1,2-dimethyl-3-(2-nitro-1-phenyl-ethyl)-indole | 108240-32-0

• 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-dimethyl-3-(2-nitro-1-phenyl-ethyl)-indole
• 英文别名: 1,2-Dimethyl-3-(2-nitro-1-phenyl-aethyl)-indol；1,2-Dimethyl-3-(2-nitro-1-phenylethyl)indole
• CAS: 108240-32-0
• 化学式: C₁₈H₁₈N₂O₂
• 分子量: 294.353
• InChiKey: ITTWIKMRNZKJTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  50.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1,2-二甲基吲哚 、 反式硝基苯乙烯 在 indium(III) bromide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.17h， 以92%的产率得到1,2-dimethyl-3-(2-nitro-1-phenyl-ethyl)-indole
  参考文献：
  名称：

  A Practical Indium Tribromide Catalysed Addition of Indoles to Nitroalkenes in Aqueous Media

  摘要：

  吲哚与亚硝基烯烃的1,4-缀加反应在水相中高效进行，使用了催化量的溴化铟（5摩尔%）。通过对同一催化剂进行连续循环反应，测试了溴化铟的重复使用性。

  DOI：

  10.1055/s-2002-31970

文献信息

• Quantification of Catalytic Activity for Electrostatically Enhanced Thioureas via Reaction Kinetics and UV–vis Spectroscopic Measurement
  作者：Yang Fan、Curtis Payne、Steven R. Kass

  DOI：10.1021/acs.joc.8b01552

  日期：2018.9.21

  Charged thiourea derivatives containing one and two methylated or octylated pyridinium ion centers and a tetraarylborate or triflate counteranion are reported. These novel catalysts are much more active in the Friedel–Crafts reactions of trans-β-nitroalkenes with N-methylindoles than the privileged N,N′-bis(3,5-bis(trifluoromethyl)phenyl)thiourea (i.e., Schreiner’s thiourea) by up to 2–3 orders of

  据报道，带电荷的硫脲衍生物含有一个和两个甲基化或辛基化吡啶鎓离子中心和一个四芳基硼酸酯或三氟甲磺酸酯抗衡阴离子。这些新型催化剂在反式-β-硝基烯烃与N-甲基吲哚的Friedel-Crafts反应中比特权的N，N'-双（3,5-双（三氟甲基）苯基）硫脲（即Schreiner硫脲）具有更高的活性。最多增加2–3个数量级。Kozlowski等人先前报道的紫外可见光谱法。被利用来合理化它们的反应顺序以及不带电的类似物。这些结果通过引入带正电荷的中心而不添加额外的N–H，OH–或S–H氢键供体位点，为有机催化剂提供了一种新的设计策略。
• Half-sandwich complexes of osmium containing guanidine-derived ligands
  作者：Amie Parker、Pilar Lamata、Fernando Viguri、Ricardo Rodríguez、José A. López、Fernando J. Lahoz、Pilar García-Orduña、Daniel Carmona

  DOI：10.1039/d0dt02713h

  日期：——

  react with AgSbF6 rendering the cationic aqua complexes [(η6-p-cymene)Os(H2L)(OH2)][SbF6]2 (H2L = H2L1 (4), H2L2 (5)). Addition of monodentate ligands L to compound 4 affords complexes of formula [(η6-p-cymene)Os(H2L1)L][SbF6]2 (L = py (6), 4-(NHMe)py (7), CO (8), P(OMe)3 (9)). Treatment of complexes 4 and 5 with NaHCO3 renders the monocationic complexes [(η6-p-cymene)Os(κ3N,N′,N′′-HL1)][SbF6] (10)

  式的吡啶基和phOSphano胍配合物[（η 6 - p -cymene）OSCL（ħ 2大号）] [的SbF 6 ]（对伞花烃=的MeC 6 H ^ 4的iPr; ħ 2大号= Ñ，Ñ双（p -Tolyl）-N ''-（2-吡啶基甲基）胍，H 2 L1（1）和N，N'-双（p -Tolyl）-N ''-（2-二苯基膦酰基乙基）胍，H 2 L2（2））已经从二聚物制备[（η 6 - p -cymene）OSCL} 2（μ-Cl）的2 ]和ħ 2大号在NaSbF的存在6。的复杂治疗2用HCl呈现phOSphano-胍络合物[（η 6 - p -cymene）OSCL 2（ħ 3大号2）] [的SbF 6 ]（3）。化合物1和2与AgSbF反应6呈现阳离子水性络合物[（η 6 - p -cymene）OS（H 2 L）（OH 2）] [SbF 6 ] 2（H 2 L＝H 2 L1（4），H 2
• Mechanism of the Alkylation of Indoles with Nitrostyrenes Catalyzed by Chiral-at-Metal Complexes
  作者：María Carmona、Ricardo Rodríguez、Vincenzo Passarelli、Daniel Carmona

