3-[1-(1-naphthyl)-2-nitroethyl]-1H-indole | 1114931-11-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-[1-(1-naphthyl)-2-nitroethyl]-1H-indole
• 英文别名: 3-(1-(naphthalen-1-yl)-2-nitroethyl)-1H-indole；3-(1-naphthalen-1-yl-2-nitroethyl)-1H-indole
• CAS: 1114931-11-1
• 化学式: C₂₀H₁₆N₂O₂
• 分子量: 316.359
• InChiKey: SQQATVNBDIJWBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-萘甲醛 在 cobalt(II) chloride hexahydrate 、 ammonium acetate 作用下， 反应 0.5h， 生成 3-[1-(1-naphthyl)-2-nitroethyl]-1H-indole
  参考文献：
  名称：

  金属卤化物水合物作为路易斯酸催化剂，用于吲哚和活性烯烃的共轭弗里德工艺反应

  摘要：

  研究了金属卤化物水合物如SnCl2·2H2O，MnCl2·4H2O，SrCl2·6H2O，CrCl2·6H2O，CoCl2·6H2O和CeCl3·7H2O作为温和的路易斯酸催化剂，用于吲哚和活性烯烃之间的共轭Friedel-Crafts反应。反应在室温下用脂族不饱和酮在几天内进行，而查耳酮仅在回流条件下反应。与硝基苯乙烯的反应在溶剂中或在无溶剂条件下进行。在所有情况下，均获得了合理至良好的产量。

  DOI：

  10.1590/s0103-50532011000400003

文献信息

• An efficient class of bis-NHC salts: applications in Pd-catalyzed reactions under mild reaction conditions
  作者：Chien-Cheng Chiu、Hui-Tzu Chiu、Dong-Sheng Lee、Ta-Jung Lu

  DOI：10.1039/c8ra04094j

  日期：——

  (bis-NHC) salts that can be easily made from commercially available and inexpensive starting materials. The application of these salts to Pd-catalyzed reactions is described. The palladium (Pd) catalyst generated in situ was highly effective under mild reaction conditions.

  这项研究描述了一类有效的双-N-杂环卡宾 (bis-NHC) 盐，可以很容易地由市售且廉价的起始材料制成。描述了这些盐在 Pd 催化反应中的应用。原位生成的钯 (Pd) 催化剂在温和的反应条件下非常有效。
• Synthesis of 9,9′-biphenanthryl-10,10′-bis(oxazoline)s and their preliminary evaluations in the Friedel–Crafts alkylations of indoles with nitroalkenes
  作者：Shuang-zheng Lin、Tian-pa You

  DOI：10.1016/j.tet.2008.11.083

  日期：2009.1

  Chiral 9,9′-biphenanthryl-10,10′-bis(oxazoline)s 6a–d were firstly prepared. These new chiral compounds were evaluated as ligands for the Friedel–Crafts alkylations of indoles with nitroalkenes, excellent yields and modest to good enantioselectivities were achieved.

  首先制备了手性9,9'-联菲基-10,10'-双（恶唑啉）s 6a – d。这些新的手性化合物被评估为吲哚与硝基烯烃的Friedel-Crafts烷基化反应的配体，获得了优异的收率和中等至良好的对映选择性。
• Preparation of a chiral Pt₁₂ tetrahedral cage and its use in catalytic Michael addition reaction
  作者：Imtiyaz Ahmad Bhat、Anthonisamy Devaraj、Prodip Howlader、Ki-Whan Chi、Partha Sarathi Mukherjee

  DOI：10.1039/c8cc01487f

  日期：——

  The reaction of chiral cis-[(1S,2S)-dch]Pt(NO3)2 (M) [where (1S,2S)-dch = (1S,2S)-1,2-diaminocyclohexane] with a hexadentate ligand (L) in 3 : 1 stoichiometric ratio yielded a [12+4] self-assembled chiral M12L4 molecular tetrahedron (T). The cage T features an internal 3D nanocavity with large open ‘windows’, enabling it to catalyze Michael addition reactions of a series of nitrostyrene derivatives

  手性顺式-[（（1 S，2 S）-dch ] Pt（NO 3）2（M）[[（1 S，2 S）-dch =（1 S，2 S）-1,2-具有六齿配体（L）的化学计量比为3的二氨基环己烷]产生[12 + 4]自组装的手性M 12 L 4分子四面体（T）。笼子T 具有内部3D纳米腔体，并带有开大的“窗口”，使其能够在9：1的水：甲醇混合物中催化一系列硝基苯乙烯衍生物与吲哚的迈克尔加成反应。
• Asymmetric Friedel−Crafts Alkylations of Indoles with Nitroalkenes Catalyzed by Zn(II)−Bisoxazoline Complexes
  作者：Yi-Xia Jia、Shuo-Fei Zhu、Yun Yang、Qi-Lin Zhou

  DOI：10.1021/jo0516537

  日期：2006.1.1

  A novel asymmetric Friedel−Crafts alkylation of indoles with nitroalkenes catalyzed by Zn(II)−bisoxazoline complexes has been developed. The nitroalkylated indoles are synthesized in excellent yields and high enantioselectivities (up to 90% ee). The effects of ligand structure, metal salt, and solvent on the reaction are discussed. The substrates of the reaction can be aromatic, heteroaromatic, and

  已经开发了一种新型的不对称的吲哚与Zn（II）-双恶唑啉配合物催化的硝基烯烃的弗里德-克来夫特烷基化反应。硝基烷基化的吲哚以优异的产率和高对映选择性（高达90％ee）合成。讨论了配体结构，金属盐和溶剂对反应的影响。反应的底物可以是芳族，杂芳族，甚至是脂肪族硝基烯烃。该反应的高反应性和选择性据推测归因于通过1，3-金属键合模型由硝基烯烃底物配位的手性路易斯酸的活化和不对称诱导。
• Simple and Efficient<i>Friedel-Crafts</i>Alkylation of 1<i>H</i>-Indole with Electron-Deficient Alkenes Promoted by Zinc Acetate
  作者：Harshadas Mitaram Meshram、Dachepally Aravind Kumar、Bandi Chennakesava Reddy

  DOI：10.1002/hlca.200800410

  日期：2009.5

  Abstractmagnified imageAn efficient method for the Friedel–Crafts alkylation of 1H‐indole with nitro alkenes in the presence of zinc acetate is described. The procedure is applicable to a variety of nitro alkenes and substituted indoles, and the yields are very high.