3-benzoyl-1-(phenylsulfonyl)indole | 80360-19-6

• 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
• 英文名称: 3-benzoyl-1-(phenylsulfonyl)indole
• 英文别名: phenyl(1-(phenylsulfonyl)-1H-indol-3-yl)methanone；(Phenyl)(1-phenylsulfonyl-1H-indol-3-yl)methanone；[1-(benzenesulfonyl)indol-3-yl]-phenylmethanone
• CAS: 80360-19-6
• 化学式: C₂₁H₁₅NO₃S
• 分子量: 361.421
• InChiKey: QPSDXUKJJFVCOV-UHFFFAOYSA-N

物化性质

• 沸点：
  579.7±42.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  64.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-benzoyl-1-(phenylsulfonyl)indole 在 potassium carbonate 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 以88%的产率得到3-苯甲酰基吲哚
  参考文献：
  名称：

  A convenient synthesis of 3-acylindoles via Friedel Crafts acylation of 1-(phenylsulfonyl)indole. A new route to pyridocarbazole-5,11-quinones and ellipticine

  摘要：

  DOI：

  10.1021/jo00350a001
• 作为产物：
  描述：

  吲哚 在 正丁基锂 、 碘 、 叔丁基锂 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 9.5h， 生成 3-benzoyl-1-(phenylsulfonyl)indole
  参考文献：
  名称：

  Generation and reactions of 3-lithio-1-(phenylsulfonyl)indole

  摘要：

  DOI：

  10.1021/jo00344a001

文献信息

• Radical Beckmann Rearrangement and Its Application in the Formal Total Synthesis of Antimalarial Natural Product Isocryptolepine via C–H Activation
  作者：Pankaj S. Mahajan、Vivek T. Humne、Subhash D. Tanpure、Santosh B. Mhaske

  DOI：10.1021/acs.orglett.6b01634

  日期：2016.7.15

  ketoximes, mediated by ammonium persulfate-dimethyl sulfoxide as a reagent, has been achieved under neutral conditions. Based on the radical trapping and 18O-labeling experiments, the transformation follows a mechanism involving a radical pathway. The scope and generality of the developed protocol has been demonstrated by 19 examples. The developed protocol and Pd-catalyzed intramolecular double C–H

  由过硫酸铵-二甲基亚砜作为试剂介导的酮肟的贝克曼重排已在中性条件下完成。基于自由基捕获和18 O-标记实验，转化遵循涉及自由基途径的机制。所开发协议的范围和通用性已通过19个示例得到了证明。已开发的方案和Pd催化的分子内双C–H双重活化被用作抗疟疾天然产物异隐油菜醇的正式总合成中的关键步骤。
• Synthesis of vinylindoles and vinylpyrroles by the Peterson olefination or by use of the Nysted reagent
  作者：Wayland E. Noland、Christopher L. Etienne、Nicholas P. Lanzatella

  DOI：10.1002/jhet.313

  日期：2011.3

  Vinylindoles and vinylpyrroles were prepared from their corresponding aldehydes or ketones using the Peterson olefination, or by use of the Nysted reagent, a commercially available gem‐dimetallic compound. The two methods provide efficient and convenient access to these useful heterocyclic 1,3‐diene systems. J. Heterocyclic Chem., (2011).

  乙烯基吲哚和乙烯基吡咯是使用Peterson烯烃或相应的市售宝石-双金属化合物Nysted试剂，由其相应的醛或酮制得的。两种方法可有效便捷地访问这些有用的杂环1,3-二烯系统。J.杂环化​​学。（2011）。
• Room-Temperature Decarboxylative Couplings of α-Oxocarboxylates with Aryl Halides by Merging Photoredox with Palladium Catalysis
  作者：Wan-Min Cheng、Rui Shang、Hai-Zhu Yu、Yao Fu

  DOI：10.1002/chem.201502286

  日期：2015.9.14

  Enabled by merging iridium photoredox catalysis and palladium catalysis, α‐oxocarboxylate salts can be decarboxylatively coupled with aryl halides to generate aromatic ketones and amides at room temperature. DFT calculations suggest that this reaction proceeds through a Pd0–PdII–PdIII pathway, in which the PdIII intermediate is responsible for reoxidizing IrII to complete the IrIII–*IrIII–IrII photoredox

  通过合并铱的光氧化还原催化和钯催化，α-氧代羧酸盐可以与芳基卤化物脱羧偶联，在室温下生成芳族酮和酰胺。DFT计算表明，该反应通过Pd 0 -Pd II -Pd III途径进行，其中Pd III中间体负责重新氧化Ir II以完成Ir III- * Ir III -Ir II光氧化还原循环。
• Metal-Free Activation of DMF by Dioxygen: A Cascade Multiple-Bond-Formation Reaction to Synthesize 3-Acylindoles from 2-Alkenylanilines
  作者：Ji-Bo Wang、Yin-Long Li、Jun Deng

  DOI：10.1002/adsc.201700584

  日期：2017.10.4

  cascade C−N, C−C and C−O multiple‐bond‐formation reaction to synthesize 3‐acylindoles from 2‐alkenylanilines with DMF (N,N‐dimethylformamide) as a one‐carbon synthon is described. This approach employed dioxygen as a terminal oxidant and oxygen donor, generally provided the 3‐acylindoles in moderate to good yields. Moreover, the mechanistic investigation unambiguously revealed that the 2‐carbon of 3‐acylindole

  描述了一种级联的C，C和C的多键形成反应，以2烯基苯胺与DMF（N，N-二甲基甲酰胺）作为单碳合成子合成3-酰基环。该方法采用双氧作为末端氧化剂和氧供体，通常以中等至良好的产率提供3-酰基环。此外，机理研究清楚地表明，3-丙烯腈的2-碳源自DMF的N-甲基。
• Catalytic Asymmetric Nucleophilic Addition of 3-Vinyl Indoles to Imines
  作者：Jia-Hui Xue、Ming Shi、Feng Yu、Xiao-Yun Li、Wen Ren、Li-Na Fu、Qi-Xiang Guo

  DOI：10.1021/acs.orglett.6b01880

  日期：2016.8.5

  The 3-vinyl indole is used as a nucleophile to react with aromatic and aliphatic imines. Chiral 3-substituted indoles bearing multiple functional groups are produced with up to 99% yield, a 98:2 E/Z ratio, and 97% ee. A possible mechanism is proposed to explain the observed stereoselectivities. This strategy provides an efficient way for the preparation of novel chiral 3-substituted indoles.

  3-乙烯基吲哚用作亲核试剂与芳族和脂族亚胺反应。制备具有多个官能团的手性3-取代的吲哚，产率高达99％，E / Z比为98：2 ，ee为97％。提出了一种可能的机制来解释观察到的立体选择性。该策略为制备新型手性3-取代的吲哚提供了有效的方法。