  DOI：10.1021/acs.organomet.8b00925

  日期：2019.2.25

  Chiral-at-metal rhodium(III) complexes of the formula [Rh(κ4C,N,N′,P-L)A(Solv)][SbF6]n (Solv = A = MeCN, n = 2 (1); Solv = H2O, A = MeCN, n = 2 (2); Solv = MeCN, A = Cl, n = 1 (3); Solv = H2O, A = Cl, n = 1 (4)) catalyze the Friedel–Crafts reaction of trans-β-nitrostyrene and N-methyl-2-methylindole. Complex 4 reacts with trans-β-nitrostyrene, affording [RhCl(κ4C,N,N′,P-L)(trans-β-nitrostyrene)]+ (5)

  手性在金属铑（III）式的[Rh（κ的复合物4 C，N，N ' ，P -大号）A（SOLV）] [的SbF 6 ] Ñ（SOLV = A = MeCN中，Ñ = 2（1）; Solv = H 2 O，A = MeCN，n = 2（2）; Solv = MeCN，A = Cl，n = 1（3）; Solv = H 2 O，A = Cl，n = 1（4））催化反式-β-硝基苯乙烯与N-甲基-2-甲基吲哚的Friedel-Crafts反应。配合物4与反式反应-β硝基苯乙烯，得到[的RhCl（κ 4 C，N，N ' ，P -大号）（反式-β-硝基苯乙烯）] +（5）。在存在Ñ甲基-2-甲基吲哚，复杂5可逆地给出的混合物ACI硝基复合物6在高非对映选择性，这反过来，演变到通过1,3- prototropy的FC加合物由水分子介导的。基于实验NMR研究和DFT计算，提出了烷基化反应的详细机理途径，包括对所测对映体比率的来源的解释。
• Bottom-Up Assembly of a Highly Efficient Metal–Organic Framework for Cooperative Catalysis
  作者：Changda Li、Haitong Tang、Yu Fang、Zhifeng Xiao、Kunyu Wang、Xiang Wu、Helin Niu、Chengfeng Zhu、Hong-cai Zhou

  DOI：10.1021/acs.inorgchem.8b02434

  日期：2018.11.5

  In this study, we demonstrate a bottom-up assembly of a monomeric copper complex and a two-dimensional (2-D) heterometallic metal-organic framework (MOF) from a carboxylate-functionalized tridentate Schiff base ligand and metal ions. The obtained 2-D MOF features a unique bimetallic copper center which is different from its monometallic precursor and acts as an efficient heterogeneous catalyst for the Friedel-Crafts reaction and Henry reaction. The MOF catalyst shows a remarkably superior activity compared to its homogeneous counterparts in a wide range of substrates. It is presumably ascribed to the dual activation of the substrates by the active bimetallic copper center confined in the MOF network, which is supported by the significant changes in catalytic activity at low catalyst/substrates ratios when using the 2-D MOF and its precursor as catalysts, respectively. Moreover, the MOF catalyst also shows an excellent stability and recyclability. Our work, therefore, provides a stepwise strategy to design a heterogeneous cooperative catalyst, by taking advantage of the modulated structure of MOF and tunable functionality of the tridentate Schiff base, with high performance in a variety of organic synthesis.
• A combination of water and microwave irradiation promotes the catalyst-free addition of pyrroles and indoles to nitroalkenes
  作者：Margherita De Rosa、Annunziata Soriente

  DOI：10.1016/j.tet.2010.02.055

  日期：2010.4

  A combination of water and microwave irradiation was used for the first time to perform a catalyst-free nitro-Michael addition of pyrroles and indoles. Under superheated conditions, the water trends to ionize by changing its chemical and physical properties. Therefore, we performed a new green-protocol using the water either as environmentally no harm solvent or as catalyst. The reaction success is independent from the kind of pyrrole, indole or nitroalkenes rapidly affording the corresponding adducts and giving excellent yields. (C) 2010 Elsevier Ltd. All rights reserved.