1-(2,3-dihydrocyclopenta[b]indol-4(1H)-yl)ethanone | 99391-35-2

• 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: 1-(2,3-dihydrocyclopenta[b]indol-4(1H)-yl)ethanone
• 英文别名: 1-(2,3-dihydro-1H-cyclopenta[b]indol-4-yl)ethanone
• CAS: 99391-35-2
• 化学式: C₁₃H₁₃NO
• 分子量: 199.252
• InChiKey: ADRYZJPIYVMUQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 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-(2,3-dihydrocyclopenta[b]indol-4(1H)-yl)ethanone 在 二甲基硫 、 氧气 、 tetraphenylporphyrin 作用下， 以 氘代氯仿 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 1-Acetylcyclopent<2,3>indole 2,3-epoxide
  参考文献：
  名称：

  Oxidation of N-Acylindoles by Dimethyldioxirane and Singlet Oxygen: Substituent Effects on Thermally Persistent Indole Epoxides and Dioxetanes

  摘要：

  Photooxygenation of the N-acylindoles 1a-d afforded the labile indole dioxetanes 2 and the relatively stable allylic hydroperoxides 3. The dioxetanes 2a,c,d were sufficiently stable for isolation and spectral characterization. Additionally, they were characterized by chemical transformations, namely reduction to the indole epoxides 5 by dimethyl sulfide, acid-catalyzed rearrangement to allylic hydroperoxides 3c,d, and thermolysis to the cleavage products 4. Oxidation of the N-acylindoles I with dimethyldioxirane afforded the epoxides 5, which were characterized on the basis of their spectral data and chemical transformations to the 2-indolinones 6 and 2-methyleneindoline 7. These decomposition products (except 7e) were fully characterized. The stability of the epoxides 5 depended on the substitution type, i.e., the carbazole epoxide 5c decomposed already at temperatures above ca. -50 degrees C, whereas the cyclopentindole epoxide 5b was stable at 20 degrees C for days. The latter was unequivocally characterized by X-ray analysis.

  DOI：

  10.1021/jo00089a016
• 作为产物：
  描述：

  N-(2-(2-oxocyclopentyl)phenyl)acetamide 在 iron(III) chloride 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以87%的产率得到1-(2,3-dihydrocyclopenta[b]indol-4(1H)-yl)ethanone
  参考文献：
  名称：

  分子内合作Ç ？1,3-二羰基化合物与2-碘苯胺的C键裂解反应生成邻（N-酰基氨基）芳基酮和多取代的吲哚

  摘要：

  铜-催化Ç 与2- iodoanilines 1,3-二羰基化合物C键裂解反应被开发。在此过程中，邻位效应在反应性中起着重要作用，并且通过时程HRMS分析可以清楚地观察到涉及（2-氨基苯基）-双-（1,3-二羰基）铜物种的新反应途径。反应混合物。与以前的报道不同，1,3-二羰基化合物的亲核和亲电子部分都通过CC键裂解与2-碘苯胺偶联形成邻-（N-酰基氨基）芳基酮，可以有效地转化为多取代基吲哚。

  DOI：

  10.1002/chem.201500272

文献信息

• Electrochemical Dearomative 2,3-Difunctionalization of Indoles
  作者：Ju Wu、Yingchao Dou、Régis Guillot、Cyrille Kouklovsky、Guillaume Vincent

  DOI：10.1021/jacs.8b13371

  日期：2019.2.20

  oxidative dearomatization of indoles leading to 2,3-dialkoxy or 2,3-diazido indolines under undivided conditions at a constant current. This operationally simple electro-oxidative procedure avoids the use of an external oxidant and displays excellent functional group compatibility. The formation of the two C-O or C-N bonds is believed to arise from the oxidation of the indoles into radical cation intermediates

