1H-吲哚,1-[(4-甲基苯基)磺酰]-3-(3-羰基-1-丁烯基)-,(E)- | 122244-55-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1H-吲哚,1-[(4-甲基苯基)磺酰]-3-(3-羰基-1-丁烯基)-,(E)-
• 英文名称: (3E)-4-{1-[(4-methylphenyl)sulfonyl]-1H-indol-3-yl}but-3-en-2-one
• 英文别名: 3-(N-tosylindolylidene)acetone；(E)-4-[1-(4-methylphenyl)sulfonylindol-3-yl]but-3-en-2-one
• CAS: 122244-55-7
• 化学式: C₁₉H₁₇NO₃S
• 分子量: 339.415
• InChiKey: LVXDIYCWXOHUEN-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  1H-吲哚,1-[(4-甲基苯基)磺酰]-3-(3-羰基-1-丁烯基)-,(E)- 在 对甲苯磺酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 乙酸乙酯 、 甲苯 为溶剂， 反应 72.0h， 生成 methyl 4-(acetyloxy)-2-{1-[(4-methylphenyl)sulfonyl]-1H-indol-3-yl}benzoate
  参考文献：
  名称：

  （杂）芳基取代的苯基的可扩展多组分合成：专注于无金属的卤代联芳基，3-Arylindoles和异鸟氨酸A的合成

  摘要：

  在压力金属容器中完成了（杂）亚芳基丙酮的简单，可扩展且无金属的多组分烯醇乙酰化反应，然后与丙酸甲酯进行了Diels-Alder热反应。环加合物中间体的芳构化得到相应的官能化的（杂）联芳基。

  DOI：

  10.1002/ejoc.201901551
• 作为产物：
  描述：

  3-(3-Oxobutylidene)indole 、 对甲苯磺酰氯 在 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 60.0h， 以88%的产率得到1H-吲哚,1-[(4-甲基苯基)磺酰]-3-(3-羰基-1-丁烯基)-,(E)-
  参考文献：
  名称：

  Highly Selective Diels−Alder Reactions of Dienophiles with 1,3-Cyclohexadiene Mediated by Yb(OTf)₃·2H₂O and Ultrahigh Pressures

  摘要：

  [GRAPHICS]Ultrahigh pressures and catalytic Yb(OTf)(3). 2H(2)O were found to mediate Diets-Alder reactions of various electron-deficient dienophiles with 1,3-cyclohexadiene to produce endo-bicyclo[2.2.2]oct-2-enes in moderate to excellent yield and selectivity. The proposed total synthesis of hapalindole Q based on bicyclo[2.2.2]oct-2-ene construction by Diels-Alder reaction and subsequent olefin cleavage is outlined, Preliminary results demonstrating the viability of this strategy are presented.

  DOI：

  10.1021/ol0065773

文献信息

• Photoredox-Nickel Dual-Catalyzed <i>C</i>-Alkylation of Secondary Nitroalkanes: Access to Sterically Hindered α-Tertiary Amines
  作者：Sina Rezazadeh、Maxwell I. Martin、Raphael S. Kim、Glenn P. A. Yap、Joel Rosenthal、Donald A. Watson

  DOI：10.1021/jacs.2c13174

  日期：2023.3.1

  The preparation of tertiary nitroalkanes via the nickel-catalyzed alkylation of secondary nitroalkanes using aliphatic iodides is reported. Previously, catalytic access to this important class of nitroalkanes via alkylation has not been possible due to the inability of catalysts to overcome the steric demands of the products. However, we have now found that the use of a nickel catalyst in combination

  据报道，通过使用脂肪族碘化物对仲硝基烷烃进行镍催化烷基化来制备叔硝基烷烃。此前，由于催化剂无法克服产物的空间需求，通过烷基化催化获得这一类重要的硝基烷烃是不可能的。然而，我们现在发现，将镍催化剂与光氧化还原催化剂和光结合使用会产生活性更高的烷基化催化剂。这些现在可以接触叔硝基烷烃。这些条件是可扩展的以及耐空气和耐湿气的。重要的是，叔硝基烷产物的还原可以快速获得α-叔胺。
• Organo‐Catalyzed Enantioselective [4+2] Annulation of Glutaraldehyde and C3‐Indolyl‐imines To Access Indol‐3‐yl‐piperidines
  作者：Anoop Singh、Imtiaz A. Shah、Jyothi Yadav、Preetika Sharma、Rajni Kant、Eldhose Iype、Sravendra Rana、Indresh Kumar

  DOI：10.1002/ejoc.202300901

  日期：2023.12

  A simple and straightforward method is developed for the enantioselective synthesis of indol‐3‐yl‐piperidine. The reaction proceeds through a proline‐catalyzed direct Mannich reaction between glutaraldehyde and C3‐indolyl‐imines, followed by intramolecular reductive cyclization as an overall [4+2] annulation in one‐pot fashion. A series of indol‐3‐yl‐piperidine have been accessed with good yields up to 71 % and high enantioselectivity up to >99 % ee.

