(R)-3-(1-(2,6-dichlorophenyl)-2-nitroethyl)-1H-indole | 1567948-81-5

• 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: (R)-3-(1-(2,6-dichlorophenyl)-2-nitroethyl)-1H-indole
• 英文别名: 3-[(1R)-1-(2,6-dichlorophenyl)-2-nitroethyl]-1H-indole
• CAS: 1567948-81-5
• 化学式: C₁₆H₁₂Cl₂N₂O₂
• 分子量: 335.189
• InChiKey: ZHLPRBAPBFXWKC-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  吲哚 、 反-2,6-二氯-β-硝基苯乙烯 在 (S)-4-isopropyl-2-(3-((S)-4-isopropyl-1-(4-methoxyphenyl)-4,5-dihydro-1H-imidazol-2-yl)pentan-3-yl)-4,5-dihydrooxazole 、 zinc trifluoromethanesulfonate 作用下， 以 甲苯 为溶剂， 反应 36.0h， 以81%的产率得到(R)-3-(1-(2,6-dichlorophenyl)-2-nitroethyl)-1H-indole
  参考文献：
  名称：

  Highly enantioselective Friedel–Crafts alkylation of indole with electron deficient trans-β-nitroalkenes using Zn(II)–oxazoline–imidazoline catalysts

  摘要：

  The catalytic asymmetric Friedel-Crafts alkylation of indole with trans-beta-nitroolefins has been developed via the catalysis of Zn(II)-oxazoline-imidazoline complexes. The reaction furnished nitroalkylated indoles in excellent yields (up to 95%) and with high enantioselectivities (up to 99% ee). The effects of solvent, temperature, the metal-triflate, and the ligand structure on the reaction are discussed. The substrates of the reaction can be substituted aromatic nitroolifins. The higher reactivity and enantioselectivity of the reaction could be due to the activation and asymmetric induction of chiral Lewis acids coordinated by the nitroolefin through a 1,3-metal bonded intermediate. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.11.018

文献信息

• Exploiting the Chiral Ligands of Bis(imidazolinyl)- and Bis(oxazolinyl)thiophenes—Synthesis and Application in Cu-Catalyzed Friedel–Crafts Asymmetric Alkylation
  作者：Mohammad Shahidul Islam、Abdullah Saleh Alammari、Assem Barakat、Saeed Alshahrani、Matti Haukka、Abdullah Mohammed Al-Majid

  DOI：10.3390/molecules26237408

  日期：——

  Five new C2-symmetric chiral ligands of 2,5-bis(imidazolinyl)thiophene (L1–L3) and 2,5-bis(oxazolinyl)thiophene (L4 and L5) were synthesized from thiophene-2,5-dicarboxylic acid (1) with enantiopure amino alcohols (4a–c) in excellent optical purity and chemical yield. The utility of these new chiral ligands for Friedel–Crafts asymmetric alkylation was explored. Subsequently, the optimized tridentate

  2,5-双（咪唑啉基）噻吩（L1 – L3）和2,5-双（恶唑啉基）噻吩（L4和L5）的五个新的C 2 -对称手性配体由噻吩-2,5-二羧酸合成（1 ) 与具有优异光学纯度和化学产率的对映纯氨基醇 ( 4a – c )。探索了这些新手性配体在 Friedel-Crafts 不对称烷基化中的应用。随后，优化的三齿配体L5和 Cu(OTf) 2催化剂（15 mol%）在甲苯中放置 48 小时，以中等至良好的产率（高达 76%）和良好的对映选择性（高达 81% ee）促进了 Friedel-Crafts 不对称烷基化。的双（恶唑啉基）噻吩配体的比更有效的双（咪唑啉基）为弗里德尔-克拉夫茨不对称烷基化的不对称诱导噻吩类似物。
• Highly enantioselective Friedel–Crafts alkylation of indole with electron deficient trans-β-nitroalkenes using Zn(II)–oxazoline–imidazoline catalysts
  作者：Mohammad Shahidul Islam、Abdullah M.A. Al Majid、Zeid Abdullah Al-Othman、Assem Barakat

  DOI：10.1016/j.tetasy.2013.11.018

  日期：2014.2

  The catalytic asymmetric Friedel-Crafts alkylation of indole with trans-beta-nitroolefins has been developed via the catalysis of Zn(II)-oxazoline-imidazoline complexes. The reaction furnished nitroalkylated indoles in excellent yields (up to 95%) and with high enantioselectivities (up to 99% ee). The effects of solvent, temperature, the metal-triflate, and the ligand structure on the reaction are discussed. The substrates of the reaction can be substituted aromatic nitroolifins. The higher reactivity and enantioselectivity of the reaction could be due to the activation and asymmetric induction of chiral Lewis acids coordinated by the nitroolefin through a 1,3-metal bonded intermediate. (C) 2013 Elsevier Ltd. All rights reserved.