2-苯基-6,7-二氢-1氢-吲哚-4(5氢)-酮 | 14006-77-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 2-苯基-6,7-二氢-1氢-吲哚-4(5氢)-酮
• 英文名称: 2-phenyl-6,7-dihydro-1H-indol-4(5H)-one
• 英文别名: 2-phenyl-1,5,6,7-tetrahydroindol-4-one
• CAS: 14006-77-0
• 化学式: C₁₄H₁₃NO
• 分子量: 211.263
• InChiKey: IOCKGQRVMMIOHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  32.9
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  2-苯基-6,7-二氢-1氢-吲哚-4(5氢)-酮 在 钯 作用下， 以 二苯醚 为溶剂， 生成 2-phenyl-1H-indol-4-ol
  参考文献：
  名称：

  Piperidino-propanols

  摘要：

  本发明涉及新型吡啶基丙醇，特别是式子中的1-(3-杂环氧基-2-羟基-丙醇)-4-(N-杂环基)-吡啶。其中R.sub.1是取代或未取代的杂环芳基基团，R.sub.2是氢或取代或未取代的脂肪、环脂肪、环脂肪-脂肪或芳基脂肪基团或酰基，而alk是将两个氮原子相隔2或3个碳原子的低级烷基，或者是取代或未取代的1,2-苯基基团，以及其盐。还涉及制备这些化合物的方法，以及含有这些化合物的药物制剂及其用途，特别是作为降压剂、抗心动过速剂和α-肾上腺素能抑制剂的药物制剂。

  公开号：

  US04264599A1
• 作为产物：
  描述：

  (4-oxo-2-phenyl-1,5,6,7-tetrahydroindol-5-yl) acetate 以40%的产率得到
  参考文献：
  名称：

  OIKAWA Y.; YONEMITSU O., HETEROCYCLES, 1977, 8, SPEC. ISSUE, 307-312

  摘要：

  DOI：

文献信息

• Nitrogen Fixation: Synthesis of Heterocycles Using Molecular Nitrogen as a Nitrogen Source
  作者：Miwako Mori、Masaya Akashi、Masanori Hori、Katsutoshi Hori、Mayumi Nishida、Yoshihiro Sato

  DOI：10.1246/bcsj.77.1655

  日期：2004.9

  Nitrogen fixation using transition metals is a fascinating process. We have already reported on the incorporation of molecular nitrogen into organic compounds using a titanium–nitrogen complex reported by Yamamoto. We developed a novel titanium-catalyzed nitrogenation procedure using TiCl4 in the presence of an excess amount of Li and TMSCl. In this reaction, a 1 atm pressure of nitrogen gas can be used and the reaction proceeds at room temperature. The procedure is very simple. A THF solution of TiCl4 or Ti(OiPr)4 (1 equiv.), Li (10 equiv.), and TMSCl (10 equiv.) was stirred under an atmosphere of nitrogen at room temperature overnight to give titanium–nitrogen complexes. Although the structures of the titanium–nitrogen complexes have not yet been determined, they would consist of N(TMS)3, X2TiN(TMS)2, and XTi=NTMS. Using this procedure, various heterocycles, such as indole, quinoline, pyrrole, pyrrolizine, and indolizine derivatives, could be synthesized from molecular nitrogen in good-to-moderate yields as a stoichiometric reaction based on a titanium complex by a one-pot reaction. Furthermore, monomorine I and pumiliotoxin C were synthesized from molecular nitrogen as a nitrogen source. This procedure was further extended for the syntheses of heterocycles using a catalytic amount of titanium complex; also, indole and pyrrole derivatives were obtained in high yields.

  过渡金属固氮是一个迷人的过程。我们之前已经报道过使用Yamamoto报道的钛-氮配合物将分子氮引入有机化合物的方法。我们开发了一种新的钛催化氮化过程，使用TiCl4在过量Li和TMSCl的存在下进行。在这种反应中，可以使用1大气压的氮气，反应在室温下进行。这个过程非常简单。将TiCl4或Ti(OiPr)4（1 equiv.）、Li（10 equiv.）和TMSCl（10 equiv.）的THF溶液在氮气气氛下在室温下搅拌过夜，得到钛-氮配合物。尽管钛-氮配合物的结构尚未确定，但它们可能由N(TMS)3、X2TiN(TMS)2和XTi=NTMS组成。使用这种方法，可以通过钛配合物作为定量反应的单锅反应，以良好至中等的收率合成各种杂环化合物，如吲哚、喹啉、吡咯、吡咯啉和吲哚啉衍生物。此外，使用分子氮作为氮源合成了monomorine I和pumiliotoxin C。这种方法进一步扩展，用于使用催化量的钛配合物合成杂环化合物；此外，以高收率获得了吲哚和吡咯衍生物。
• Versatile Synthesis of 2-(Substituted phenyl)-6,7-dihydro-1H-indol-4(5H)-ones from Morita-Baylis-Hillman Acetates of 2-Oxo-2-(substituted phenyl)acetaldehyde
  作者：Harikrishna Batchu、Sanjay Batra

