酯的吲哚的排他性催化C 4-选择性氟代烷基化。
• Electrophilic ipso-substitutions. Part 1. Reaction of 3-substituted indoles with nitronium and nitrosonium ions
  作者：Martino Colonna、Lucedio Greci、Marino Poloni

  DOI：10.1039/p29810000628

  日期：——

  3-Substituted indoles react with nitronium and nitrosonium ions to yield 3-nitroindole. In both cases the reaction was interpreted as an electrophilic ipso-substitution. The reaction mechanism is interpreted by hypothesizing the formation of a σ-complex-like intermediate, which is some cases is preceded by an electron-transfer process. An order for the leaving abilities of the different electrofugal

  3-取代的吲哚与硝鎓和硝鎓离子反应，生成3-硝基吲哚。在两种情况下，该反应均被解释为亲电的ipso取代。通过假设形成类似σ络合物的中间体来解释反应机理，在某些情况下会先发生电子转移过程。讨论了不同电真菌基团的离去能力的顺序。
• Ruthenium-catalyzed annulation of alkynes with amides via formyl translocation
  作者：Cui-Yan Wu、Ming Hu、Yu Liu、Ren-Jie Song、Yong Lei、Bo-Xiao Tang、Rong-Jiang Li、Jin-Heng Li

  DOI：10.1039/c2cc17887g

  日期：——

  The first example of Ru-catalyzed intramolecular annulation of alkynes with amidesviaformyl translocation has been developed, which provides an efficient approach for the synthesis of 1H-indole-3-carbaldehydes.

  第一个钌催化的炔烃与酰胺通过甲酰基易位发生分子内成环的例子已经开发出来，这为合成 1H-吲哚-3-甲醛提供了一种有效的方法。
• Indole derivatives
  申请人：Glaxo Group Limited

  公开号：US04814344A1

  公开（公告）日：1989-03-21

  The invention relates to compounds of formula (I) ##STR1## wherein R.sup.1 represents a hydrogen atom or a group selected from C.sub.1-10 alkyl, C.sub.3-6 alkenyl, C.sub.3-10 alkynyl, C.sub.3-7 cycloalkyl, C.sub.3-7 cycloalkyl C.sub.1-4 alkyl, phenyl, or phenyl C.sub.1-3 alkyl, --CO.sub.2 R.sup.10, --COR.sup.10, --CONR.sup.10 R.sup.11 or --SO.sub.2 R.sup.10 (wherein R.sup.10 and R.sup.11, which may be the same or different, each represents a hydrogen atom, a C.sub.1-6 alkyl or C.sub.3-7 cycloalkyl group, or a phenyl or phenylC.sub.1-4 alkyl group, in which the phenyl group is optionally substituted by one or more C.sub.1-4 alkyl, C.sub.1-4 alkoxy or hydroxy groups or halogen atoms, with the proviso that R.sup.10 does not represent a hydrogen atom when R.sup.1 represents a group --CO.sub.2 R.sup.10 or --SO.sub.2 R.sup.10); R.sub.2 represents a hydrogen atom or a C.sub.1-6 alkyl, C.sub.3-6 alkenyl, C.sub.3-7 cycloalkyl, phenyl or phenyl C.sub.1-3 alkyl group; R.sub.3 and R.sub.4, which may be the same or different, each represents a hydrogen atom or a C.sub.1-6 alkyl group; One of the groups represented by R.sup.5, R.sup.6 and R.sup.7 is a hydrogen atom or a C.sub.1-6 alkyl, C.sub.1-6 hydroxyalkyl, C.sub.3-7 cycloalkyl, C.sub.2-6 alkenyl, phenyl or phenyl C.sub.1-3 alkyl group, and each of the other two groups, which may be the same or different, represents a hydrogen atom or a C.sub.1-6 alkyl group; and Q represents a hydrogen or a halogen atom, or a hydroxy, C.sub.1-4 alkoxy, phenyl C.sub.1-3 alkoxy or C.sub.1-6 alkyl group or a group --NR.sup.8 R.sup.9 or --CONR.sup.8 R.sup.9 wherein R.sup.8 and R.sup.9, which may be the same or different, each represents a hydrogen atom or a C.sub.1-4 alkyl or C.sub.3-4 alkenyl group, or together with the nitrogen atom to which they are attached form a saturated 5 to 7 membered ring; and physiologically acceptable salts and solvates thereof. The comopounds are potent and selective antagonists of the effect of 5-HT at 5-HT.sub.3 receptors and are useful, for example, in the treatment of psychotic disorders, anxiety, and nausea and vomiting.

  本发明涉及化合物的公式（I）## STR1 ## 其中R.sup.1代表氢原子或从C.sub.1-10烷基，C.sub.3-6烯基，C.sub.3-10炔基，C.sub.3-7环烷基，C.sub.3-7环烷基C.sub.1-4烷基，苯基或苯基C.sub.1-3烷基，--CO.sub.2R.sup.10，--COR.sup.10，--CONR.sup.10R.sup.11或--SO.sub.2R.sup.10（其中R.sup.10和R.sup.11，可以相同或不同，每个代表氢原子，C.sub.1-6烷基或C.sub.3-7环烷基，或苯基或苯基C.sub.1-4烷基，其中苯基可以选择性地被一个或多个C.sub.1-4烷基，C.sub.1-4烷氧基或羟基或卤素原子取代，但有条件的是当R.sup.1代表--CO.sub.2R.sup.10或--SO.sub.2R.sup.10时，R.sup.10不代表氢原子）;R.sub.2代表氢原子或C.sub.1-6烷基，C.sub.3-6烯基，C.sub.3-7环烷基，苯基或苯基C.sub.1-3烷基;R.sub.3和R.sub.4，可以相同或不同，每个代表氢原子或C.sub.1-6烷基;由R.sup.5，R.sup.6和R.sup.7代表的群中的一个是氢原子或C.sub.1-6烷基，C.sub.1-6羟基烷基，C.sub.3-7环烷基，C.sub.2-6烯基，苯基或苯基C.sub.1-3烷基，而其他两个群，可以相同或不同，代表氢原子或C.sub.1-6烷基; Q代表氢或卤素原子，或羟基，C.sub.1-4烷氧基，苯基C.sub.1-3烷氧基或C.sub.1-6烷基，或--NR.sup.8R.sup.9或--CONR.sup.8R.sup.9群，其中R.sup.8和R.sup.9，可以相同或不同，每个代表氢原子或C.sub.1-4烷基或C.sub.3-4烯基，或与它们连接的氮原子一起形成饱和的5至7元环；以及其生理上可接受的盐和溶剂。这些化合物是5-HT.sub.3受体效应的有效和选择性拮抗剂，例如，在治疗精神疾病，焦虑和恶心和呕吐方面有用。