1,3-bis(4-chlorophenyl)-3-(1H-indol-3-yl)propan-1-one | 1027736-81-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 1,3-bis(4-chlorophenyl)-3-(1H-indol-3-yl)propan-1-one
• CAS: 1027736-81-7
• 化学式: C₂₃H₁₇Cl₂NO
• 分子量: 394.3
• InChiKey: SBEQWSOFEZQFOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  32.9
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-氯苯甲醛 、 对氯苯乙酮 在 1.5C₂₀H₃₆N₄O₆S₂⁽²⁺⁾*Mo₁₂O₄₀P^(3-) 作用下， 以 neat (no solvent) 为溶剂， 反应 3.0h， 生成 1,3-bis(4-chlorophenyl)-3-(1H-indol-3-yl)propan-1-one
  参考文献：
  名称：

  亚甲基桥双阳离子-SO3H功能化咪唑鎓磷钼酸盐杂化物一锅连续合成3-取代吲哚的催化活性研究

  摘要：

  在此，我们的目的是合成三种有机-无机杂化物（DILPOM-1/2/3），该杂化物是由具有可变亚甲基连接间隔基的-SO 3 H-功能化二价咪唑鎓离子液体与无机12组装而成。 -钼磷酸。杂化物 DILPOM-1/2/3 是 2-甲基-1-(3-(2-甲基-3-磺基-1H-咪唑-3-鎓-1-基)丙基)-3-磺基-1H-咪唑磷钼酸-3-鎓，2-甲基-1-(4-(2-甲基-3-磺基-1H-咪唑-3-鎓-1-基)丁基)-3-磺基-1H-咪唑-3-鎓磷钼酸和2-甲基-1-(12-(2-甲基-3-磺基-1H-咪唑-3-鎓-1-基)十二烷基)-3-磺基-1H-咪唑-3-鎓磷钼酸根。热重分析证实，不同长度的连接间隔物的结合使得它们的热稳定性窗口更宽，因此它们可以用作高温反应中的有效催化剂。 –SO 3 H 基团和 PMo 12 O 40 3− 阴离子内氢键相互作用的程度战略性地控制了酸性位点与亚甲基键一起为杂

  DOI：

  10.1039/d4nj00353e

文献信息

• Acidic Ionic Liquid–Catalyzed Highly Efficient Reaction of Indoles to α,β‐Unsaturated Ketones
  作者：Da‐gong Gu、Shun‐jun Ji、Hong‐xia Wang、Qiu‐yan Xu

  DOI：10.1080/00397910701866304

  日期：2008.3.28

  Abstract A novel method for the Michael reaction of indoles to α,β‐unsaturated ketones catalyzed by acidic ionic liquid is reported. We obtained the corresponding products in excellent yields in the presence of [hmim]HSO4. Development of this method has resulted in a new protocol for the synthesis of β‐indolylketones.

  摘要 报道了一种酸性离子液体催化吲哚与α,β-不饱和酮迈克尔反应的新方法。我们在 [hmim]HSO4 存在下以极好的收率获得了相应的产品。这种方法的发展导致了合成 β-吲哚基酮的新方案。
• Al(OTf)3 Catalysed Friedel-Crafts Michael Type Addition of Indoles to α,β-Unsaturated Ketones with PEG-200 as Recyclable Solvent
  作者：Mukut Gohain、Jc Jacobs、Charlene Marais、Barend C. B. Bezuidenhoudt

  DOI：10.1071/ch13254

  日期：——

  An Al(OTf)3 catalysed efficient Friedel–Crafts Michael type addition of indoles to α,β-unsaturated ketones using recyclable PEG-200 as an alternative reaction solvent is disclosed. The reaction under microwave irradiation is clean, leads to excellent yields in minutes and reduces the use of volatile organic compounds.

  公开了使用可回收的PEG-200作为替代反应溶剂的Al（OTf）3催化的吲哚向α，β-不饱和酮的高效Friedel-Crafts Michael型加成反应。微波辐射下的反应是干净的，可在数分钟内获得优异的收率，并减少了挥发性有机化合物的使用。
• Calix[6]Arene Sulfonic Acids Catalysed Michael Reactions of Indoles with α,β-Unsaturated Ketones in Water Assisted by Microwave Radiation
  作者：Yuanyuan Xie、Linfeng Mao、Lehuan Li

  DOI：10.3184/174751913x13734725288804

  日期：2013.8

  Michael reactions of indoles with α,β-unsaturated ketones were carried out under microwave irradiation in water, affording the corresponding products in good to excellent yields. The calix[6]arene sulfonic acids bearing pendent aliphatic chains, as efficient surfactant-type acid catalysts, can be recovered after simple work-up and reused directly several times without loss of catalytic activity.

  在微波辐照下，在水中进行了吲哚与 α、β-不饱和酮的迈克尔反应，以良好到极佳的收率得到了相应的产物。带有下垂脂肪族链的钙[6]炔磺酸作为高效的表面活性剂型酸催化剂，经过简单的加工就可回收，并可直接重复使用多次而不会丧失催化活性。
• Synthesis and in vitro cytotoxicity study of 3-(1H-indol-3-yl)-1,3-diphenylpropan-1-ones
  作者：Jagadeesh N. Masagalli、Kittappa M. Mahadevan、Honnali Jayadevappa、Hosanagara N. Harishkumar、Rajesha Ganalu、Prashantha Nagaraja

  DOI：10.1007/s00044-013-0875-y

  日期：2014.6

  A series of 3-(1H-indol-3-yl)-1,3-diphenylpropan-1-ones 3a-l were synthesized in good to excellent yield by Michael addition of indole 1 with alpha,beta-unsaturated ketones 2a-l in presence of indium(III) sulphate (20 mol%). The structure of the title compounds were established by H-1 NMR, C-13 NMR, mass and elemental analysis. All the synthesized compounds were evaluated for in vitro cytotoxicity against five different cancer cell lines such as ACHN (human kidney adenocarcinoma), Panc1 (pancreatic), Calu1 (lung), H460 (non small cell lung), HCT116 (human colon cancer cell) and MCF10A (normal breast epithelium) using propidium iodide staining assay protocol. The result showed that the compounds 3e and 3l have excellent cytotoxic activity with the IC50 value ranging from 1.4-2.7 to 2.4-3.4 mu M, respectively, in comparison with the other compounds, Flavopiridol and Gemcitabine were employed as a positive control. The findings conferred 3-(1H-indol-3-yl)-1,3-diphenylpropan-1-ones seem to be promising candidates for the development of new anticancer drugs.