  DOI：10.1002/ejoc.201200107

  日期：2012.5

  A versatile synthesis of 2-(substituted phenyl)-6,7-dihydro-1H-indol-4(5H)-ones from adducts of the Morita–Baylis–Hillman reaction between 2-oxo-2-(substituted phenyl)acetaldehydes and cyclohex-2-enone under mild conditions is described.

  从 Morita-Baylis-Hillman 反应的加合物合成 2-(取代苯基)-6,7-dihydro-1H-indol-4(5H)-ones 和 2-oxo-2-(取代苯基)乙醛和描述了温和条件下的环己-2-烯酮。
• Efficient synthesis of pyrroles and 4,5,6,7-tetrahydroindoles via palladium-catalyzed oxidation of hydroxy-enamines
  作者：Yutaka Aoyagi、Toshihiko Mizusaki、Masahiro Shishikura、Takashi Komine、Tokuji Yoshinaga、Haruko Inaba、Akihiro Ohta、Koichi Takeya

  DOI：10.1016/j.tet.2006.06.070

  日期：2006.9

  Facile and one-pot synthetic route of poly-substituted pyrroles and 4-oxo-4,5,6,7-tetrahydroindoles is established, which consists of three steps: (1) palladium-catalyzed oxidation of hydroxy-enamines by using tetrakis(triphenylphosphine)palladium and mesityl bromide oxidation system, (2) intramolecular cyclization, and (3) dehydration.

  建立了多取代的吡咯和4-oxo-4,5,6,7-四氢吲哚的简便，一锅合成路线，该路线包括三个步骤：（1）钯催化的四胺氧化羟基烯胺（三苯基膦）钯和异丁基溴的氧化系统，（2）分子内环化和（3）脱水。
• Characterization of heterogeneous aryl–Pd(<scp>ii</scp>)–oxo clusters as active species for C–H arylation
  作者：Taeil Shin、Minjun Kim、Younjae Jung、Sung June Cho、Hyunwoo Kim、Hyunjoon Song

  DOI：10.1039/d0cc06716d

  日期：——

  C–H arylation with heterogeneous palladium was investigated. The surface oxidation of Pd nanoparticles with a hypervalent iodine reagent, [Ph2I]BF4, resulted in the generation of Pd(II)–aryl–oxo clusters, which were characterized as the crucial intermediate.

  研究了C-H与异质钯的芳基化。高价碘试剂[Ph 2 I] BF 4对Pd纳米颗粒的表面氧化导致生成Pd（II）-芳基-氧代簇，这是关键的中间体。
• On the Reaction of<i>N</i>-[(3-Oxo-2-cyclohexenyl)imino]triphenylphosphorane with α-Bromo Ketones and α,β-Unsaturated Ketones
  作者：Makoto Nitta、Hironobu Soeda、Yukio Iino

  DOI：10.1246/bcsj.63.932

  日期：1990.3

  The thermal reaction of N-[(3-oxo-2-cyclohexenyl)imino]triphenylphosphorane with α-bromo ketones and α,β-unsaturated ketones underwent an enamine-type alkylation and a subsequent aza-Wittig reaction to give substituted 1,5,6,7-tetrahydro-4H-indol-4-ones and 7,8-dihydro-5(6H)-quinolinones albeit in modest yields.

  N-[(3-oxo-2-cyclohexenyl)imino]triphenylphosphorane 与 α-溴酮和 α,β-不饱和酮的热反应经历了烯胺型烷基化和随后的氮杂-Wittig 反应，得到取代的 1,5 ,6,7-四氢-4H-indol-4-ones 和 7,8-dihydro-5(6H)-quinolinones 尽管产率适中。