  我们报告了使用电化学对吲哚进行直接氧化脱芳构化，在恒定电流下在未分开的条件下产生 2,3-二烷氧基或 2,3-二叠氮二氢吲哚。这种操作简单的电氧化程序避免了使用外部氧化剂并显示出优异的官能团兼容性。两个 CO 或 CN 键的形成被认为是由吲哚氧化成自由基阳离子中间体引起的。
• Pd‐Catalyzed Dearomatization of Indole Derivatives <i>via</i> Intermolecular Heck Reactions ^†
  作者：Ping Yang、Ren‐Qi Xu、Chao Zheng、Shu‐Li You

  DOI：10.1002/cjoc.201900509

  日期：2020.3

  Pd‐catalyzed intermolecular dearomative Heck reaction of indoles with aryl iodides is described. The challenges on both reactivity and regioselectivity are addressed by the judicious regulation of the geometric and electronic properties of the substrates. An array of indoline derivatives bearing C2‐quaternary center is obtained in good to excellent yields (up to 93%) with exclusive regioselectivity

  描述了Pd催化的吲哚与芳基碘化物的分子间脱芳香性Heck反应。通过对底物的几何和电子性质的明智调节来应对反应性和区域选择性方面的挑战。在操作简单的条件下，可以获得一系列具有C2-季中心的二氢吲哚衍生物，收率好至极好（高达93％），并且具有唯一的区域选择性。机械建议由详细的DFT计算支持。
• Perhydroxylation of Indole Derivatives by Osmium Tetroxide
  作者：D. W. OCKENDEN、K. SCHOFIELD

  DOI：10.1038/168603a0

  日期：1951.10

  ole (I) have recently aroused some interest1. The related compound (II) does not undergo Wagner–Meerwein rearrangements like those given by (I)2. Witkop1a has satisfactorily explained this failure by pointing out that such rearrangement of (II) would involve the formation of a four-membered ring compound. While this suggestion is convincing, it seemed worth while to confirm that the diols (I) and (II)

  9-乙酰基-10 : 11-二羟基六氢咔唑 (I) 所经历的各种转变最近引起了一些兴趣。相关化合物 (II) 不会像 (I)2 给出的那样经历 Wagner-Meerwein 重排。Witkop1a 通过指出（II）的这种重排将涉及四元环化合物的形成，令人满意地解释了这种失败。虽然这个建议令人信服，但似乎值得确认二醇 (I) 和 (II) 具有相似的构型，因为 Wagner-Meerwein 变化显着受所涉及化合物的顺式或反式构型的影响，只有顺式二醇变得容易重新排列3。此外，(I)和(II)迄今已通过相当不同的方法制备。
• Translating Planar Heterocycles into Three‐Dimensional Analogs by Photoinduced Hydrocarboxylation**
  作者：Myriam Mikhael、Sara N. Alektiar、Charles S. Yeung、Zachary K. Wickens

  DOI：10.1002/anie.202303264

  日期：2023.7.24

  We report a new strategy that translates indoles and related heterocycles into diverse 3D analogs by dearomative hydrocarboxylation. The transformation is highly chemoselective, broad in scope, operationally simple, and readily amenable to high-throughput experimentation (HTE).

  我们报告了一种新策略，通过脱芳烃加氢羧化将吲哚和相关杂环化合物转化为多种 3D 类似物。该转化具有高度化学选择性、范围广泛、操作简单且易于进行高通量实验（HTE）。
• Dearomative Diallylation of <i>N</i>-Acylindoles Mediated by FeCl₃
  作者：Ju Wu、Raj Kumar Nandi、Régis Guillot、Cyrille Kouklovsky、Guillaume Vincent

  DOI：10.1021/acs.orglett.8b00361

  日期：2018.4.6

  Three-dimensional indolines possessing two contiguous-stereogenic centers were obtained stereoselectively via the FeCl3-mediated dearomative introduction of two allyl groups to N-acylindoles with allyltrimethylsilane. Synthetic transformations allowed obtention of trans-tetrahydrocarbazoles and an aza[4.4.3]propellane scaffold by RCM. Selective hydration of one of the allyl groups was also achieved.