  摘要 开发了一种简单直接的方法，用于对映体选择性合成吲哚-3-基哌啶。该反应通过脯氨酸催化戊二醛和 C3-吲哚基亚胺之间的直接曼尼希反应进行，然后进行分子内还原环化，以单锅方式进行整体[4+2]环化。我们获得了一系列吲哚-3-基哌啶，收率高达 71%，对映体选择性高达 99%。
• METAL POLYSULFIDE-COMPLEX WITH BIOLOGICAL AND CHEMICAL ACTIVITY
  申请人：Carrizo-Manzanero Ricardo

  公开号：US20120207854A1

  公开（公告）日：2012-08-16

  Aqueous solution, cream, hydrogel or spray composition containing compound Sn-On-Xn; where S(n=5-8), O (n=3-7) and X═Fe, Cr or Ni, and most effectively, S7-O4-Fe4 as active ingredient for cutaneous, intradermal and subcutaneous treatment of dermo-epithelial lesions, comprising but not limited to, certain types of skin cancer (basal cell, keratocanthoma and spinocellular carcinomas), conjunctivitis, folliculitis, acne, gingivitis, stomatitis, fungal, dermatomycosis, parasitosis, condylomatosis, balanitis, vaginitis, vaginosis, bacteriosis and endometriosis; by reducing the number of infecting microorganism, not limited to Candida sp., Actinobacillus actinomycetemcomitans, Pseudomonas sp., Porphyromonas gingivalis., Escherichia , sp., Staphyloccocus sp. Streptococcus sp., Herpes simplex I, Herpes simplex II, Coxackievirus A and B, Echovirus, Varicella Zoster (HHV-3), Human Papilloma Virus Gardnerella Vaginalis, Trichomonas vaginalis, Corynebacterium sp., present on the body skin and mucosas. Treating condition may include other abnormal conditions of the skin and epithelium, including insect bites, leukoplakia, oral (aphthous) ulcers and burns, trauma, aphthous, herpervirus infections, stomatitis, herpangina (mouth blisters), a painful mouth infection caused by coxsackieviruses.
• Highly Selective Diels−Alder Reactions of Dienophiles with 1,3-Cyclohexadiene Mediated by Yb(OTf)₃·2H₂O and Ultrahigh Pressures
  作者：Aaron C. Kinsman、Michael A. Kerr

  DOI：10.1021/ol0065773

  日期：2000.11.1

  [GRAPHICS]Ultrahigh pressures and catalytic Yb(OTf)(3). 2H(2)O were found to mediate Diets-Alder reactions of various electron-deficient dienophiles with 1,3-cyclohexadiene to produce endo-bicyclo[2.2.2]oct-2-enes in moderate to excellent yield and selectivity. The proposed total synthesis of hapalindole Q based on bicyclo[2.2.2]oct-2-ene construction by Diels-Alder reaction and subsequent olefin cleavage is outlined, Preliminary results demonstrating the viability of this strategy are presented.
• Scalable Multicomponent Synthesis of (Hetero)aryl-Substituted Phenyls: Focus on Metal-Free Halogenated Biaryls, 3-Arylindoles, and Isourolithine A Synthesis
  作者：Andrea Temperini、Daniela Lanari、Francesco Colognese、Francesca Piazzolla

  DOI：10.1002/ejoc.201901551

  日期：2019.12.19

  A simple, scalable and metal‐free multicomponent enol acetylation of (hetero)arylidene acetones followed by a thermal Diels‐Alder reaction with methyl propiolate was accomplished in a pressure metal vessel. Aromatization of the cycloadduct intermediates yielded the corresponding functionalised (hetero)biaryls.

  在压力金属容器中完成了（杂）亚芳基丙酮的简单，可扩展且无金属的多组分烯醇乙酰化反应，然后与丙酸甲酯进行了Diels-Alder热反应。环加合物中间体的芳构化得到相应的官能化的（杂）联芳基。